Editing Chicago (band) (section)

== Group history ==

=== The Big Thing ===
The group now known as Chicago began on February 15, 1967, at a meeting involving saxophonist [[Walter Parazaider]], guitarist [[Terry Kath]], drummer [[Danny Seraphine]], trombonist [[James Pankow]], trumpet player [[Lee Loughnane]], and keyboardist/singer [[Robert Lamm]]. Kath, Parazaider, and Seraphine had played together previously in two other groups—Jimmy Ford and the Executives, and the Missing Links.<ref name="Seraphine"/>{{rp|29–49}} Parazaider had met Pankow and Loughnane when they were all students at [[DePaul University]].<ref name="Seraphine"/>{{rp|48–49}} Lamm, a student at [[Roosevelt University]],<ref>{{Cite news|url=https://chicago.cbslocal.com/2016/02/14/robert-lamm-founding-member-of-chicago-looks-back-on-bands-history-ahead-of-rock-hall-of-fame-induction/|title=Robert Lamm, Founding Member Of Chicago, Looks Back On Band's History Ahead Of Rock Hall Of Fame Induction|last=Williams|first=Jim|date=February 14, 2016|work=CBSChicago|access-date=July 3, 2018|language=en|archive-url=https://web.archive.org/web/20180703220356/https://chicago.cbslocal.com/2016/02/14/robert-lamm-founding-member-of-chicago-looks-back-on-bands-history-ahead-of-rock-hall-of-fame-induction/|archive-date=July 3, 2018|url-status=live}}</ref> was recruited from his group, Bobby Charles and the Wanderers.<ref name="Seraphine"/>{{rp|49}} The group of six called themselves the Big Thing, and like most other groups playing in Chicago nightclubs, played Top 40 hits. Realizing the need for both a [[tenor]] to complement [[baritone]]s Lamm and Kath, and a bass player because Lamm's use of organ bass pedals did not provide "adequate bass sound", local tenor and bassist [[Peter Cetera]] was invited to join the Big Thing in late 1967.<ref name="Ruhlmannp1">{{cite AV media notes|title= Chicago Group Portrait (Box Set)|year= 1991|url= http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_1.html|page= 1|access-date= January 29, 2016|first= William James|last= Ruhlmann|format= CD booklet archived online|publisher= Columbia Records|location= New York City, NY|archive-url= https://web.archive.org/web/20160214052811/http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_1.html|archive-date= February 14, 2016|url-status=live|df= mdy-all}}</ref><ref name="Seraphine"/>{{rp|58–59}}

=== Chicago Transit Authority and early success ===
[[File:Chicago Transit Authority (Chicago) circa 1969.jpg|thumb|Chicago Transit Authority circa 1969]]
While gaining some success as a cover band, the group began working on original songs. In June 1968, at manager [[James William Guercio]]'s request, the Big Thing moved to [[Los Angeles]], [[California]],<ref>{{Cite book|title=Street Player: My Chicago Story|last=Seraphine|first=Danny|publisher=John Wiley & Sons Inc.|year=2011|isbn=9780470416839|page=65}}</ref> where they signed with [[Columbia Records]] and changed their name to Chicago Transit Authority.<ref name="allmusic" /> While performing on a regular basis at the [[Whisky a Go Go]] nightclub in [[West Hollywood, California|West Hollywood]], the band got exposure to more famous musical artists of the time,<ref>{{Cite book|title=Street Player: My Chicago Story|last=Seraphine|first=Danny|publisher=John Wiley & Sons Inc.|year=2011|isbn=9780470416839|page=77}}</ref> subsequently opening for [[Janis Joplin]] and [[Jimi Hendrix]].<ref name="Seraphine">{{Cite book|last=Seraphine|first=Danny|year=2011|title=Street Player: My Chicago Story|publisher=John Wiley & Sons, Inc.|isbn=978-0-470-41683-9}}</ref>{{rp|77–78,106–107}}<ref name="Ruhlmannp3">{{cite AV media notes|title= Chicago Group Portrait (Box Set)|year= 1991|url= http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_3.html|page= 3|access-date= January 29, 2016|first= William James|last= Ruhlmann|format= CD booklet archived online|publisher= Columbia Records|location= New York City, NY|archive-url= https://web.archive.org/web/20160213201745/http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_3.html|archive-date= February 13, 2016|url-status=live|df= mdy-all}}</ref> Group biographer William James Ruhlmann recorded Walt Parazaider as saying that Jimi Hendrix once told him: {{" '}}Jeez, your horn players are like one set of lungs and your guitar player is better than me.{{' "}}<ref name="Ruhlmannp3" />

Their first record (April 1969), ''[[Chicago Transit Authority (album)|Chicago Transit Authority]]'', is a double album, a rarity for a band's initial studio release. The album made it to No. 17 on the [[Billboard 200|''Billboard'' 200]] album chart,<ref name= "Chicago Billboard 200" /> sold over one million copies by 1970, and was awarded a [[music recording sales certification|platinum disc]].<ref name="The Book of Golden Discs">{{cite book|first=Joseph|last=Murrells|year=1978|title=The Book of Golden Discs|edition=2nd|publisher=Barrie and Jenkins Ltd|location=London|pages=[https://archive.org/details/bookofgoldendisc00murr/page/255 255–256]|isbn=0-214-20512-6|url-access=registration|url=https://archive.org/details/bookofgoldendisc00murr/page/255|access-date=December 17, 2019|archive-url=https://web.archive.org/web/20191215064643/https://archive.org/details/bookofgoldendisc00murr/page/255|archive-date=December 15, 2019|url-status=live}}</ref> The album included a number of pop-rock songs – "[[Does Anybody Really Know What Time It Is?]]", "[[Beginnings (Chicago song)|Beginnings]]", "[[Questions 67 and 68]]", and "[[I'm a Man (The Spencer Davis Group song)|I'm a Man]]" – which were later released as singles. For this inaugural recording effort the group was nominated for a [[Grammy Award]] for 1969 [[Grammy Award for Best New Artist|Best New Artist of the Year]].<ref name="grammy awards Chicago">{{cite web|url=https://www.grammy.com/grammys/artists/chicago|title=Grammy Awards: Chicago|publisher=The Recording Academy|access-date=September 25, 2017|archive-url=https://web.archive.org/web/20190320024210/https://www.grammy.com/grammys/artists/chicago|archive-date=March 20, 2019|url-status=live}}</ref> In 2025, the Library of Congress selected ''Chicago Transit Authority'' for inclusion as an album in the National Recording Registry.<ref>{{Cite web |title=National Recording Registry Inducts Sounds of Elton John, Chicago, Broadway's 'Hamilton,' Mary J. Blige, Amy Winehouse, Minecraft and Microsoft |url=https://newsroom.loc.gov/news/national-recording-registry-inducts-sounds-of-elton-john--chicago--broadway-s--hamilton---mary-j.-bl/s/986b2312-27dd-4b66-bd41-3113e0cb2e57 |access-date=2025-04-14 |website=Library of Congress - News and Content for Media |language=en}}</ref>

According to Cetera, the band was booked to perform at [[Woodstock]] in 1969, but promoter [[Bill Graham (promoter)|Bill Graham]], with whom they had a contract, exercised his right to reschedule them to play at the [[Fillmore West]] on a date of his choosing, and he scheduled them for the Woodstock dates. [[Santana (band)|Santana]], which Graham also managed, took Chicago's place at Woodstock,<ref>{{Cite news|url=http://www.spokesman.com/stories/2008/sep/21/cetera-lends-voice-to-superpops-opener/|title=Cetera lends voice to SuperPops opener|last=Kershner|first=Jim|date=September 21, 2008|work=The Spokesman-Review|access-date=November 2, 2017|language=en|archive-url=https://web.archive.org/web/20171107010527/http://www.spokesman.com/stories/2008/sep/21/cetera-lends-voice-to-superpops-opener/|archive-date=November 7, 2017|url-status=live}}</ref> and that performance is considered to be Santana's "breakthrough" gig.<ref>{{Cite news|url=http://somethingelsereviews.com/2015/08/15/santana-woodstock-gregg-rolie/|title=Gregg Rolie remembers Santana breakthrough at Woodstock|last=Deriso|first=Nick|date=August 15, 2015|work=Something Else!|access-date=November 2, 2017|language=en-US|archive-url=https://web.archive.org/web/20171107005918/http://somethingelsereviews.com/2015/08/15/santana-woodstock-gregg-rolie/|archive-date=November 7, 2017|url-status=live}}</ref> A year later, when he needed to replace headliner Joe Cocker, and then Cocker's intended replacement, Jimi Hendrix, Graham booked Chicago to perform at [[Tanglewood]], which has been called a "pinnacle" performance by Concert Vault.<ref>{{Cite press release|author=<!--Staff writer(s); no by-line.-->|title=Concert Vault Restores Pinnacle Moment In Rock History|url=https://www.prnewswire.com/news-releases/concert-vault-restores-pinnacle-moment-in-rock-history-193586011.html|date=February 27, 2013|publisher=Concert Vault|agency=PR Newswire|language=en|access-date=November 2, 2017|archive-url=https://web.archive.org/web/20171107021220/https://www.prnewswire.com/news-releases/concert-vault-restores-pinnacle-moment-in-rock-history-193586011.html|archive-date=November 7, 2017|url-status=live}}</ref>

After the release of their first album, the band's name was shortened to Chicago to avoid legal action being threatened by the [[Chicago Transit Authority|actual mass-transit company of the same name]].<ref name= Ruhlmannp3/>

=== 1970s: ''Chicago'' ===
[[File:Chicago band 1973.jpg|thumb|upright=1.25|Chicago circa 1973]]
In 1970, less than a year after its first album, the band released a second album, titled ''[[Chicago (album)|Chicago]]'' (retroactively known as ''Chicago II''), which is another double-LP. The album's centerpiece track is a seven-part, 13-minute [[suite (music)|suite]] composed by Pankow called "[[Ballet for a Girl in Buchannon]]". The suite yielded two top ten hits: "[[Make Me Smile]]" (No.&nbsp;9 U.S.) and "[[Colour My World (Chicago song)|Colour My World]]",<ref name= BBChicagoHot100 /> both sung by Kath. Among the other tracks on the album: Lamm's dynamic but cryptic "[[25 or 6 to 4]]" (Chicago's first Top 5 hit),<ref name=BBChicagoHot100 /> which is a reference to a songwriter trying to write at 25 or 26 minutes before 4 o'clock in the morning,<ref>{{cite interview|last=Lamm|first=Robert|subject-link=Robert Lamm|interviewer=Devon Maloney|title=Chicago Comes to Agganis|url=http://www.bu.edu/today/2009/chicago-comes-to-agganis/|work=BU Today|publisher=Boston University|location=Boston, Massachusetts, U.S.A.|date=June 15, 2009|access-date=February 13, 2017|quote=It's a reference to time. It's a song about writing the song, and I looked at my watch while I was writing and it was 25 minutes to four in the morning, or maybe 26.|archive-url=https://web.archive.org/web/20170214003435/http://www.bu.edu/today/2009/chicago-comes-to-agganis/|archive-date=February 14, 2017|url-status=live}}</ref><ref name="Seraphine" />{{rp|109}}<ref>{{Cite web|url=http://www.classicrockrevisited.com/show_interview.php?id=949|title=CRR Interview – Chicago's Lee Loughnane: Feelin' Stronger Everyday|last=Wright|first=Jeb|publisher=classicrockrevisited.com|access-date=February 10, 2017|archive-url=https://web.archive.org/web/20170211081447/http://www.classicrockrevisited.com/show_interview.php?id=949|archive-date=February 11, 2017|url-status=live}}</ref> and was sung by Cetera with [[Terry Kath]] on guitar; the lengthy war-protest song "It Better End Soon"; and, at the end, Cetera's [[Apollo 11|1969 Moon landing]]-inspired "[[Where Do We Go from Here (Chicago song)|Where Do We Go from Here?]]"<ref name=Ruhlmannp4>{{cite AV media notes|title= Chicago Group Portrait (Box Set)|year= 1991|url= http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_4.html|page= 4|access-date= February 10, 2017|first= William James|last= Ruhlmann|format= CD booklet archived online|publisher= Columbia Records|location= New York City, NY|archive-url= https://web.archive.org/web/20171024112742/http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_4.html|archive-date= October 24, 2017|url-status=live|df= mdy-all}}</ref> The double-LP album's inner cover includes the playlist, the entire lyrics to "It Better End Soon", and two declarations: "This endeavor should be experienced sequentially", and, "With this album, we dedicate ourselves, our futures and our energies to the people of the revolution. And the revolution in all of its forms."<ref name= "Chicago album">{{Cite AV media notes |title=[[Chicago (album)]]|last=Chicago|year=1970 |type=Vinyl LP cover liner notes |publisher=Columbia |id=KGP 24 CS 9962 XSM 151734 |location=U.S.A. }}</ref> The album was a commercial success, rising to number four on the ''Billboard'' 200,<ref name= "Chicago Billboard 200" /> and was certified gold by the [[Recording Industry Association of America|Recording Industry Association of America (RIAA)]] in 1970, and platinum in 1991.<ref name="RIAA Gold & Platinum">{{Cite news|url=https://www.riaa.com/gold-platinum/|title=Gold & Platinum |work=RIAA|access-date=September 25, 2017|language=en-US|archive-url=https://web.archive.org/web/20190209113439/https://www.riaa.com/gold-platinum/?tab_active=default-award&ar=EMMYLOU+HARRIS&ti=ELITE+HOTEL|archive-date=February 9, 2019|url-status=live}}</ref> The band was nominated for two Grammy Awards as a result of this album, [[Grammy Award for Album of the Year|Album of the Year]] and [[Grammy Award for Best Pop Performance by a Duo or Group with Vocals|Best Contemporary Vocal Performance by a Duo, Group or Chorus]].<ref name="grammy awards Chicago" />

''[[Chicago III]]'', another double LP, was released in 1971 and charted at No. 2 on the ''Billboard'' 200.<ref name= "Chicago Billboard 200" /> Two singles were released from it: "[[Free (Chicago song)|Free]]" from Lamm's "Travel Suite", which charted at No. 20 on the [[Billboard Hot 100|''Billboard'' Hot 100]];<ref name= BBChicagoHot100 /> and "[[Lowdown (Chicago song)|Lowdown]]", written by Cetera and Seraphine, which made it to No. 35.<ref name= BBChicagoHot100 /> The album was certified gold by the RIAA in February 1971, and platinum in November 1986.<ref name="RIAA Gold & Platinum" />

The band released LPs at a rate of at least one album per year from their third album in 1971 on through the 1970s. During this period, the group's album titles primarily consisted of the band's name followed by a [[Roman numeral]], indicating the album's sequence in their canon. The exceptions to this scheme were the band's fourth album, a live [[box set|boxed set]] entitled ''[[Chicago at Carnegie Hall]]'', their twelfth album ''[[Hot Streets]]'', and the [[Arabic numeral|Arabic-numbered]] ''[[Chicago 13]]''. While the live album itself did not bear a number, the four discs within the set were numbered Volumes I through IV.

In 1971, the band released ''[[Chicago at Carnegie Hall]] Volumes I, II, III, and IV'', a quadruple LP, consisting of live performances, mostly of music from their first three albums, from a week-long run at [[Carnegie Hall]]. Chicago was the first rock act to sell out a week at Carnegie Hall and the live recording was made to chronicle that milestone.<ref name= Ruhlmannp5 /> Along with the four vinyl discs, the packaging contained some strident political messaging about how "We [youth] can change the System", including wall posters and voter registration information.<ref>{{cite news |title=the akron |newspaper=Los Angeles Times  |date=November 6, 1971 |page=6(Part 1)(advertisement) |url=https://www.newspapers.com/clip/14076637/the_los_angeles_times/ |via=[[Newspapers.com]] |access-date=September 25, 2017 |archive-url=https://web.archive.org/web/20170929232016/https://www.newspapers.com/clip/14076637/the_los_angeles_times/ |archive-date=September 29, 2017 |url-status=live  }}{{free access}}</ref><ref>{{cite news |last=Mendoza |first=Henry |title='Chicago at Carnegie Hall' Called Superb |newspaper=The San Bernardino County Sun |date=November 9, 1971 |page=A-13 |url=https://www.newspapers.com/clip/14078340/the_san_bernardino_county_sun/ |access-date=September 29, 2017 |via=[[Newspapers.com]] |archive-url=https://web.archive.org/web/20170929231940/https://www.newspapers.com/clip/14078340/the_san_bernardino_county_sun/ |archive-date=September 29, 2017 |url-status=live  }}{{free access}}</ref> The album went gold "out of the box" and on to multi-platinum status.<ref name= Ruhlmannp5 /> William James Ruhlmann says ''Chicago at Carnegie Hall'' was "perhaps" the best-selling box set by a rock act and held that record for 15 years.<ref name= Ruhlmannp5 /> In recognition of setting Carnegie Hall records and the ensuing four-LP live recordings, the group was awarded a ''Billboard'' 1972 Trendsetter Award.<ref name="Trendsetter Award">{{cite magazine|date=December 25, 1971|title=Talent in Action: Billboard 1972 Trendsetter Awards|magazine=Billboard|location=New York, NY|publisher=Billboard Publications, Inc.|volume=83|number=52|url=https://books.google.com/books?id=SQ8EAAAAMBAJ&pg=PA52|page=TA-4, TA-20|via=Google Books|access-date=October 20, 2017|archive-date=February 26, 2023|archive-url=https://web.archive.org/web/20230226055453/https://books.google.com/books?id=SQ8EAAAAMBAJ&pg=PA52|url-status=live}}</ref> Drummer Danny Seraphine attributes the fact that none of Chicago's first four albums were issued on single LPs to the productive creativity of this period and the length of the jazz-rock pieces.<ref>{{cite interview |last=Seraphine |first=Danny |subject-link=Danny Seraphine |interviewer=Tom Schulte |title=Danny Seraphine on Outsight Radio Hours |url=https://archive.org/download/SeraphineDannyOnORH |format=audio |publisher=Archive.org |date=September 22, 2013 |time=12:11 |access-date=November 3, 2013 |archive-url=https://web.archive.org/web/20190320024210/https://archive.org/download/SeraphineDannyOnORH |archive-date=March 20, 2019 |url-status=live  }}</ref>

In 1972, the band released its first single-disc release, ''[[Chicago V]]'', which reached No. 1 on both the ''[[Billboard (magazine)|Billboard]]'' pop<ref name= "Chicago Billboard 200" /> and jazz album charts.{{Citation needed|reason=Can't find this album on 1972 Billboard jazz album charts.|date=September 2017}} It features "[[Saturday in the Park (song)|Saturday in the Park]]", written by Robert Lamm, which mixes everyday life and political yearning in a more subtle way. It peaked at No.&nbsp;3 on the ''Billboard'' Hot 100 in early 1972.<ref>{{cite web|url=http://hitsofalldecades.com/chart_hits/index.php?option=com_content&task=view&id=2041&Itemid=52|title=Billboard Magazine (USA) Weekly Single Charts From 1972|website=Hits of All Decades|publisher=Designs with Hope|access-date=January 30, 2016|archive-url=https://web.archive.org/web/20160207045915/http://hitsofalldecades.com/chart_hits/index.php?option=com_content&task=view&id=2041&Itemid=52|archive-date=February 7, 2016|url-status=live}}</ref><ref>{{cite web|url=https://weeklytop40.wordpress.com/1972-all-charts/|title=1972: all charts|website=Weekly Top 40|date=December 31, 1972 |publisher=Eagle Media/JTMichaelson|access-date=January 30, 2016|archive-url=https://web.archive.org/web/20160308153829/https://weeklytop40.wordpress.com/1972-all-charts/|archive-date=March 8, 2016|url-status=live}}</ref> The second single released from the album was the Lamm-composed "[[Dialogue (Part I & II)]]", which featured a musical "debate" between a political activist (sung by Kath) and a blasé college student (sung by Cetera). It peaked at No. 24 on the Hot 100 chart.<ref name= BBChicagoHot100 />
[[File:Chicago 1975 press photo.jpg |thumb|right|upright=1.25|Chicago circa 1975.]]
Other albums and singles followed in each of the succeeding years. 1973's ''[[Chicago VI]]'' was the first of several albums to include Brazilian jazz percussionist [[Laudir de Oliveira]]<ref name=Ruhlmannp7/> and saw Cetera emerge as the main lead singer. According to William James Ruhlmann, de Oliveira was a "sideman" on ''Chicago VI'' and became an official member of the group in 1974.<ref name=Ruhlmannp7/> ''Chicago VI'' featured two top ten singles,<ref name="BBChicagoHot100" /> "[[Just You 'n' Me]]", written by Pankow, and "[[Feelin' Stronger Every Day]]", written by Pankow and Cetera. ''[[Chicago VII]]'' was the band's double-disc 1974 release. Three singles were released from this album: "[[(I've Been) Searchin' So Long]]", written by Pankow, and "[[Call on Me (Chicago song)|Call On Me]]", written by Loughnane, which both made it into the top ten;<ref name="BBChicagoHot100" /> and [[the Beach Boys]]-infused "[[Wishing You Were Here]]", written by Cetera, which peaked at number eleven.<ref name="BBChicagoHot100" /> Writing for ''Billboard'' magazine, [[Joel Whitburn]] reported in October 1974 that the group had seven albums, its entire catalog at the time, on the ''Billboard'' 200 simultaneously, placing them seventh in a list of artists in that category.<ref name=Whitburn /> Their 1975 release, ''[[Chicago VIII]]'', featured the political allegory "[[Harry Truman (song)|Harry Truman]]" (No. 13, Top 100 chart) and the nostalgic Pankow-composed "[[Old Days]]" (No. 5, Top 100 chart).<ref>{{cite web|url=https://weeklytop40.wordpress.com/1975-all-charts/|title=1975: all charts|website=Weekly Top 40|date=December 31, 1975 |publisher=Eagle Media/JTMichaelson|access-date=January 30, 2016|archive-url=https://web.archive.org/web/20160308192720/https://weeklytop40.wordpress.com/1975-all-charts/|archive-date=March 8, 2016|url-status=live}}</ref><ref>{{cite web|url=http://hitsofalldecades.com/chart_hits/index.php?option=com_content&task=view&id=2156&Itemid=52|title=Billboard Magazine (USA) Weekly Single Charts From 1975|website=Hits of All Decades|publisher=Designs with Hope|access-date=January 30, 2016|archive-url=https://web.archive.org/web/20160207045915/http://hitsofalldecades.com/chart_hits/index.php?option=com_content&task=view&id=2156&Itemid=52|archive-date=February 7, 2016|url-status=live}}</ref> That summer also saw a joint tour across America with the Beach Boys,<ref name=Ruhlmannp7>{{cite AV media notes|title=Chicago Group Portrait (Box Set)|year=1991|url=http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_7.html|page=7|access-date=January 29, 2016|first=William James|last=Ruhlmann|format=CD booklet archived online|publisher=Columbia Records|location=New York City, NY|archive-url=https://web.archive.org/web/20160213222057/http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_7.html|archive-date=February 13, 2016|url-status=live}}</ref> with the two acts performing separately, then coming together for a finale.<ref>{{Cite news|url=https://www.nytimes.com/1975/06/14/archives/chicago-and-the-beach-boys-combined.html|title=Chicago and the Beach Boys, Combined|last=Rockwell|first=John|date=June 14, 1975|work=[[The New York Times]]|access-date=August 23, 2017|language=en-US|issn=0362-4331|archive-url=https://web.archive.org/web/20170824052149/http://www.nytimes.com/1975/06/14/archives/chicago-and-the-beach-boys-combined.html|archive-date=August 24, 2017|url-status=live}}</ref> ''Chicago VI'', ''VII'', and ''VIII'' all made it to No. 1 on the ''Billboard'' 200,<ref name="Chicago Billboard 200" /> all were certified gold the years they were released, and all have since been certified platinum. ''Chicago VI'' was certified two times multi-platinum in 1986.<ref name="Gold & Platinum by Artist">{{Cite news|url=https://www.riaa.com/gold-platinum/?tab_active=awards_by_artist#search_section|title=Gold & Platinum - RIAA: Search by Artist|work=RIAA|access-date=July 26, 2017|language=en-US|archive-url=https://web.archive.org/web/20161216204505/http://www.riaa.com/gold-platinum/?tab_active=awards_by_artist#search_section|archive-date=December 16, 2016|url-status=live}}</ref> ''[[Chicago IX: Chicago's Greatest Hits]]'' was released in 1975 and became the band's fifth consecutive No. 1 album on the ''Billboard'' 200''.<ref name="Chicago Billboard 200" />''

1976's ''[[Chicago X]]'' features Cetera's ballad "[[If You Leave Me Now]]", which held the top spot in the U.S. charts for two weeks<ref>{{Cite news|url=https://www.billboard.com/archive/charts/1976/hot-100|title=The Hot 100 – 1976 Archive Charts Archive|newspaper=Billboard|access-date=February 9, 2017|archive-url=https://web.archive.org/web/20161126045038/http://www.billboard.com/archive/charts/1976/hot-100|archive-date=November 26, 2016|url-status=live}}</ref> and the UK charts for three weeks.<ref>{{Cite web|url=http://www.officialcharts.com/charts/singles-chart/19761107/7501/|title=Official Singles Chart Top 50 {{!}} Official Charts Company for Nov 7, 1976|website=www.officialcharts.com|access-date=February 9, 2017|archive-url=https://web.archive.org/web/20170211081240/http://www.officialcharts.com/charts/singles-chart/19761107/7501/|archive-date=February 11, 2017|url-status=live}}</ref> It was the group's first No. 1 single,<ref name= Ruhlmannp7 /> and won Chicago their only [[Grammy Award]] to date,<ref name="Grammy Winners Database">{{cite web|url=https://www.grammy.com/nominees/search?artist=Chicago&field_nominee_work_value=&year=All&genre=Al|title=Grammy Winners Database|publisher=National Academy of Recording Arts and Sciences|access-date=January 2, 2017|language=en-US|archive-url=https://web.archive.org/web/20190322031010/https://www.grammy.com/grammys/awards?artist=Chicago&field_nominee_work_value=&year=All&genre=Al|archive-date=March 22, 2019|url-status=live}}</ref> the 1976 [[Grammy Award for Best Pop Performance by a Duo or Group with Vocal|Best Pop Vocal Performance by a Duo, Group or Chorus]], at the [[19th Annual Grammy Awards]] held on February 19, 1977.<ref name="19th Annual Grammy Awards">{{cite web|url=http://www.grammy.com/awards/19th-annual-grammy-awards|title=19th Annual Grammy Awards|access-date=January 21, 2016|archive-url=https://web.archive.org/web/20160129081802/http://www.grammy.com/awards/19th-annual-grammy-awards|archive-date=January 29, 2016|url-status=live}}</ref> The single was certified gold by the RIAA the same year of its release.<ref>{{Cite news|url=https://www.riaa.com/gold-platinum/?tab_active=default-award&ar=CHICAGO&ti=IF+YOU+LEAVE+ME+NOW|title=Gold & Platinum - RIAA: If You Leave Me Now (single)|work=RIAA|access-date=September 24, 2017|language=en-US|archive-url=https://web.archive.org/web/20161022100139/http://www.riaa.com/gold-platinum/?tab_active=default-award&ar=Chicago&ti=If+You+Leave+Me+Now|archive-date=October 22, 2016|url-status=live}}</ref> The song almost did not make the cut for the album.<ref name= Ruhlmannp7 /> "If You Leave Me Now" was recorded at the last minute. The success of the song, according to William James Ruhlmann, foreshadowed a later reliance on ballads.<ref name= Ruhlmannp7 /> The album reached No. 3 on the ''Billboard'' 200,<ref name= "Chicago Billboard 200" /> was certified both gold and platinum by the RIAA the same year of its release and two times multi-platinum since,<ref>{{Cite news|url=https://www.riaa.com/gold-platinum/?tab_active=default-award&ar=CHICAGO&ti=CHICAGO+X |title=Gold & Platinum - RIAA: Chicago X|work=RIAA|access-date=September 24, 2017|language=en-US|archive-url=https://web.archive.org/web/20190715033619/https://www.riaa.com/gold-platinum/?tab_active=default-award&ar=CHICAGO&ti=CHICAGO+X|archive-date=July 15, 2019|url-status=live}}</ref> and was also nominated for the [[Grammy Award for Album of the Year]].<ref name="grammy awards Chicago" /> 1976 was the first year that albums were certified platinum by the RIAA.<ref>{{Cite news|url=https://www.thebalance.com/platinum-album-certification-explained-2460607|title=When Does an Album Actually Go Platinum?|last=McDonald|first=Heather|date=April 22, 2017|work=The Balance|access-date=December 7, 2017|language=en|archive-url=https://web.archive.org/web/20171208003709/https://www.thebalance.com/platinum-album-certification-explained-2460607|archive-date=December 8, 2017|url-status=live}}</ref> In honor of the group's platinum album achievement, Columbia Records that year awarded the group a 25-pound bar of pure platinum, made by [[Cartier (jeweler)|Cartier]].<ref name="Rolling Stone Platinum">{{cite news|last=Young|first=Charles M.|title=Random Notes: Rolling Stone: Capitol out of Lennon suit|newspaper=Tallahassee Democrat|date=December 8, 1976|page=26|url=https://www.newspapers.com/clip/15626604/tallahassee_democrat/|via=[[Newspapers.com]]|access-date=December 7, 2017|archive-url=https://web.archive.org/web/20171208004125/https://www.newspapers.com/clip/15626604/tallahassee_democrat/|archive-date=December 8, 2017|url-status=live}} {{free access}}</ref> (''Billboard'' magazine reported it as a 30-pound bar.)<ref name="Billboard photo">{{cite magazine|date=December 4, 1976|title=Platinum All the Way (photo caption)|magazine=[[Billboard (magazine)|Billboard]]|volume=88|issue=49|url=https://books.google.com/books?id=ASUEAAAAMBAJ&pg=PA14|page=4|access-date=December 6, 2017|via=Google Books|archive-date=February 26, 2023|archive-url=https://web.archive.org/web/20230226055453/https://books.google.com/books?id=ASUEAAAAMBAJ&pg=PA14|url-status=live}}</ref>{{refn|group=Note|name="Pt bar"|Although ''[[Rolling Stone]]'' reporter Charles M. Young wrote that Chicago was awarded the platinum bar because it was the first band to receive platinum album certification for Columbia Records,<ref name="Rolling Stone Platinum"/> this was not the case. ''Chicago X'' was certified platinum on September 4, 1976, but [[Aerosmith]]'s album, [[Rocks (Aerosmith album)|''Rocks'']], also on Columbia Records, was certified platinum on July 9, 1976, before it.<ref>{{cite web|url=https://www.riaa.com/gold-platinum/?tab_active=default-award&se=Aerosmith#search_section|title=Gold & Platinum: Aerosmith|website=RIAA|access-date=January 22, 2019|archive-url=https://web.archive.org/web/20160826014259/http://www.riaa.com/gold-platinum/?tab_active=default-award&se=Aerosmith#search_section|archive-date=August 26, 2016|url-status=live}}</ref><ref>{{cite magazine|title=Aerosmith's First Certified Platinum Album|date=July 24, 1976|magazine=Billboard|pages=12, 13 (Two page advertisement)|url=https://www.americanradiohistory.com/Archive-Billboard/70s/1976/Billboard%201976-07-24.pdf|access-date=January 22, 2019|via=americanradiohistory.com}}</ref> ''Billboard'' reported that the platinum bar was awarded in recognition of the group's ten platinum albums.<ref name="Billboard photo"/> ''Billboard''{{'}}s account seems more likely in consideration of the two-full-pages advertisement Columbia placed in the June 12, 1976, issue of ''Record World'' announcing, " 'Chicago X.' Their tenth platinum album, on Columbia records and tapes."<ref>{{cite magazine |title= America's favorite. Ask for it by name. |url=https://www.americanradiohistory.com/Archive-Record-World/70s/76/RW-1976-06-12.pdf#page=12/ |magazine=Record World| publisher=Bob Austin |pages=12–13 (Two-full-pages advertisement for ''Chicago X'') |date=June 12, 1976 |volume=32 |number=1512 |via=AmericanRadioHistory.com|access-date=March 18, 2019 }}</ref> The albums released prior to 1976, however, were not actually certified platinum by the RIAA until 1986.<ref>{{cite magazine|title=CBS gets Pre-1976 Certs: 132 Honors Issued|last=Grein|first=Paul|date=December 13, 1986|magazine=Billboard|url=https://books.google.com/books?id=ICUEAAAAMBAJ&pg=PA4|pages=4, 67|access-date=January 22, 2019|via=Google books|archive-date=February 26, 2023|archive-url=https://web.archive.org/web/20230226055453/https://books.google.com/books?id=ICUEAAAAMBAJ&pg=PA4|url-status=live}}</ref>}} At the [[American Music Awards of 1977|4th Annual American Music Awards]], a fan-voted awards show,<ref>{{Cite news|url=https://www.theamas.com/about/|title=About {{!}} American Music Awards|work=American Music Awards|access-date=October 2, 2017|language=en-US|archive-url=https://web.archive.org/web/20170901170315/https://www.theamas.com/about/|archive-date=September 1, 2017|url-status=live}}</ref> held January 31, 1977, Chicago won the award for [[American Music Award for Favorite Pop/Rock Band/Duo/Group|Favorite Pop/Rock Band/Duo/Group]], the group's first of two American Music Awards they have received.<ref name="AMA Winner Database">{{cite web|url=http://www.theamas.com/winners-database/?winnerKeyword=%22Chicago%22&winnerYear=&winnerCategory=|title=American Music Awards Winners Database|access-date=January 21, 2016|archive-url=https://web.archive.org/web/20160207045915/http://www.theamas.com/winners-database/?winnerKeyword=%22Chicago%22&winnerYear=&winnerCategory=|archive-date=February 7, 2016|url-status=live}}</ref>

The group's 1977 release, ''[[Chicago XI]]'', includes Cetera's ballad "[[Baby, What a Big Surprise]]", a No. 4 U.S. hit which became the group's last top 10 hit of the decade.<ref name=BBChicagoHot100 /> ''Chicago XI'' performed well commercially, peaking at No. 6 on the ''Billboard'' 200,<ref name= "Chicago Billboard 200" /> and reaching platinum status during the year of its release.<ref name="Gold & Platinum by Artist" /> On October 17, 1977, during the intermission of an [[Emerson, Lake & Palmer]] concert, [[Madison Square Garden]] announced its new [[Madison Square Garden Gold Ticket Award|Gold Ticket Award]], to be given to performers who had brought the venue over 100,000 in unit ticket sales.<ref name="BB Oct29_1977">{{cite magazine|date=October 29, 1977|title=Box Office Gold Ticket|magazine=Billboard|location=USA|publisher=Lee Zhito|volume=89|number=43|page=35|url=https://books.google.com/books?id=akUEAAAAMBAJ&pg=PA42|via=Google books|access-date=March 30, 2019|archive-date=February 26, 2023|archive-url=https://web.archive.org/web/20230226055454/https://books.google.com/books?id=akUEAAAAMBAJ&pg=PA42|url-status=live}}</ref><ref name="Cash Box Nov5_77">{{cite magazine |date=November 5, 1977 |title=WNEW Gets Madison Square Garden Award |magazine= Cash Box |location= USA|publisher=George Albert |volume=XXXIX |number=25|page=16|url=https://www.americanradiohistory.com/Archive-Cash-Box/70s/1977/CB-1977-11-05.pdf|via=americanradiohistory.com|access-date=March 30, 2019}}</ref> Because the arena has a seating capacity of about 20,000,<ref name="MSG SeatGeek">{{cite web|url=https://seatgeek.com/tba/articles/the-ultimate-guide-to-madison-square-garden/|title=The Ultimate Guide to Madison Square Garden|last=Bunt|first=Angela|date=April 30, 2018|website=SeatGeek|access-date=March 29, 2019|archive-url=https://web.archive.org/web/20190330015723/https://seatgeek.com/tba/articles/the-ultimate-guide-to-madison-square-garden/|archive-date=March 30, 2019|url-status=live}}</ref> this would require a minimum of five sold-out shows there. Chicago was one of at least eleven other acts that were eligible for the award,<ref name="BB Oct29_1977"/> and weeks later, at its October 28, 1977, Madison Square Garden concert,<ref>{{Cite news|url=https://www.nytimes.com/1977/10/29/archives/chicago-a-supremely-confident-rock-band.html|title=Chicago a Supremely Confident Rock Band|last=Palmer|first=Robert|date=October 29, 1977|work=The New York Times|access-date=March 29, 2019|language=en-US|issn=0362-4331|archive-url=https://web.archive.org/web/20190329212203/https://www.nytimes.com/1977/10/29/archives/chicago-a-supremely-confident-rock-band.html|archive-date=March 29, 2019|url-status=live}}</ref> Chicago was one of the first acts to receive the award for drawing over 180,000 people to the venue in nine sold-out appearances there over the years.<ref name= "MSG Gold Ticket Byrom">{{cite news |last=Byrom |first=Sue |title=The Current Scene: Chicago's Golden Ticket to Ride |newspaper=Scrantonian |location=Scranton, Pennsylvania, USA |date=February 5, 1978 |page=20 |url=https://www.newspapers.com/clip/30088798/the_scrantonian/ |via=[[Newspapers.com]] |access-date=March 30, 2019 |archive-url=https://web.archive.org/web/20190330221341/https://www.newspapers.com/clip/30088798/the_scrantonian/ |archive-date=March 30, 2019 |url-status=live  }}{{free access}}</ref><ref name="Cash Box Nov12_77">{{cite magazine |date=November 12, 1977 |title=New York Hosts Chicago |magazine= Cash Box |location= USA|publisher=George Albert |volume=XXXIX |number=26|pages=38|url=https://www.americanradiohistory.com/Archive-Cash-Box/70s/1977/CB-1977-11-12.pdf#page=38|via=americanradiohistory.com}}</ref> [[Cashbox (magazine)|''Cashbox'']] reviewer Ken Terry said of the 1977 Madison Square Garden concert, "Chicago ultimately presents itself in the best light with AM-oriented, good-time music. Its fans are not looking for complicated, introverted songs; they want music to drive to, dance to and work to."<ref name="Terry Nov12_77">{{cite magazine |last=Terry|first=Ken|date=November 12, 1977 |title=Talent: Chicago |magazine= Cash Box |location= USA|publisher=George Albert |volume=XXXIX |number=26|page=54|url=https://www.americanradiohistory.com/Archive-Cash-Box/70s/1977/CB-1977-11-12.pdf#page=54|via=americanradiohistory.com}}</ref>

Besides recording and touring, during the busy 1970s, Chicago also made time for a movie appearance and several television appearances of note. In 1972, Guercio produced and directed ''[[Electra Glide in Blue]]'', a film about an [[Arizona]] motorcycle policeman. Released in 1973, the film stars [[Robert Blake (actor)|Robert Blake]] and features Cetera, Kath, Loughnane, and Parazaider in supporting roles.<ref name="afi.com">{{Cite web|url=http://www.afi.com/members/catalog/DetailView.aspx?s=&Movie=54789|title=Detail view of Movies Page: Electra Glide in Blue|publisher=afi.com|access-date=January 16, 2017|archive-url=https://web.archive.org/web/20161013063656/http://www.afi.com/members//catalog/DetailView.aspx?s=&Movie=54789|archive-date=October 13, 2016|url-status=live}}</ref> The group also appears prominently on the film's [[movie soundtrack|soundtrack]]. Chicago made its "television variety debut" in February 1973 when they were the only rock musicians invited to appear on a television special honoring [[Duke Ellington]], ''Duke Ellington... We Love You Madly'', which aired on [[CBS]]. They performed the Ellington composition, "Jump for Joy".<ref name="Billboard 85 2 p16">{{cite magazine|date=January 13, 1973|title=From The Music Capitals of the World: New York|magazine=Billboard|location=New York, NY|publisher=Billboard Publications, Inc.|volume=85|number=2|url=https://books.google.com/books?id=MwkEAAAAMBAJ&pg=PA16|page=16|via=Google Books|access-date=October 15, 2017|archive-date=February 26, 2023|archive-url=https://web.archive.org/web/20230226055454/https://books.google.com/books?id=MwkEAAAAMBAJ&pg=PA16|url-status=live}}</ref><ref>{{cite news|last=Zonkel|first=Phillip|title=Hard habit to break: The men of Chicago just can't stop making new music|newspaper=Lancaster Eagle-Gazette|location=Lancaster, Ohio, USA|date=September 18, 1995|page=5, "CoverSTORY" section|url=https://www.newspapers.com/clip/15020655/lancaster_eaglegazette/|via=[[Newspapers.com]]|access-date=November 10, 2017|archive-url=https://web.archive.org/web/20171111041813/https://www.newspapers.com/clip/15020655/lancaster_eaglegazette/|archive-date=November 11, 2017|url-status=live}}{{free access}}</ref><ref name="Billboard 85 6 p17">{{cite magazine|date=February 10, 1973|title=Duke Ellington ...We Love You Madly|magazine=Billboard|location=New York, NY|publisher=Billboard Publications, Inc.|volume=85|number=6|url=https://books.google.com/books?id=NgkEAAAAMBAJ&pg=PA17|page=17|via=Google Books|access-date=October 15, 2017|archive-date=February 26, 2023|archive-url=https://web.archive.org/web/20230226055454/https://books.google.com/books?id=NgkEAAAAMBAJ&pg=PA17|url-status=live}}</ref> In July 1973, the group starred in a half-hour television special produced by [[Dick Clark]], ''Chicago in the Rockies'', which aired in [[prime time]] on [[American Broadcasting Company|ABC]]. The show was filmed on location at [[Caribou Ranch]], the 3,000-acre ranch-turned-recording studio located outside of [[Boulder, Colorado]], owned by Chicago's producer, James William Guercio. The only musical guest on the show was [[Al Green]], who was rated the number-one male vocalist of 1972, and whom ''[[Rolling Stone]]'' magazine named "Rock and Roll Star of the Year".<ref name="Martin 1973">{{cite news |last=Martin |first=Bob |title=Al Green on rock special |newspaper=Independent |location=Long Beach, California, USA |date=July 17, 1973 |page=C20 |url=https://www.newspapers.com/clip/14426501/independent/ |via=[[Newspapers.com]] |access-date=October 15, 2017 |archive-url=https://web.archive.org/web/20171016014935/https://www.newspapers.com/clip/14426501/independent/ |archive-date=October 16, 2017 |url-status=live  }}{{free access}}</ref> That special was followed by a second hour-long special the next year, ''Chicago ... Meanwhile, Back at the Ranch'', which aired in prime time on ABC in August 1974. ''Chicago ... Meanwhile, Back at the Ranch'' was again shot on location at Caribou Ranch and was again produced by Dick Clark. Singer [[Anne Murray]] and country music star [[Charlie Rich]] were guests on the show.<ref name="Corsicana 1974">{{cite news |title='Chicago' Special Recreates Silent Flicks With Music |newspaper=Corsicana Daily Sun |location=Corsicana, Texas, USA |date=August 11, 1974 |page=16 (television listing supplement) |url=https://www.newspapers.com/clip/14427042/corsicana_daily_sun/ |via=[[Newspapers.com]] |access-date=October 15, 2017 |archive-url=https://web.archive.org/web/20171016014341/https://www.newspapers.com/clip/14427042/corsicana_daily_sun/ |archive-date=October 16, 2017 |url-status=live  }}{{free access}}</ref> Clark produced a third television special starring Chicago, ''[[Dick Clark's New Year's Rockin' Eve|Chicago's New Year's Rockin' Eve 1975]]'', which aired on ABC on December 31, 1974. Musical guests on the {{frac|1|1|2}}-hour-long show included [[the Beach Boys]], [[the Doobie Brothers]], [[Olivia Newton-John]], and [[Herbie Hancock]]. It was the third ''Rockin' Eve'' Clark had produced, and it competed with [[Guy Lombardo]]'s traditional [[New Year's Eve]] television show which aired on a different network and was in its 45th consecutive year of broadcast. Clark hoped the ''Rockin' Eve'' format would become an "annual TV custom".<ref name="Clark v Lombardo new year">{{cite news|last=Harris|first=Harry|title=It's Clark Vs. Lombardo at Midnight|newspaper=The Philadelphia Inquirer|location=Philadelphia, Pennsylvania, USA|date=December 31, 1974|page=3-C|url=https://www.newspapers.com/clip/15069750/the_philadelphia_inquirer/|via=[[Newspapers.com]]|access-date=November 12, 2017|archive-url=https://web.archive.org/web/20171113060252/https://www.newspapers.com/clip/15069750/the_philadelphia_inquirer/|archive-date=November 13, 2017|url-status=live}}{{free access}}</ref>

==== Death of Terry Kath and transition ====
The year 1978 began with a split with Guercio.<ref name= Ruhlmannp7 /> Chicago had recorded its last five studio albums ''Chicago VI'', ''VII'', ''VIII'', ''X'', and ''XI,''<ref name="Ruhlmannp6">{{cite AV media notes|title=Chicago Group Portrait (Box Set)|year=1991|url=http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_6.html|page=6|access-date=October 15, 2016|first=William James|last=Ruhlmann|format=CD booklet archived online|publisher=Columbia Records|location=New York City, NY|quote=the sixth, seventh, eighth, tenth and eleventh albums were done up at Caribou Ranch|archive-url=https://web.archive.org/web/20160313205646/http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_6.html|archive-date=March 13, 2016|url-status=live}}</ref> and had made two television specials at Guercio's Caribou Ranch. In later years, band members cited Guercio's purchase of Caribou Ranch, more particularly their realization that Guercio had enough money to purchase Caribou Ranch, as a contributing factor to their disillusionment with him as a producer. They felt he had taken advantage of them financially.<ref name="Seraphine" />{{rp|131}}<ref>{{cite AV media | people=Pardini, Peter (Director) |year=2016 | title=Now More Than Ever: The History of Chicago |medium=Documentary film |time=Part VII: I'd Rather Be Rich | location=USA | publisher=Chicago }}</ref> Then on January 23 of that same year, Kath died of an accidental, self-inflicted gunshot wound from a gun he thought was unloaded.<ref name= Ruhlmannp8>{{cite AV media notes|title=Chicago Group Portrait (Box Set)|year=1991|url=http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_8.html|page=8|access-date=February 9, 2017|first=William James|last=Ruhlmann|format=CD booklet archived online|publisher=Columbia Records|location=New York City, NY|archive-url=https://web.archive.org/web/20120116085147/http://aln3.albumlinernotes.com/Chicago_Box_Set_-_Page_8.html|archive-date=January 16, 2012|url-status=live}}</ref><ref>{{cite web|url=http://ultimateclassicrock.com/terry-kath-strange-rock-deaths/|title=Terry Kath--Accidentally Shot Himself|date=November 2, 2012 |publisher=Ultimateclassicrock.com|access-date=December 18, 2015|archive-url=https://web.archive.org/web/20151222161230/http://ultimateclassicrock.com/terry-kath-strange-rock-deaths/|archive-date=December 22, 2015|url-status=live}}</ref> [[Doc Severinsen]], who was the bandleader for ''[[The Tonight Show Starring Johnny Carson]]'' at the time and a friend of the group, visited them after Kath's funeral and encouraged them to continue. According to writer Jim Jerome, the visit "snapped them back" and helped them make the decision to carry on.<ref name=People1978>Jerome, Jim (October 16, 1978). [http://www.people.com/people/archive/article/0,,20071963,00.html "Chicago's 'Alive Again{{'"}}] {{Webarchive|url=https://web.archive.org/web/20160427222113/http://www.people.com/people/archive/article/0,,20071963,00.html |date=April 27, 2016}}. ''[[People Weekly]]''. Retrieved February 9, 2017.</ref>

After auditioning over 30 potential replacements for Kath, Chicago decided upon guitarist and singer-songwriter [[Donnie Dacus]].<ref name=People1978 /><ref name= Ruhlmannp8 /> While filming for the musical ''[[Hair (movie)|Hair]]'', he joined the band in April 1978 just in time to record the ''[[Hot Streets]]'' album.<ref name=People1978 /> Its energetic lead-off single, "[[Alive Again (Chicago song)|Alive Again]]", brought Chicago back to the Top 15;<ref name=BBChicagoHot100 /> Pankow wrote it "originally as a love song but ultimately as recognition of Kath's guiding spirit shining down from above".<ref>{{Cite AV media notes |title=The Box |title-link=The Box (Chicago album) |author=Chicago |year=2003 |publisher=[[Rhino Entertainment|Rhino Records]]}}</ref>

The 1978 album ''Hot Streets'' was produced by [[Phil Ramone]].<ref name=People1978 /><ref name= Ruhlmannp8 /> It was Chicago's first album with a title rather than a number; and was the band's first LP to have a picture of the band (shot by photographer [[Norman Seeff]])<ref>{{cite AV media notes|title= Hot Streets|year= 1978|url= http://aln2.albumlinernotes.com/Hot_Streets.html|access-date= February 9, 2017|format= album liner notes archived online|publisher= Columbia Records|location= New York City, NY|archive-url= https://web.archive.org/web/20170211080602/http://aln2.albumlinernotes.com/Hot_Streets.html|archive-date= February 11, 2017|url-status=live|df= mdy-all}}</ref> featured prominently on the cover (with the ubiquitous logo downsized).<ref name=People1978 /><ref name= Ruhlmannp8 /> These two moves were seen by many as indications that the band had changed following Kath's death.<ref name=People1978 /> To a degree, the band returned to the old naming scheme on its subsequent releases, although most titles now bore [[Arabic numerals]] rather than Roman numerals. ''Hot Streets'', the band's 12th album, peaked at No. 12 on the [[Billboard charts|''Billboard'' charts]];<ref name= "Chicago Billboard 200" /> it was Chicago's first release since their debut to fail to make the Top 10. According to Jeff Giles, "Although Chicago quickly soldiered on [after Kath's death], releasing their ''Hot Streets'' album with new guitarist Donnie Dacus that October, it was impossible not to notice the loss of momentum."<ref name=":10" /> The release also marked a move somewhat away from the jazz-rock direction favored by Kath and towards more pop songs and ballads. Dacus stayed with the band through the 1979 album ''[[Chicago 13]]'',<ref name= Ruhlmannp8 /> and is also featured in a promotional video on the DVD included in the [[Rhino Records]] Chicago box set from 2003. Again produced by Ramone, it was the group's first studio album not to contain a Top 40 hit. Dacus departed from the band following the conclusion of the concert tour in support of ''Chicago 13'', in 1980.<ref name="Sweet home Chicago">{{Cite news|url=http://www.cleburnetimesreview.com/news/sweet-home-chicago/article_4eb8638c-f2d4-11e5-b4d6-fb882c3cae3a.html|title=Sweet home Chicago|last=Smith|first=Matt|date=March 26, 2016|work=[[Cleburne Times-Review]]|access-date=July 15, 2018|publisher=Kay Helms|location=Cleburne, Texas, U.S.A.|language=en|archive-url=https://web.archive.org/web/20181116050138/https://www.cleburnetimesreview.com/news/sweet-home-chicago/article_4eb8638c-f2d4-11e5-b4d6-fb882c3cae3a.html|archive-date=November 16, 2018|url-status=live}}</ref>

=== 1980s: changing sound ===
''[[Chicago XIV]]'' (1980), produced by [[Tom Dowd]], relegated the horn section to the background on a number of tracks, and the album's two singles failed to make the Top 40. [[Chris Pinnick]] joined the band to play guitar and remained through 1985,<ref name= Ruhlmannp8 /> and the band were also augmented by saxophone player [[Marty Grebb]] on the subsequent tour.<ref name= "Koshatka Sept1980">{{cite news |last=Koshatka |first=Edgar |title=Chicago's welcome comeback |newspaper=[[The Philadelphia Inquirer]] |location=Philadelphia, Pennsylvania, USA |date=September 21, 1980 |page=8-I |url=https://www.newspapers.com/clip/13993607/the_philadelphia_inquirer/ |via=[[Newspapers.com]] |access-date=September 25, 2017 |archive-url=https://web.archive.org/web/20170925225943/https://www.newspapers.com/clip/13993607/the_philadelphia_inquirer/ |archive-date=September 25, 2017 |url-status=live  }} {{free access}}</ref> Marty Grebb had formerly been with [[the Buckinghams]], and before that had been Cetera's bandmate in a local Chicago area cover band called the Exceptions.<ref>{{Cite news|url=http://forbassplayersonly.com/bob-lizik/|title=Bob Lizik: Exclusive interview with FBPO's Jon Liebman|last=Liebman|first=Jon|date=July 10, 2017|work=For Bass Players Only|access-date=October 24, 2017|language=en-US|archive-url=https://web.archive.org/web/20171024205612/http://forbassplayersonly.com/bob-lizik/|archive-date=October 24, 2017|url-status=live}}</ref> The album peaked at No. 71 on the ''Billboard'' 200,<ref name= "Chicago Billboard 200" /> and failed to reach gold certification by the RIAA.<ref name="Gold & Platinum by Artist" /> Believing the band to no longer be commercially viable, Columbia Records dropped them from its roster in 1981 and released a [[Greatest Hits, Volume II (Chicago album)|second greatest hits volume]] (counted as ''Chicago XV'' in the album chronology) later that year to fulfill its contractual obligation.<ref name=Ruhlmannp8/>

In late 1981, the band had new management, a new producer ([[David Foster]]),<ref name= Ruhlmannp8 /> a new label ([[Warner Bros. Records]]),<ref name= Ruhlmannp8 /> and the addition of keyboardist, guitarist, and singer [[Bill Champlin]] ([[Sons of Champlin]]).<ref name="Van Matre June1982">{{cite news |last=Van Matre |first=Lynn |title=Revitalized Chicago back on road again |newspaper=[[Chicago Tribune]] |location=Chicago, Illinois, USA |date=June 13, 1982 |page=5 (Section 6) |url=http://archives.chicagotribune.com/1982/06/13/page/151/article/rock |access-date=September 26, 2017 |archive-url=https://web.archive.org/web/20170117065009/http://archives.chicagotribune.com/1982/06/13/page/151/article/rock/ |archive-date=January 17, 2017 |url-status=live  }}</ref> Percussionist Laudir de Oliveira and Marty Grebb departed from the band. During Foster's stewardship, less of an emphasis was placed on the band's horn-based sound, being replaced by lush [[Ballad|power ballads]], which became Chicago's style during the 1980s. The new sound brought more singles success to the band.

For the 1982 album ''[[Chicago 16]]'', the band worked with composers from outside the group for the first time, and Foster brought in studio musicians for some tracks (including the core members of [[Toto (band)|Toto]]),<ref name="Van Matre June1982"/> and used new technology (such as synthesizers) to "update" and streamline the sound, further pushing back the horn section, and in some cases not even using them at all. The band did return to the charts with the Cetera-sung ballad "[[Hard to Say I'm Sorry|Hard to Say I'm Sorry/Get Away]]", which is featured in the soundtrack of the [[Daryl Hannah]] film ''[[Summer Lovers]]''.<ref>{{Cite web|url=http://www.afi.com/members/catalog/DetailView.aspx?s=&Movie=56885|title=AFI Catalog of Feature Films: Summer Lovers|website=afi.com|publisher=American Film Institute|access-date=September 25, 2017|archive-url=https://web.archive.org/web/20170709051849/http://www.afi.com/members//catalog/DetailView.aspx?s=&Movie=56885|archive-date=July 9, 2017|url-status=live}}</ref> Co-written by Cetera and David Foster, "Hard to Say I'm Sorry" was the group's second single to reach No. 1 on the Hot 100 chart<ref name=BBChicagoHot100 /> and gave them a nomination for the [[Grammy Award for Best Pop Performance by a Duo or Group with Vocals|Grammy Award for Best Pop Performance by a Duo or Group with Vocal]].<ref name="grammy awards Chicago" /> ''Chicago 16'' reached both gold and platinum status during the year of its release,<ref name="Gold & Platinum by Artist" /> and went to No. 9 on the ''Billboard'' 200 album chart.<ref name= "Chicago Billboard 200" />

1984's ''[[Chicago 17]]'' became the biggest selling album in the band's history, certified by the RIAA in 1997 as six times multi-platinum.<ref>{{Cite news|url=https://www.riaa.com/gold-platinum/?tab_active=awards_by_artist#search_section|title=Gold & Platinum - RIAA by Artists|work=RIAA|access-date=September 25, 2017|language=en-US|archive-url=https://web.archive.org/web/20161216204505/http://www.riaa.com/gold-platinum/?tab_active=awards_by_artist#search_section|archive-date=December 16, 2016|url-status=live}}</ref> The album produced two more Top Ten (both No. 3) singles,<ref>{{Cite magazine|url=https://www.billboard.com/articles/columns/chart-beat/959544/ask-billboard-taking-peaks-nos-100-1|title=Ask Billboard: "Taking Peaks", Nos. 100-1|last=Trust|first=Gary|date=January 29, 2010|magazine=Billboard|access-date=September 25, 2017|archive-url=https://web.archive.org/web/20171125141030/https://www.billboard.com/articles/columns/chart-beat/959544/ask-billboard-taking-peaks-nos-100-1|archive-date=November 25, 2017|url-status=live}}</ref> "[[You're the Inspiration]]", written by Cetera and David Foster, and "[[Hard Habit to Break]]", written by&nbsp;[[Steve Kipner]]&nbsp;and John Lewis Parker. The single, "Hard Habit to Break", brought two more Grammy Award nominations for the band, for [[Grammy Award for Record of the Year|Record of the Year]] and [[Grammy Award for Best Pop Performance by a Duo or Group with Vocals|Best Pop Performance by a Duo or Group with Vocals]].<ref name="grammy awards Chicago" /> The album included two other singles: "[[Stay the Night (Chicago song)|Stay the Night]]" (No. 16),<ref name=BBChicagoHot100 /> another composition by Cetera and Foster; and "[[Along Comes a Woman]]" (No. 14),<ref name=BBChicagoHot100 /> written by Cetera and Mark Goldenberg. Peter's brother, Kenny Cetera, who had provided background vocals on the ''Chicago 17'' album,<ref name="17 LP liner notes">{{cite AV media notes |title=Chicago 17 |author=Chicago |year=1984 |type=vinyl LP liner |publisher=[[Warner Bros. Records|Warner Bros. Records Inc.]] |id=9 25060-1}}</ref> was brought into the group for the ''17'' tour to add percussion and high harmony vocals.<ref name=Metella>{{cite news |last=Metella |first=Helen |title=Chicago puts on a classy show |newspaper=The Edmonton Journal |date=April 10, 1985 |page=C5 |location=Edmonton, Alberta, Canada |url=https://www.newspapers.com/clip/29934402/edmonton_journal/ |via=[[Newspapers.com]] |access-date=March 26, 2019 |url-status=live  |archive-url=https://web.archive.org/web/20190327093520/https://www.newspapers.com/clip/29934402/edmonton_journal/ |archive-date=March 27, 2019 }} {{free access}}</ref><ref name="Bahr Oct1984">{{cite news |last=Bahr |first=Jeff |title=Chicago hits musical homer |newspaper=The Lincoln Star |date=October 6, 1984 |page=5 |location=Lincoln, Nebraska, USA |url=https://www.newspapers.com/clip/13980897/the_lincoln_star/ |via=[[Newspapers.com]] |access-date=September 24, 2017 |archive-url=https://web.archive.org/web/20170925083451/https://www.newspapers.com/clip/13980897/the_lincoln_star/ |archive-date=September 25, 2017 |url-status=live  }} {{free access}}</ref>

By 1985, the band was embracing the newest medium, the music video channel [[MTV]], by releasing music videos for four songs. They featured a track titled "Good for Nothing" on the 1985 global activist album, ''[[We Are the World (album)|We Are the World]]''.<ref name="We Are the World, at AllMusic">{{allMusic | class=album | id=mw0000196167 | label=USA for Africa: We Are the World | access-date=May 27, 2013 }}</ref> As contributors to the album, along with all other artists who were on the album, the band received its last nomination for a Grammy Award, for [[Grammy Award for Album of the Year|Album of the Year]].<ref name="grammy awards Chicago" />

At the [[American Music Awards of 1986|13th Annual American Music Awards]], held January 27, 1986, Chicago won the award for [[American Music Award for Favorite Pop/Rock Band/Duo/Group|Favorite Pop/Rock Band/Duo/Group]] for the second time.<ref name="AMA Winner Database" /> It is the last American Music Award the band has received.

==== Peter Cetera departure and continued success ====
Concurrently with Chicago's existing career, vocalist Peter Cetera had begun a solo career. He proposed an arrangement with the band where they would take hiatuses after tours to let him focus on solo work (mirroring that of [[Phil Collins]] and [[Genesis (band)|Genesis]]), but the band declined. Cetera ultimately left Chicago in the summer of 1985.<ref name="People 1987">{{cite magazine|url=https://www.people.com/people/archive/article/0,,20095555,00.html |title=Glory of Love Singer Peter Cetera Left Chicago (the Band) for Idaho (the State) and Solo Success |last1=Dougherty |first1=Steve |first2=Todd|last2=Gold|date=February 2, 1987|magazine=[[People (magazine)|People]]|pages=60–62|access-date=March 20, 2010 |language=en-US |archive-url=https://web.archive.org/web/20121008230909/http://www.people.com/people/archive/article/0,,20095555,00.html |archive-date=October 8, 2012 |url-status=live }}</ref><ref>{{Cite web |title=August 1986: Peter Cetera Cracks No. 1 with "Glory of Love" |url=https://weareclassicrockers.com/article/august-1986-peter-cetera-cracks-no-1-glory-love |access-date=April 14, 2023 |website=Weareclassicrockers |language=en-US  |archive-date=April 14, 2023 |archive-url=https://web.archive.org/web/20230414191928/https://weareclassicrockers.com/article/august-1986-peter-cetera-cracks-no-1-glory-love |url-status=live }}</ref> He soon topped the charts with "[[Glory of Love (Peter Cetera song)|Glory of Love]]" (the theme song of the film ''[[The Karate Kid Part II]]''), and with "[[The Next Time I Fall]]" (a duet with [[Amy Grant]]). Two more songs reached the top ten: a 1988 solo hit called "[[One Good Woman]]" (No. 4 U.S.), and a 1989 duet with [[Cher]] called "[[After All (Cher and Peter Cetera song)|After All]]" (No. 6 U.S.). In 1992, Cetera released his fourth studio album, ''[[World Falling Down]]'', which earned him three hits on the Adult Contemporary charts, including the single "Restless Heart". Cetera's former position was filled by bassist and singer-songwriter [[Jason Scheff]], son of [[Elvis Presley]]'s bassist [[Jerry Scheff]].<ref name="Duffy Mar1987">{{Cite news|url=https://www.orlandosentinel.com/1987/03/08/scheffs-chicago-habit-is-still-hard-to-break/|title=Scheff's Chicago Habit Is Still Hard To Break|last=Duffy|first=Thom|date=March 8, 1987|work=tribunedigital-orlandosentinel|access-date=August 25, 2017|language=en|archive-url=https://web.archive.org/web/20170825191318/http://articles.orlandosentinel.com/1987-03-08/entertainment/0110330284_1_jason-scheff-jerry-scheff-peter-cetera|archive-date=August 25, 2017|url-status=live}}</ref> Guitarist Chris Pinnick also left the group in 1985, prior to the recording of the band's next album.<ref>{{Cite web |last=Moehlis |first=Jeff |date=July 9, 2014 |title=Jeff Moehlis: Playing in the Pocket — Guitarist Chris Pinnick Talks About Upcoming Show |url=http://www.noozhawk.com/jeff_moehlis_interview_with_chris_pinnick_of_pockets/ |access-date=April 14, 2023 |website=Noozhawk |language=en-US |archive-date=April 18, 2023 |archive-url=https://web.archive.org/web/20230418214403/https://www.noozhawk.com/jeff_moehlis_interview_with_chris_pinnick_of_pockets/ |url-status=live }}</ref>

For the final Foster-produced album, ''[[Chicago 18]]'', the band filled Pinnick's spot with several session guitarists, none of whom became band members. The album was released on September 29, 1986,<ref>{{Cite web|url=https://www.chicagotheband.com/albums/chicago18.html|title=Chicago 18|website=chicagotheband.com|archive-url=https://web.archive.org/web/20170113010334/http://www.chicagotheband.com/albums/chicago18.html|archive-date=January 13, 2017|url-status=dead|access-date=October 2, 2017}}</ref> and included the No. 3 single "[[Will You Still Love Me? (song)|Will You Still Love Me?]]", and top 20 single "[[If She Would Have Been Faithful...]]", in addition to an updated version of "[[25 or 6 to 4]]" with a video that got airplay on MTV. The video won an award for Best Cinematography for Bobby Byrne at the [[American Video Awards]].<ref name="Sledgehammer wins" /> Soon after the album was recorded, the band hired guitarist [[Dawayne Bailey]],<ref name="Bishop Oct1986">{{cite news |last=Bishop |first=Pete |title=Chicago brings out old talents, new hits, but fewer fans |newspaper=The Pittsburgh Press |location=Pittsburgh, Pennsylvania, USA |date=October 22, 1986 |page=C8 |url=https://www.newspapers.com/clip/13996495/the_pittsburgh_press/ |via=[[Newspapers.com]] |access-date=September 25, 2017 |archive-url=https://web.archive.org/web/20170926041931/https://www.newspapers.com/clip/13996495/the_pittsburgh_press/ |archive-date=September 26, 2017 |url-status=live  }} {{free access}}</ref><ref>{{cite news |last=Heckman |first=Don |title=Chicago Resounds with More Voice, Less Horn |newspaper=Los Angeles Times |location=Los Angeles, California, USA |date=November 27, 1986 |page=VI-8 |url=https://www.newspapers.com/clip/13996249/the_los_angeles_times/ |via=[[Newspapers.com]] |access-date=September 25, 2017 |archive-url=https://web.archive.org/web/20170926041200/https://www.newspapers.com/clip/13996249/the_los_angeles_times/ |archive-date=September 26, 2017 |url-status=live  }} {{free access}}</ref> formerly of [[Bob Seger]]'s Silver Bullet Band.<ref>{{cite news |last=Graff |first=Gary |title=Chicago is faithful to its past and ready to move on |newspaper=The Morning Call |agency=KNT News Wire |location=Allentown, Pennsylvania, USA |date=September 5, 1987 |pages=A52, A56 |url=https://www.newspapers.com/clip/13997068/the_morning_call/ |via=[[Newspapers.com]] |access-date=September 25, 2017 |archive-url=https://web.archive.org/web/20170926095621/https://www.newspapers.com/clip/13997068/the_morning_call/ |archive-date=September 26, 2017 |url-status=live  }} {{free access}}</ref> Bailey and Scheff had previously played in bands together, so Scheff introduced Bailey to the band in time for the ''Chicago 18'' tour.

For the 1988 release ''[[Chicago 19]]'', the band had replaced producer Foster with co-producers [[Ron Nevison]], who had recently produced two albums for [[Heart (band)|Heart]], and Chas Sanford, who had worked with [[Rod Stewart]] and [[Stevie Nicks]].<ref>{{cite news |last=Kiss |first=Tony |title=Chicago Keeps Hits Coming After 20 Years |newspaper=Asheville Citizen-Times |location=Asheville, North Carolina, USA |date=September 4, 1988 |page=1L |url=https://www.newspapers.com/clip/14017656/asheville_citizentimes/ |via=[[Newspapers.com]] |access-date=September 26, 2017 |archive-url=https://web.archive.org/web/20170927052219/https://www.newspapers.com/clip/14017656/asheville_citizentimes/ |archive-date=September 27, 2017 |url-status=live  }} {{free access}}</ref> They topped the charts again with the [[Diane Warren]]-composed single "[[Look Away]]". It was the third and last Chicago single to reach No. 1 on the Hot 100 chart.<ref name= BBChicagoHot100 /> The song ultimately was named as the "''Billboard'' Hot 100 No. 1 Song of the Year" for 1989.<ref>{{Cite magazine|url=https://billboard.com/photos/6803735/billboard-hot-100-no-1-songs-of-the-year-1958-2015|title=Billboard Hot 100 No. 1 Songs of the Year: 1958-2015|date=December 10, 2015|magazine=Billboard|access-date=September 25, 2017|archive-url=https://web.archive.org/web/20171024145346/http://www.billboard.com/photos/6803735/billboard-hot-100-no-1-songs-of-the-year-1958-2015 |archive-date=October 24, 2017 |url-status=live  }}</ref> The album also yielded two more top 10 hits, "[[I Don't Wanna Live Without Your Love]]" and "[[You're Not Alone (Chicago song)|You're Not Alone]]",<ref name= BBChicagoHot100 /> both with Champlin singing lead vocals, and the Scheff-sung No. 55 single, "We Can Last Forever", in addition to including the original version of a top 5 single titled "[[What Kind of Man Would I Be?]]". The latter, also sung by Scheff, was remixed for inclusion on the band's forthcoming greatest hits record (and 20th album), ''[[Greatest Hits 1982–1989]]'', and it was this version that became a hit.

=== 1990s: more changes and ''Stone of Sisyphus'' ===
{{Main|Chicago XXXII: Stone of Sisyphus{{!}}''Chicago XXXII: Stone of Sisyphus''}}
The beginning of the 1990s brought yet another departure. Original drummer Danny Seraphine was dismissed from the band in May 1990.<ref name="RRHOF Bio">{{Cite web|url=https://www.rockhall.com/inductees/chicago|title=Chicago: Biography|last=Bowman|first=Rob|website=Rock & Roll Hall of Fame|language=en-US|access-date=September 27, 2017|archive-url=https://web.archive.org/web/20170116154323/https://www.rockhall.com/inductees/chicago|archive-date=January 16, 2017|url-status=live}}</ref> Seraphine was succeeded by [[Tris Imboden]],<ref name="RRHOF Bio" /> a longtime drummer with [[Kenny Loggins]]<ref>{{Cite news|url=http://www.malibusurfsidenews.com/tris-imboden-finds-peace-quiet-malibu|title=Tris Imboden finds peace, quiet in Malibu|last=Burke|first=Barbara|date=February 10, 2017|work=Malibu Surfside News|publisher=22nd Century Media, LLC|access-date=September 27, 2017|language=en-US|archive-url=https://web.archive.org/web/20170928055913/http://www.malibusurfsidenews.com/tris-imboden-finds-peace-quiet-malibu|archive-date=September 28, 2017|url-status=usurped}}</ref> and former session drummer with [[Peter Cetera]].<ref>{{cite AV media notes |title=[[One More Story]] |author=[[Peter Cetera]] |year=1988 |type=CD booklet |page=13 |publisher=[[Warner Bros. Records|Warner Bros. Records Inc.]] |id=9 25704-2}}</ref> Imboden made his first appearance on the 1991 album ''[[Twenty 1]]'' with a fragment of band's logo, which yielded an eleven-week stretch on the ''Billboard'' 200, a peak at No. 66,<ref name="Billboard 200: 1991: Chicago">{{cite magazine|magazine=Billboard|title=Chicago – Chart history|url=https://www.billboard.com/artist/chicago/chart-history/billboard-200|access-date=June 8, 2013|archive-date=November 21, 2021|archive-url=https://web.archive.org/web/20211121090925/https://www.billboard.com/artist/chicago/chart-history/billboard-200/|url-status=live}}</ref> and the song "Chasin' the Wind" which peaked at No. 39. ''Twenty 1'' would be their last released album of original music for fifteen years.

The band was recognized with a star on the [[Hollywood Walk of Fame]] on July 23, 1992.<ref name="walkoffame1">{{cite web|url=http://www.walkoffame.com/chicago|title=Chicago|publisher=Walkoffame.com|access-date=April 10, 2016|archive-url=https://web.archive.org/web/20160403074208/http://walkoffame.com/chicago|archive-date=April 3, 2016|url-status=live|language=en-US}}</ref>

In 1993, Chicago wrote and recorded their 22nd album ''[[Chicago XXXII: Stone of Sisyphus|Stone of Sisyphus]]''.<ref name="Payne June2008">{{Cite web|url=http://www.cnn.com/2008/SHOWBIZ/Music/06/17/chicago.album/|title=Chicago releases 'lost' album 15 years after recording it|last=Payne|first=Ed|date=June 17, 2008|publisher=CNN|language=en-US|access-date=September 29, 2017|archive-url=https://web.archive.org/web/20170929183541/http://www.cnn.com/2008/SHOWBIZ/Music/06/17/chicago.album/|archive-date=September 29, 2017|url-status=live}}</ref> This album was to have marked their return to their traditional composition of the 1970s, emphasizing major horn accompaniment.<ref name="LeRoy July2008">{{Cite web|url=https://www.clevescene.com/cleveland/chicago-returns-with-a-record-that146s-been-sitting-on-the-shelves-for-15-years/Content?oid=1506439|title=Chicago returns with a record that's been sitting on the shelves for 15 years|last=LeRoy|first=Dan|date=July 2, 2008|website=Cleveland Scene|location=Cleveland, Ohio, USA|access-date=September 29, 2017|archive-url=https://web.archive.org/web/20170929183116/https://www.clevescene.com/cleveland/chicago-returns-with-a-record-that146s-been-sitting-on-the-shelves-for-15-years/Content?oid=1506439|archive-date=September 29, 2017|url-status=live|language=en-US}}</ref> However, following a reorganization of the record company, the new executives at [[Reprise Records]] (now part of the newly formed [[Warner Music Group]]) rejected the completed album. It remained unpublished for fifteen years, aside from [[bootleg recording|bootleg tapes]] and Internet files.<ref name="Payne June2008" /> This contributed to the parting of the band from the record label. The band was dismayed by the failure of the label. Upset with the shelving of the album, [[Dawayne Bailey]] voiced his objections and his annual contract was not renewed by the band in late 1994. And in the years that followed there were many debates and conjecture about the events surrounding the recordings. It was also suggested some years later that the band's management was negotiating with the label regarding a licensing of the extensive Chicago back catalog, and when those talks stalled, the label apparently retaliated by scrapping the project.<ref name="LeRoy July2008" /> The album eventually saw an expanded release on Rhino Records in June 2008, and made it to No. 122 on the album charts.<ref name= "Chicago Billboard 200" />

After finishing their 1994 tour, and after signing with the Warner Bros. Records imprint label [[Giant Records (Warner)|Giant Records]], they released their 1995 album ''[[Night & Day Big Band|Night & Day: Big Band]]'',<ref name=":5" /><ref name="Night & Day: Big Band, credits at AllMusic">{{allMusic | id=mw0000175235 | class=album | tab=credits | access-date=July 15, 2013 }}</ref> consisting of covers of songs originally recorded by [[Sarah Vaughan]], [[Glenn Miller]], and [[Duke Ellington]]. Guitarist [[Bruce Gaitsch]] stepped in and joined the band to handle the album's guitar work.<ref>{{Cite news|url=http://www.westcoast.dk/interviews/interviews-2007/robert-lamm-2007/|title=Robert Lamm - 2007|last=Lauridsen|first=Morten|date=November 2007|work=Blue Desert|access-date=December 4, 2017|archive-url=https://web.archive.org/web/20171205093018/http://www.westcoast.dk/interviews/interviews-2007/robert-lamm-2007/|archive-date=December 5, 2017|url-status=live|language=en-US}}</ref><ref>{{Cite AV media notes |title=[[Night & Day Big Band|Night & Day: Big Band]] |author=Chicago |year=1995 |page=2 |type=CD booklet |publisher=[[Giant Records (Warner)|Giant]] |id=24615-2 |location=Beverly Hills, California}}</ref><ref>{{Cite AV media notes |title=[[The Box (Chicago album)|The Box]] |author=Chicago |year=2003 |page=59 |type=CD booklet |publisher=[[Rhino Records]] |id=R2 73871 }}</ref> The album featured guest appearances by [[Paul Shaffer]] of ''[[Late Show with David Letterman]]'' fame, [[Aerosmith]] guitarist [[Joe Perry (musician)|Joe Perry]], and [[the Gipsy Kings]].<ref>{{Cite AV media notes |title=[[Night & Day Big Band|Night & Day: Big Band]] |author=Chicago |year=1995 |page=2 |type= CD booklet |publisher=[[Giant Records (Warner)|Giant]] |id=24615-2 |location=Beverly Hills, California}}</ref> Parazaider cited the group's participation in the 1973 television special honoring Duke Ellington, ''Duke Ellington... We Love You Madly'', as key in their decision to record this album.<ref>{{Cite web|url=https://www.chicagotheband.com/chicago_story.html|title=The Chicago Story: Chapter XII – The Next Duke Ellingtons|website=chicagotheband.com|archive-url=https://web.archive.org/web/20170102043938/http://www.chicagotheband.com/chicago_story.html|archive-date=January 2, 2017|url-status=dead|language=en-US|access-date=November 10, 2017}}</ref> After this big band album, Chicago acquired the rights to their Columbia recordings and reissued them on their own imprint.<ref name=":5" /> In early 1995, [[Keith Howland]], who had been a studio musician and stage hand based in Los Angeles, was recruited as Chicago's new permanent guitarist.<ref name=JMU>{{Cite web|url=http://www.jmu.edu/montpelier/issues/winter97/sound.html|title=Montpelier Winter 1997: Sound and Screen|last=Eisenberg|first=Sherri|date=Winter 1997|website=jmu.edu|publisher=James Madison University|access-date=September 28, 2017|archive-url=https://web.archive.org/web/20160828010124/http://www.jmu.edu/montpelier/issues/winter97/sound.html|archive-date=August 28, 2016|url-status=live|language=en-US}}</ref>

In 1998, Chicago released ''[[Chicago XXV: The Christmas Album]]'' and a live album in 1999, ''[[Chicago XXVI: Live in Concert|Chicago XXVI]]'' on their own imprint.<ref name=":5" />

=== 2000s ===
[[File:Chicagothebandmillbrook lar.jpg|left|thumb|Chicago in 2004 (l–r): Howland, Pankow, Champlin, Parazaider, Imboden, Loughnane, Scheff, and Lamm (behind Scheff)]]

In 2002, the band licensed their entire recorded output to [[Rhino Entertainment|Rhino Records]],<ref name=":5">{{Cite web |last=Gallo |first=Phil |date=May 6, 2002 |title=Rhino Records' kind of town |url=https://variety.com/2002/scene/markets-festivals/rhino-records-kind-of-town-1117866449/ |access-date=April 14, 2023 |website=Variety |archive-url=https://web.archive.org/web/20230414195606/https://variety.com/2002/scene/markets-festivals/rhino-records-kind-of-town-1117866449/ |archive-date=April 14, 2023 |url-status=live |language=en-US  }}</ref> after having recorded it at Columbia Records and Warner Bros. Records. In 2002, Rhino released a two-disc compilation, ''[[The Very Best of: Only the Beginning]]'', which spanned the band's career. The compilation made the [[Top 40]] and sold over 2 million copies in the U.S. Rhino also began releasing remastered versions of all of the band's Columbia-era albums. The following year, the band released their most comprehensive compilation to date in the form of a box set, simply titled ''[[The Box (Chicago album)|The Box]]''. In October 2003, Rhino reissued ''Chicago XXV: The Christmas Album'', along with six new recordings, as ''What's It Gonna Be, Santa?''.

The American cable music channel [[VH1]] featured the band in an episode of its ''[[Behind the Music]]'' series, "Chicago: Behind the Music", season 1, episode 133. The episode first aired on October 15, 2000.<ref name="VH1 2000">{{Cite web|url=http://www.vh1.com/episodes/syqlfr/behind-the-music-chicago-behind-the-music-133-season-1-ep-133|title=Chicago: Behind the Music #133|date=October 15, 2000|publisher=VH1|access-date=October 16, 2017|archive-url=https://web.archive.org/web/20171016231551/http://www.vh1.com/episodes/syqlfr/behind-the-music-chicago-behind-the-music-133-season-1-ep-133|archive-date=October 16, 2017|url-status=dead}}</ref>

In 2004, 2005, and 2009, Chicago toured with Earth, Wind & Fire.<ref>{{cite news|url=http://cnnwire.blogs.cnn.com/2009/03/10/chicago-earth-wind-fire-reunite-for-summer-tour|publisher=CNN|title=Chicago, Earth, Wind & Fire reunite for summer tour|access-date=April 28, 2010|url-status=dead|archive-url=https://archive.today/20090614083314/http://cnnwire.blogs.cnn.com/2009/03/10/chicago-earth-wind-fire-reunite-for-summer-tour|archive-date=June 14, 2009}}</ref>

On March 21, 2006, their first all-new studio album since ''Twenty 1'' arrived with ''[[Chicago XXX]]''. It was produced by [[Jay DeMarcus]], bassist/vocalist with the country trio [[Rascal Flatts]],<ref name="Las Vegas Sun">{{Cite news|url=https://lasvegassun.com/news/2006/mar/08/chicago-moving-to-las-vegas/|title=Chicago moving to Las Vegas?|date=March 8, 2006|publisher=Las Vegas Sun|access-date=October 1, 2017|location=Las Vegas, Nevada, USA|archive-url=https://web.archive.org/web/20171002022919/https://lasvegassun.com/news/2006/mar/08/chicago-moving-to-las-vegas/|archive-date=October 2, 2017|url-status=live}}</ref> who was a long-time fan of Chicago and had cited the group as an influence on him as a musician in a previous fan letter to Jason Scheff.<ref>{{Cite news|url=http://www.ocregister.com/2006/07/09/their-kind-of-band-chicago-is/|title=Their kind of band, Chicago is|date=July 9, 2006|work=Orange County Register|access-date=October 1, 2017|publisher=Southern California News Group|location=Anaheim, California, USA|language=en-US|archive-url=https://web.archive.org/web/20171002022419/http://www.ocregister.com/2006/07/09/their-kind-of-band-chicago-is/|archive-date=October 2, 2017|url-status=live}}</ref> It also marked the first time the band's music was available as a digital download. The album peaked at No. 41 in the U.S.,<ref name= "Chicago Billboard 200" /> spawning two minor adult contemporary hits: "Feel" and "Love Will Come Back". Two songs from this album, "Feel" and "Caroline", were performed live during Chicago's fall 2005 tour.

Chicago made multi-week appearances at the [[MGM Grand Las Vegas]] in March, May and October 2006.<ref name="Las Vegas Sun" /><ref>{{Cite news|url=https://www.reviewjournal.com/entertainment/entertainment-columns/mike-weatherford/chicago/|title=Chicago|last=Weatherford|first=Mike|date=October 10, 2008|work=Las Vegas Review-Journal|access-date=October 1, 2017|publisher=Las Vegas Review-Journal, Inc.|language=en-US|archive-url=https://web.archive.org/web/20171002022027/https://www.reviewjournal.com/entertainment/entertainment-columns/mike-weatherford/chicago/|archive-date=October 2, 2017|url-status=live}}</ref> In July 2006, the band made a series of U.S. appearances with [[Huey Lewis and the News]].<ref name=Curtin>{{Cite news|url=http://poststar.com/lifestyles/old-acts-show-some-flash-at-spac/article_53da0c25-78f9-5455-83a1-7202ca4afd3a.html|title=Old acts show some flash at SPAC|last=Curtin|first=Mike|date=July 27, 2006|work=Glens Falls Post-Star|access-date=September 30, 2017|publisher=Robert Forcey|location=Glens Falls, New York, USA|language=en|archive-url=https://web.archive.org/web/20170930222623/http://poststar.com/lifestyles/old-acts-show-some-flash-at-spac/article_53da0c25-78f9-5455-83a1-7202ca4afd3a.html|archive-date=September 30, 2017|url-status=live}}</ref>

On October 2, 2007, Rhino Records released the two-disc ''[[The Best of Chicago: 40th Anniversary Edition]]'' (''Chicago XXXI''), a new greatest hits compilation spanning their entire forty years, similar to ''[[The Very Best of: Only the Beginning]]'', released five years earlier.

In 2008, ''Stone of Sisyphus'' – once known as the aborted ''Chicago XXII'', now listed officially as ''Chicago XXXII'' – was released with an expanded format.<ref name="Payne June2008" /><ref name="LeRoy July2008" />

[[Drew Hester]], who was the percussionist and drummer for the [[Foo Fighters]], joined the band in January 2009 to temporarily fill in for an ill Imboden,<ref name=Pound>{{Cite web|url=http://staugustine.com/stories/040309/compass_040309_604.shtml|title=Chicago {{!}} StAugustine.com|last=Pound|first=Kara|date=April 3, 2009|publisher=staugustine.com|location=St. Augustine, Florida, U.S.A.|access-date=February 8, 2017|archive-url=https://web.archive.org/web/20170211155550/http://staugustine.com/stories/040309/compass_040309_604.shtml|archive-date=February 11, 2017|url-status=dead}}</ref> and continued with the band as a percussionist upon Imboden's return later in the year.<ref name="Lifton May2012">{{Cite web|url=http://ultimateclassicrock.com/drew-hester-leaves-chicago/|title=Drew Hester Leaves Chicago|last=Lifton|first=Dave|date=May 27, 2012|website=Ultimate Classic Rock|language=en-US|access-date=September 28, 2017|archive-url=https://web.archive.org/web/20170905053556/http://ultimateclassicrock.com/drew-hester-leaves-chicago/|archive-date=September 5, 2017|url-status=live}}</ref> In August 2009, Champlin was fired from the band.<ref>{{Cite interview|last=Champlin|first=Bill|subject-link=Bill Champlin|interviewer=Nick Deriso|url=http://somethingelsereviews.com/2011/06/01/something-else-interview-bill-champlin-formerly-of-chicago/|title=Bill Champlin, formerly of Chicago: Something Else! Interview|date=June 1, 2011|website=Something ELSE!|language=en-US|access-date=September 28, 2017|archive-url=https://web.archive.org/web/20170922050628/http://somethingelsereviews.com/2011/06/01/something-else-interview-bill-champlin-formerly-of-chicago/|archive-date=September 22, 2017|url-status=live}}</ref> He was replaced by Grammy-nominated keyboardist [[Lou Pardini]], who had worked with [[Stevie Wonder]] and [[Santana (band)|Santana]].<ref name="CNN Aug2009">{{Cite web|url=http://www.cnn.com/2009/SHOWBIZ/Music/08/10/chicago.champlin/|title=Musician Bill Champlin leaves Chicago|last=Payne|first=Ed|date=August 11, 2009|publisher=CNN|language=en|access-date=September 28, 2017|archive-url=https://web.archive.org/web/20170929000706/http://www.cnn.com/2009/SHOWBIZ/Music/08/10/chicago.champlin/|archive-date=September 29, 2017|url-status=live}}</ref>

=== 2010s ===
In 2010 (just as they had already done in 1999 and 2008), Chicago toured with [[the Doobie Brothers]] (and would do so again in 2017).<ref>{{Cite web|url=https://www.ticketnews.com/chicago-doobie-brothers-tour-rolls-out-co-headlining-dates-for-summer-2010/|title=Chicago, Doobie Brothers tour rolls out co-headlining dates for summer 2010 {{!}} TicketNews|last=Reitz|first=Allison|date=December 18, 2009|website=www.ticketnews.com|publisher=TicketNews|language=en-US|access-date=September 28, 2017|archive-url=https://web.archive.org/web/20170929045107/https://www.ticketnews.com/chicago-doobie-brothers-tour-rolls-out-co-headlining-dates-for-summer-2010/|archive-date=September 29, 2017|url-status=live}}</ref> A 2011 performance in [[Chicago]] became a video for the [[HDNet]] cable channel that featured the Doobie Brothers joining Chicago for three encore tunes.<ref>{{Cite web|url=http://moviecitynews.com/2012/page/235/|title=Movie City News: Chicago in Chicago: Blu-ray|last=Dretzka|first=Gary|date=June 14, 2012|website=moviecitynews.com|language=en-US|access-date=September 28, 2017|archive-url=https://web.archive.org/web/20170928225645/http://moviecitynews.com/2012/page/235/|archive-date=September 28, 2017|url-status=dead}}</ref> The band also appeared on the season nine finale of ''[[American Idol]]''.<ref>{{cite news|last=Berman|first=Craig|title='Idol' voters make DeWyze choice|url=https://www.nbcnews.com/id/wbna37367849|access-date=May 28, 2010|date=May 27, 2010|work=Today|archive-url=https://web.archive.org/web/20100528123214/http://today.msnbc.msn.com/id/37367849/ns/today-entertainment/|archive-date=May 28, 2010|url-status=live}}</ref> On July 24, 2011, the band performed at [[Red Rocks]] in Colorado, accompanied by the [[Colorado Symphony Orchestra]].<ref>{{Cite web|url=http://www.artscomplex.com/EventDisplay/tabid/123/Default.aspx?id=125712&bct=0&bcd=7/24/2011&bcv=0|title=Chicago with the Colorado Symphony|year=2011|website=artscomplex.com|publisher=City and County of Denver|language=en-US|access-date=September 28, 2017|archive-url=https://web.archive.org/web/20170928223755/http://www.artscomplex.com/EventDisplay/tabid/123/Default.aspx?id=125712&bct=0&bcd=7%2F24%2F2011&bcv=0|archive-date=September 28, 2017|url-status=dead}}</ref>

With ''[[Chicago XXXIII: O Christmas Three]],'' the band re-teamed with producer Ramone (he had previously released the new tracks for the expanded Christmas re-release ''What's It Gonna Be, Santa?'') to record a new Christmas album.<ref name="UCM Sept 28, 2011">{{Cite web|url=http://ultimateclassicrock.com/chicago-holiday-album-release-date/|title=Chicago Reveal More Details About Holiday Album|last=Wardlaw|first=Matt|date=September 28, 2011|website=Ultimate Classic Rock|publisher=Loudwire Network|language=en-US|access-date=September 29, 2017|archive-url=https://web.archive.org/web/20170929052112/http://ultimateclassicrock.com/chicago-holiday-album-release-date/|archive-date=September 29, 2017|url-status=live}}</ref> [[Dolly Parton]] was a guest artist on the album,<ref name="UCM Sept 28, 2011" /> which was released in October 2011. In the meantime, Rhino released ''[[Chicago XXXIV: Live in '75]]'', a two-disc set containing two hours of previously unreleased performances recorded June 24–26, 1975 at the [[Capital Centre (Landover, Maryland)|Capital Centre]] in [[Largo, Maryland]], featuring the original members of Chicago performing some of their greatest hits up to that point. In 2012, Chicago and the Doobie Brothers held another joint tour.<ref>{{cite web|url=http://ultimateclassicrock.com/chicago-and-doobie-brothers-announce-2012-tour/|title=Chicago and Doobie Brothers Announce 2012 Tour|publisher=Ultimateclassicrock.com|date=June 27, 2012|access-date=September 26, 2012|archive-url=https://web.archive.org/web/20121025215610/http://ultimateclassicrock.com/chicago-and-doobie-brothers-announce-2012-tour/|archive-date=October 25, 2012|url-status=live}}</ref> That same year, Hester left the group shortly before the tour,<ref name="Lifton May2012" /> and was succeeded at first by percussionist [[Daniel de los Reyes]],<ref name=Santos>{{Cite news|url=http://www.expressnews.com/entertainment/music-stage/article/After-nearly-50-years-Chicago-still-on-the-road-6245294.php|title=After nearly 50 years, Chicago still on the road and rocking|last=Santos|first=Sandra|date=May 6, 2015|newspaper=San Antonio Express-News|quote=Chicago’s newest member, percussionist Walfredo Reyes Jr., came to the band in a fun way a few years ago, Scheff said. Reyes’ brother, percussionist Daniel de los Reyes, was originally touring with the band, but had also been playing with the [[Zac Brown Band]]. When scheduling conflicts arose, Reyes would fill in for his brother. De Los Reyes eventually joined the Zac Brown Band on their tour full-time, so Reyes was invited to join Chicago full-time, as well.|access-date=February 10, 2017|archive-url=https://web.archive.org/web/20170211083226/http://www.expressnews.com/entertainment/music-stage/article/After-nearly-50-years-Chicago-still-on-the-road-6245294.php|archive-date=February 11, 2017|url-status=live}}</ref><ref>{{cite web|title=Front Row King|url=http://www.frontrowking.com/buy-chicago-the-band-concert-tickets/index.html|access-date=February 23, 2014|archive-url=https://web.archive.org/web/20140210120047/http://www.frontrowking.com/buy-chicago-the-band-concert-tickets/index.html|archive-date=February 10, 2014|url-status=dead}}</ref> then by Daniel's brother and former long-term [[Santana (band)|Santana]] member, [[Walfredo Reyes Jr.]]<ref name=Santos /><ref name="Walfredo Reyes Jr. at Chicago">{{cite web|title=Walfredo Reyes Jr.|publisher=Chicago|url=http://www.chicagotheband.com/walfredo-reyes-jr.html|access-date=May 1, 2013|url-status=dead|archive-url=https://web.archive.org/web/20130515104230/http://www.chicagotheband.com/walfredo-reyes-jr.html|archive-date=May 15, 2013}}</ref><ref name="Walfredo Reyes Jr. official web site">{{cite web|title=Walfredo Reyes Jr.|publisher=Walfredo Reyes Jr.|url=http://walfredoreyesjr.com/|access-date=April 24, 2013|archive-url=https://web.archive.org/web/20131003223510/http://www.walfredoreyesjr.com/|archive-date=October 3, 2013|url-status=live}}</ref>

In 2013, Lamm, Loughnane, Pankow, and Parazaider appeared in the [[HBO]] film ''[[Clear History]]'' as the band Chicago.<ref name= "Clear History IMDB">"Clear History" -[https://www.imdb.com/title/tt2279864/fullcredits?ref_=tt_cl_sm#cast IMDB] {{webarchive |url=https://web.archive.org/web/20160404110627/http://www.imdb.com/title/tt2279864/fullcredits?ref_=tt_cl_sm#cast |date=April 4, 2016 }}</ref> In late 2013, the band began releasing singles for a new album, starting with "Somethin' Comin', I Know" in August, "America" in September, "Crazy Happy" in December 2013, and "Naked in the Garden of Allah" in January 2014. The album, titled ''[[Chicago XXXVI: Now]]'', was released on July 4, 2014.<ref>{{cite web|url=https://www.chicagotheband.com/albums/chicago36.html|title="Now" Chicago XXXVI|publisher=Chicago Records|access-date=April 14, 2014|archive-url=https://web.archive.org/web/20170112171836/http://www.chicagotheband.com/albums/chicago36.html|archive-date=January 12, 2017|url-status=dead}}</ref>

The group's debut album, ''[[Chicago Transit Authority (album)|Chicago Transit Authority]]'', released in 1969, was inducted into the [[Grammy Hall of Fame]] in 2014.<ref name=":3" /> On January 25 and 28, 2014 Chicago performed two concerts with the [[Chicago Symphony Orchestra]].<ref>{{cite web|title=Chicago returns home—to the Chicago Symphony Orchestra |url=https://csosoundsandstories.org/chicago-returns-home-to-the-chicago-symphony-orchestra/ |website= CSO Sounds and Stories|last=Polkow|first=Dennis|publisher=Chicago Symphony Orchestra Association|date=January 8, 2014|access-date=August 26, 2018|archive-url=https://web.archive.org/web/20180904173644/https://csosoundsandstories.org/chicago-returns-home-to-the-chicago-symphony-orchestra/|archive-date=September 4, 2018}}</ref> In February 2015, Chicago released a two-disc live album, ''Chicago at Symphony Hall'', of their performances with the Chicago Symphony Orchestra.<ref>{{cite web |url=https://www.allmusic.com/album/chicago--symphony-hall-mw0003007447 |title=Chicago at Symphony Hall |publisher=AllMusic |date=September 4, 2018 |access-date=September 4, 2018 |archive-url=https://web.archive.org/web/20180904230109/https://www.allmusic.com/album/chicago--symphony-hall-mw0003007447 |archive-date=September 4, 2018 |url-status=live  }}</ref><ref>{{cite web |url=https://www.facebook.com/Chicago.Official/posts/chicago-is-proud-to-announce-a-new-live-album-chicago-at-symphony-hall-featuring/846715282054991/ |title=Chicago at Symphony Hall |last=Chicago (Official Page) |via=Facebook |date=September 4, 2018 |access-date=September 4, 2018 |archive-url=https://web.archive.org/web/20190320024210/https://www.facebook.com/Chicago.Official/posts/chicago-is-proud-to-announce-a-new-live-album-chicago-at-symphony-hall-featuring/846715282054991/ |archive-date=March 20, 2019 |url-status=live  }}</ref>{{Primary source inline|date=November 2020}}

In 2015, Chicago was listed among the nominees for induction into the [[Rock and Roll Hall of Fame]].<ref>{{cite magazine|url=https://www.billboard.com/articles/news/6722672/rock-and-roll-hall-of-fame-2016-nominees-cheap-trick-chicago-react|title=Rock and Roll Hall of Fame 2016 Nominees: Cheap Trick, Chicago & More React|last=Stutz|first=Colin|date=October 8, 2015|magazine=Billboard|access-date=October 28, 2015|archive-url=https://web.archive.org/web/20151015003619/http://www.billboard.com/articles/news/6722672/rock-and-roll-hall-of-fame-2016-nominees-cheap-trick-chicago-react|archive-date=October 15, 2015|url-status=live}}</ref> The original lineup – Cetera, Kath, Lamm, Loughnane, Pankow, Parazaider, and Seraphine – was inducted at the 31st annual Rock and Roll Hall of Fame induction ceremony on April 8, 2016, along with [[N.W.A]]., [[Deep Purple]], [[Steve Miller (musician)|Steve Miller]], and [[Cheap Trick]].<ref>{{cite web|url=http://ultimateclassicrock.com/2016-rock-and-roll-hall-of-fame-inductees/|title=Cheap Trick, Chicago, Deep Purple + Steve Miller Elected into the Rock and Roll Hall of Fame|publisher=Ultimateclassicrock.com|date=December 17, 2015|access-date=April 10, 2016|archive-url=https://web.archive.org/web/20160417020249/http://ultimateclassicrock.com/2016-rock-and-roll-hall-of-fame-inductees/|archive-date=April 17, 2016|url-status=live}}</ref> In February 2016, it was announced that original drummer Danny Seraphine would join the current lineup of Chicago for the first time in over 25 years for the Hall of Fame Induction Ceremony.<ref>{{cite web|title=Original 'Chicago' Drummer & Co-Founder Danny Seraphine to Perform at Hall of Fame Induction Ceremony|url=http://www.broadwayworld.com/bwwmusic/article/Original-Chicago-Drummer-Co-Founder-Danny-Seraphine-to-Perform-at-Hall-of-Fame-Induction-Ceremony-20160210|website=BWW|access-date=February 16, 2016|archive-url=https://web.archive.org/web/20160222013345/http://www.broadwayworld.com/bwwmusic/article/Original-Chicago-Drummer-Co-Founder-Danny-Seraphine-to-Perform-at-Hall-of-Fame-Induction-Ceremony-20160210|archive-date=February 22, 2016|url-status=live}}</ref> Peter Cetera chose not to attend.<ref name="Ives April 2016">{{Cite news|url=http://news.radio.com/2016/04/08/rock-hall-induction-ceremony-2016-wrap-up-cheap-trick-n-w-a-and-more/|title=Rock Hall Induction Ceremony 2016 Wrap-Up: Cheap Trick, N.W.A. and More|last=Ives|first=Brian|date=April 8, 2016|work=Radio.com|access-date=September 28, 2017|publisher=CBS Radio, Inc.|language=en-US}}{{dead link|date=September 2023}}</ref><ref>{{Cite magazine|url=https://www.rollingstone.com/music/music-news/chicagos-robert-lamm-talks-peter-cetera-absence-at-rock-hall-225418/|title=Chicago's Robert Lamm Talks Peter Cetera Absence at Rock Hall|author=<!--Staff writer(s); no by-line.-->|date=April 9, 2016|magazine=Rolling Stone|access-date=October 30, 2021|archive-url=https://web.archive.org/web/20211029114615/https://www.rollingstone.com/music/music-news/chicagos-robert-lamm-talks-peter-cetera-absence-at-rock-hall-225418/|archive-date=October 29, 2021|language=en-US|url-status=live}}</ref> Terry Kath's daughter Michelle accepted her father's award.<ref name="Ives April 2016" /> 
Chicago and Earth, Wind & Fire embarked on another tour together in 2015 and 2016.<ref>{{cite web|url=https://www.musictimes.com/articles/54382/20151113/chicago-earth-wind-fire-announce-2016-heart-soul-tour-2.htm |title=Chicago and Earth, Wind & Fire Announce 2016 Heart And Soul Tour 2.0 |first=Michael|last=Haskoor|publisher=Music Times, LLC|date=November 13, 2015|access-date=September 8, 2018|archive-url=https://web.archive.org/web/20161006194338/https://www.musictimes.com/articles/54382/20151113/chicago-earth-wind-fire-announce-2016-heart-soul-tour-2.htm|archive-date=October 6, 2016|language=en-US}}</ref> In July 2016, Chicago performed on ABC's ''[[Greatest Hits (TV series)|Greatest Hits]]''.<ref>{{Cite magazine|url=https://www.rollingstone.com/music/news/bonnie-raitt-miguel-chicago-among-eclectic-greatest-hits-tv-lineup-20160601|title=Bonnie Raitt, Miguel, Chicago in 'Greatest Hits' TV Lineup|last=Legaspi|first=Althea|date=June 1, 2016|magazine=Rolling Stone|access-date=October 2, 2017|archive-url=https://web.archive.org/web/20171003030422/http://www.rollingstone.com/music/news/bonnie-raitt-miguel-chicago-among-eclectic-greatest-hits-tv-lineup-20160601|archive-date=October 3, 2017|url-status=live|language=en-US}}</ref><ref>{{cite web|url=http://abc.go.com/shows/greatest-hits/video/most-recent/VDKA0_536rcaum|title=Watch Chicago and Aloe Blacc Sing You're The Inspiration on Greatest Hits|publisher=American Broadcasting Company|access-date=October 2, 2017|archive-url=https://web.archive.org/web/20171003075115/http://abc.go.com/shows/greatest-hits/video/most-recent/VDKA0_536rcaum|archive-date=October 3, 2017|language=en-US|url-status=dead}}</ref>

On September 23, 2016, a documentary called ''The Terry Kath Experience'' was released.<ref>{{cite web|url=https://www.imdb.com/title/tt5037288/|title=The Terry Kath Experience|website=[[IMDb]]|access-date=December 6, 2021|archive-url=https://web.archive.org/web/20211112094328/https://www.imdb.com/title/tt5037288/|archive-date=November 12, 2021|language=en-US|url-status=live}}</ref> The documentary featured most of the members of Chicago talking about Kath's life (most notably Kath's second wife Camelia Kath and original Chicago bassist Peter Cetera).<ref name="Hollywood Reporter September2016">{{Cite web|last=Dalton|first=Stephen|date=September 23, 2016|title='The Terry Kath Experience': Film Review {{!}} TIFF 2016|url=https://www.hollywoodreporter.com/movies/movie-reviews/terry-kath-experience-review-932302/|access-date=December 6, 2021|website=The Hollywood Reporter|archive-url=https://web.archive.org/web/20211207045629/https://www.hollywoodreporter.com/movies/movie-reviews/terry-kath-experience-review-932302/|archive-date=December 7, 2021|language=en-US|url-status=live}}</ref><ref name="RS December2016">{{Cite magazine|last=Chiu|first=David|date=December 11, 2017|title=Chicago's Terry Kath: Inside Guitarist's Life and Tragic Death|url=https://www.rollingstone.com/music/music-features/chicagos-terry-kath-inside-the-life-and-tragic-death-of-an-unsung-guitar-hero-201725/|access-date=December 6, 2021|magazine=[[Rolling Stone]]|archive-date=January 8, 2021|language=en-US|url-status=live|archive-url=https://web.archive.org/web/20210108033906/https://www.rollingstone.com/music/music-features/chicagos-terry-kath-inside-the-life-and-tragic-death-of-an-unsung-guitar-hero-201725/}}</ref> It was directed by Kath's daughter, Michelle Kath Sinclair.<ref name="Hollywood Reporter September2016"/><ref name="RS December2016"/>

After taking a temporary leave in May 2016, citing "family health reasons",<ref name="Sands Oct2016">{{Cite news|url=http://forbassplayersonly.com/jason-scheff-leaves-chicago/|title=Jason Scheff leaves Chicago|last=Sands|first=David|date=October 27, 2016|work=For Bass Players Only|access-date=September 28, 2016|language=en-US|archive-url=https://web.archive.org/web/20161031215937/http://forbassplayersonly.com/jason-scheff-leaves-chicago/|archive-date=October 31, 2016|url-status=dead}}</ref><ref>{{cite web|last=Payne|first=Ed|url=https://www.linkedin.com/pulse/chicagos-jason-scheff-fired-hasnt-quit-band-source-says-ed-payne|title=Chicago's Jason Scheff 'not fired,' hasn't quit the band, source says|date=May 4, 2016|website=linkedin.com|access-date=July 19, 2017|archive-url=https://web.archive.org/web/20190320024211/https://www.linkedin.com/pulse/chicagos-jason-scheff-fired-hasnt-quit-band-source-says-ed-payne|archive-date=March 20, 2019|url-status=live}}</ref> it was announced on October 25, 2016, that Jason Scheff had left Chicago after 31 years.<ref name="Sands Oct2016" /><ref>{{cite web|url=http://www.antimusic.com/news/16/October/27Chicagos_Jason_Scheff_Leaves_Band_After_30_Years.shtml|title=Chicago's Jason Scheff Leaves Band After 30 Years ::Chicago News ::antiMusic.com|website=antimusic.com|access-date=July 19, 2017|archive-url=https://web.archive.org/web/20170922051253/http://www.antimusic.com/news/16/October/27Chicagos_Jason_Scheff_Leaves_Band_After_30_Years.shtml|archive-date=September 22, 2017|url-status=live}}</ref> Bassist/vocalist [[Jeff Coffey]], who had been filling in for Scheff during his absence, was promoted to a full-time member.<ref>{{cite web|last1=Nick|first1=DeRiso|title=Chicago Replace Longtime Singer and Bassist Jason Scheff|url=http://ultimateclassicrock.com/chicago-jason-scheff/|website=Ultimate Classic Rock|date=October 25, 2016 |access-date=November 2, 2016|archive-url=https://web.archive.org/web/20161104000238/http://ultimateclassicrock.com/chicago-jason-scheff/|archive-date=November 4, 2016|url-status=live}}</ref> Saxophonist [[Ray Herrmann]], who had previously filled in for Parazaider on various tour dates since 2005, also became an official member at this time after Parazaider retired permanently from the road.<ref name="Sculley July2017">{{Cite news|url=https://pilotonline.com/entertainment/music/original-chicago-member-still-rockin-after-years-doesn-t-mince/article_8cb5859f-ab07-5419-98e6-9794c8850ec8.html|title=Original Chicago member, still rockin' after 50 years, doesn't mince words|last=Sculley|first=Alan|date=July 27, 2017|work=Virginian-Pilot|access-date=September 27, 2017|quote="Parazaider is still a band member and performs with the group for certain events."|location=Norfolk, Virginia, USA|language=en-US|archive-url=https://web.archive.org/web/20181006154825/https://pilotonline.com/entertainment/music/original-chicago-member-still-rockin-after-years-doesn-t-mince/article_8cb5859f-ab07-5419-98e6-9794c8850ec8.html|archive-date=October 6, 2018|url-status=dead}}</ref>  Although Parazaider retired from regular touring, he remained a band member.<ref name="TribLive2018">{{Cite news|url=https://triblive.com/aande/music/13901189-74/chicago-to-features-new-blood-classic-hits-at-keybank-pavilion-show|title=Chicago Brings New Blood, Classic Hits to KeyBank Pavilion|last=Sculley|first=Alan|work=TribLive|date=July 25, 2018|access-date=September 23, 2018|quote="Original saxophonist Walt Parazaider remains a member of Chicago, but no longer tours on a regular basis with the group."|archive-url=https://web.archive.org/web/20180923052525/https://triblive.com/aande/music/13901189-74/chicago-to-features-new-blood-classic-hits-at-keybank-pavilion-show|archive-date=September 23, 2018|url-status=live|language=en-US}}</ref><ref name="Sculley July2017"/>

In January 2017, [[CNN Films]] aired a two-hour biographical documentary film on the group titled ''Now More Than Ever: The History of Chicago.''<ref name="CNN Press Release">{{cite press release|title=CNN Films Premieres 'Now More Than Ever: The History of Chicago' on New Year's Day|date=December 15, 2016|publisher=Cable News Network|url=http://cnnpressroom.blogs.cnn.com/2016/12/15/cnn-films-premieres-now-more-than-ever-the-history-of-chicago-on-new-years-day/|access-date=September 28, 2017|author=<!--Staff writer(s); no by-line.-->|archive-url=https://web.archive.org/web/20170929091542/http://cnnpressroom.blogs.cnn.com/2016/12/15/cnn-films-premieres-now-more-than-ever-the-history-of-chicago-on-new-years-day/|archive-date=September 29, 2017|url-status=dead}}</ref> The film was directed and edited by Peter Pardini, nephew of band member Lou Pardini, and produced by the band.<ref name=Farhi>{{cite news |last=Farhi |first=Paul |date=January 4, 2017 |url=https://www.washingtonpost.com/lifestyle/style/why-did-cnn-air-a-documentary-about-the-band-chicago-produced-by-band-members/2017/01/04/dc47f2b8-d1d5-11e6-9cb0-54ab630851e8_story.html |title=Why did CNN air a documentary about the band Chicago produced by band members? |newspaper=[[The Washington Post]] |access-date=September 28, 2017 |archive-url=https://web.archive.org/web/20171004035049/https://www.washingtonpost.com/lifestyle/style/why-did-cnn-air-a-documentary-about-the-band-chicago-produced-by-band-members/2017/01/04/dc47f2b8-d1d5-11e6-9cb0-54ab630851e8_story.html |archive-date=October 4, 2017 |url-status=live  }}</ref> The film's premiere was the highest-rated program in the 25–54 demographic.<ref>{{cite web|url=https://www.imdb.com/title/tt3807496/|title=Now More Than Ever: The History of Chicago|website=[[IMDb]]|access-date=January 17, 2018|archive-url=https://web.archive.org/web/20180307221128/http://www.imdb.com/title/tt3807496/|archive-date=March 7, 2018|url-status=live}}</ref> The film won the 2016 "Best of the Fest" Audience Choice Award at the [[Sedona Film Festival|Sedona International Film Festival]].<ref>{{Cite web|url=http://www.sedonafilmfestival.org/Page.asp?NavID=89|title=Sedona Film Festival - Award Winners: Past Festivals|website=sedonafilmfestival.org|access-date=September 28, 2017|archive-url=https://web.archive.org/web/20141209025237/http://www.sedonafilmfestival.org/Page.asp?NavID=89|archive-date=December 9, 2014|url-status=live}}</ref> At the 10th Annual Fort Myers Beach Film Festival in 2016, it won the "People's Choice" award and Peter Pardini won the "Rising Star Award" as director and filmmaker.<ref>{{Cite news|url=https://fortmyersbeach.news/film-festival-awards/|title=Film Festival Awards|author=<!--Staff writer(s); no by-line.-->|date=April 28, 2016|work=Island Sand Paper{{!}}Fort Myers Beach News|access-date=September 28, 2017|language=en-US|archive-url=https://web.archive.org/web/20170929091217/https://fortmyersbeach.news/film-festival-awards/|archive-date=September 29, 2017|url-status=live}}</ref>

On February 22, 2017, it was announced that Cetera, Lamm, and Pankow were among the 2017 [[Songwriters Hall of Fame]] inductees for their songwriting efforts as members of Chicago.<ref name=SongHallFeb2017 /><ref name=CBSFeb2017 /> The induction event was held Thursday, June 15 at the [[New York Marriott Marquis|Marriott Marquis]] Hotel in New York City.<ref name=SongHallFeb2017 />
<!-- Deleted image removed: [[File:Chicago Horns.png|thumb|right|The Chicago horn section performing in 2017, Pankow, Hermann and Loughnane (left to right)]] -->
Chicago's website stated that in 2017, the band was working on a new album, ''Chicago XXXVII''.<ref name= "Chicago News 2/22/17">{{Cite web|url=https://www.chicagotheband.com/news/news-main.html|title=Chicago's Robert Lamm and James Pankow to be Inducted into Songwriters Hall of Fame|date=February 22, 2017|website=chicagotheband.com|archive-url=https://web.archive.org/web/20170101221702/http://chicagotheband.com/news/news-main.html|archive-date=January 1, 2017|url-status=dead|access-date=February 9, 2018}}</ref>

On September 17, 2017, former percussionist Laudir de Oliveira died of a heart attack while performing onstage in his native [[Rio de Janeiro]].<ref>{{cite web|url=https://oglobo.globo.com/cultura/percussionista-laudir-de-oliveira-morre-aos-77-anos-21835178|title=Percussionista Laudir de Oliveira morre, aos 77 anos|date=September 17, 2017|language=pt|access-date=September 17, 2017|archive-url=https://web.archive.org/web/20170918021549/https://oglobo.globo.com/cultura/percussionista-laudir-de-oliveira-morre-aos-77-anos-21835178|archive-date=September 18, 2017|url-status=live}}</ref><ref>{{Cite news|url=http://womc.cbslocal.com/2017/09/18/chicago-longtime-percussionist-laudir-de-oliveira-has-died/|title=Chicago: Longtime Percussionist Laudir de Oliveira Has Died|last=Johnson|first=Jim|date=September 18, 2017|work=104.3 WOMC|access-date=October 19, 2017|publisher=CBS Radio Inc.|location=Detroit, Michigan, USA|language=en|archive-url=https://web.archive.org/web/20171019220726/http://womc.cbslocal.com/2017/09/18/chicago-longtime-percussionist-laudir-de-oliveira-has-died/|archive-date=October 19, 2017|url-status=dead}}</ref>

Chicago began their 2018 touring schedule on Saturday, January 13 by performing the grand opening concert at the new [[Xcite Center]] at [[Parx Casino]] in [[Bensalem, Pennsylvania]].<ref name=Vineberg>{{cite news |last=Vineberg |first=Andy |date=January 14, 2018 |url=http://www.buckscountycouriertimes.com/news/20180113/chicago-gets-parx-casinos-new-xcite-center-off-to-rousing-start |title=Chicago gets Parx Casino's new Xcite Center off to rousing start |newspaper=Bucks County Courier Times |publisher=GateHouse Media, LLC |access-date=February 4, 2018 |archive-url=https://web.archive.org/web/20180206190302/http://www.buckscountycouriertimes.com/news/20180113/chicago-gets-parx-casinos-new-xcite-center-off-to-rousing-start |archive-date=February 6, 2018 |url-status=live  }}</ref>

On Wednesday, January 17, 2018, drummer Tris Imboden announced he was leaving the band after 27 years to spend more time with his family.<ref name="Two Chicago Members Leaving Band">{{cite web|url=http://bestclassicbands.com/chicago-band-members-leaving-1-19-18/|title=Two Chicago Members Leaving Band|publisher=Bestclassicbands.com|date=January 19, 2018|access-date=February 4, 2018|archive-url=https://web.archive.org/web/20180205184408/http://bestclassicbands.com/chicago-band-members-leaving-1-19-18/|archive-date=February 5, 2018|url-status=live}}</ref> On Friday, January 19, 2018, bassist and vocalist Jeff Coffey announced on his [[Facebook]] page that he was also departing from the band due to its heavy touring schedule.<ref name="Two Chicago Members Leaving Band"/> Chicago announced that percussionist Walfredo Reyes Jr. was moving over to drums, replacing Imboden.<ref>{{Cite web|url=http://beatosblog.com/chicago-done-right-wally-reyes-jr-named-new-drummer/|title=Chicago Done Right; Wally Reyes, Jr. Named As The New Drummer|last=Biedzynski|first=Ken|date=January 20, 2018|website=beatosblog.com|publisher=Beato's Blog|access-date=February 4, 2018|archive-url=https://web.archive.org/web/20180205130014/http://beatosblog.com/chicago-done-right-wally-reyes-jr-named-new-drummer/|archive-date=February 5, 2018|url-status=live}}</ref> Vocalist [[Neil Donell]], of Chicago tribute band Brass Transit, was chosen as the band's new lead singer and session musician Brett Simons also joined the band as their new bassist.<ref name=":1">{{Cite news|url=http://www.kfvs12.com/story/37307108/jeff-coffey-exits-chicago-second-member-to-leave-in-a-week|title=Lead singer Jeff Coffey exits Chicago, second member to leave band in a week|last=Payne|first=Ed|date=January 20, 2018|work=12 KFVS|access-date=January 22, 2018|location=Cape Girardeau, Missouri, U.S.A.|language=en|archive-url=https://web.archive.org/web/20180123072329/http://www.kfvs12.com/story/37307108/jeff-coffey-exits-chicago-second-member-to-leave-in-a-week|archive-date=January 23, 2018|url-status=dead}}</ref><ref name=":0">{{Cite web|url=http://ultimateclassicrock.com/tris-imboden-chicago/|title=Drummer Tris Imboden Quits Chicago|last=Lifton|first=Dave|date=January 21, 2018|website=Ultimate Classic Rock|access-date=January 22, 2018|archive-url=https://web.archive.org/web/20180122235112/http://ultimateclassicrock.com/tris-imboden-chicago/|archive-date=January 22, 2018|url-status=live}}</ref> Daniel de los Reyes' return to the percussion position was announced, filling the vacancy left by his brother's move to the drumset.<ref name="Chicago news 1/29/18">{{Cite web|url=http://www.chicagotheband.com/news/2018-tour.html|title=Chicago Kicks Off Their 2018 Tour|date=January 29, 2018|website=chicagotheband.com|archive-url=https://web.archive.org/web/20180130154332/http://chicagotheband.com/news/2018-tour.html|archive-date=January 30, 2018|url-status=dead|access-date=January 31, 2018}}</ref><ref>{{Cite news|url=https://themusicuniverse.com/chicago-performing-chicago-ii-entirety/|title=Chicago performing 'Chicago II' in entirety {{!}} The Music Universe|last=Iahn|first=Buddy|date=January 29, 2018|work=The Music Universe|access-date=January 31, 2018|language=en-US|archive-url=https://web.archive.org/web/20180131203425/https://themusicuniverse.com/chicago-performing-chicago-ii-entirety/|archive-date=January 31, 2018|url-status=live}}</ref>

On April 6, 2018, Chicago released ''Chicago: VI Decades Live (This is What We Do)'', a box set chronicling the band's live performances throughout their history.<ref>{{cite web |url=https://ultimateclassicrock.com/chicago-vi-decades-live/ |title=Chicago Announce 'VI Decades Live' Box |first=Jeff |last=Giles |website=Ultimate Classic Rock |publisher=Loudwire Network |date=February 12, 2018 |access-date=August 26, 2018 |archive-url=https://web.archive.org/web/20180803163711/http://ultimateclassicrock.com/chicago-vi-decades-live/ |archive-date=August 3, 2018 |url-status=live  }}</ref>

In May 2018, it was revealed that percussionist Daniel de los Reyes was departing Chicago to go back to his other group, the Zac Brown Band.<ref name="Chicago: The world’s longest encore">{{Cite news|url=http://www.connectsavannah.com/savannah/chicago-the-worlds-longest-encore/Content?oid=8377785|title=Chicago: 'The world's longest encore'|last=Sculley|first=Alan|date=May 16, 2018|publisher=Connect Savannah|access-date=May 19, 2018|location=Savannah, Georgia, U.S.A.|archive-url=https://web.archive.org/web/20180904174646/https://www.connectsavannah.com/savannah/chicago-the-worlds-longest-encore/Content?oid=8377785|archive-date=September 4, 2018|language=en}}</ref> On Thursday, May 17, 2018, Chicago announced on their official Facebook page and on their [[Twitter]] account that "Ray" Ramon Yslas had joined the band on percussion.

On June 29, 2018, Chicago released the album ''Chicago II: Live on Soundstage'', a live performance from November 2017 of the then current band lineup performing the entire second album.<ref>{{cite web|url=https://www.sunherald.com/news/local/news-columns-blogs/by-the-way/article181885271.html/ |title=Chicago's Robert Lamm on Revisiting 'Chicago II' and the Band's Long and Winding Road |first=Jeff |last=Clark |work=Sun Herald |date=October 31, 2017|access-date=September 4, 2018|archive-url=https://web.archive.org/web/20180904180144/https://www.sunherald.com/news/local/news-columns-blogs/by-the-way/article181885271.html|archive-date=September 4, 2018|language=en}}</ref><ref>{{cite web |url=https://www.allmusic.com/album/chicago-ii-live-on-soundstage-mw0003178448 |title=Chicago II: Live on Soundstage |first=Stephen Thomas |last=Erlewine |publisher=AllMusic |access-date=September 4, 2018 |archive-url=https://web.archive.org/web/20180904230054/https://www.allmusic.com/album/chicago-ii-live-on-soundstage-mw0003178448 |archive-date=September 4, 2018 |url-status=live  }}</ref>

In July 2018 the band updated its official web site, and no longer listed Parazaider as a member of the band.<ref name=":2">{{Cite web|url=https://chicagotheband.com/band-members/|title=Band Members – Chicago|website=chicagotheband.com|language=en-US|archive-url=https://web.archive.org/web/20180810235724/https://chicagotheband.com/band-members/|archive-date=August 10, 2018|url-status=dead|access-date=August 10, 2018}}</ref> Instead he is included on the band's "Tribute to Founding Members".<ref name="chicagotheband.com"/> Parazaider had retired from touring previously.<ref name="Sculley July2017" /><ref name="Durchholz">{{Cite news|url=https://www.stltoday.com/entertainment/music/reviews/chicago-delivers-a-satisfying-career-retrospective-but-pulls-a-political/article_2d6102bc-e38c-571c-be17-52de24d822c4.html|title=Chicago delivers a satisfying career retrospective but pulls a political punch|last=Durchholz|first=Daniel|date=June 22, 2017|work=stltoday.com|access-date=September 23, 2017|language=en|archive-url=https://web.archive.org/web/20170925121648/http://www.stltoday.com/entertainment/music/reviews/chicago-delivers-a-satisfying-career-retrospective-but-pulls-a-political/article_2d6102bc-e38c-571c-be17-52de24d822c4.html|archive-date=September 25, 2017|url-status=live}}</ref><ref name="Price NJHerald 2017">{{Cite news|url=http://www.njherald.com/20170810/chicago-feeling-50-years-young#|title=Chicago feeling 50 years young|last=Price|first=Robert|date=August 10, 2017|work=New Jersey Herald|access-date=August 21, 2017|language=en-US|archive-url=https://web.archive.org/web/20170822013415/http://www.njherald.com/20170810/chicago-feeling-50-years-young|archive-date=August 22, 2017|url-status=live}}</ref>

On October 26, 2018, Chicago released the album ''Chicago: Greatest Hits Live'', a live performance from 2017 for the [[PBS]] series ''[[Soundstage (TV series)|Soundstage]]''.<ref>{{cite web|url=https://bestclassicbands.com/chicago-live-albums-2018-9-25-18/ |title=Chicago to Release Live Albums From 1970 & 2017 |last=Best Classic Bands Staff |website=BestClassicBands.com |date=September 25, 2018|access-date=November 3, 2018|archive-url=https://web.archive.org/web/20181103194707/https://bestclassicbands.com/chicago-live-albums-2018-9-25-18/|archive-date=November 3, 2018|url-status=live|language=en-US}}</ref><ref>{{cite web|url=https://www.allmusic.com/album/greatest-hits-live-mw0003213176 |title=Chicago: Greatest Hits Live |publisher=AllMusic |access-date=November 3, 2018|archive-url=https://web.archive.org/web/20181103195809/https://www.allmusic.com/album/greatest-hits-live-mw0003213176|archive-date=November 3, 2018|url-status=live|language=en-US}}</ref>

On August 16, 2019, the band announced on their website that they would be releasing their fourth Christmas album, titled ''[[Chicago XXXVII: Chicago Christmas]]'', on October 4, 2019.<ref name="Chicago-Christmas">{{Cite web |url=https://chicagotheband.com/news/chicago-christmas-available-october-4th-from-rhino/ |title=The Legendary 'Rock Band With Horns' Gets Into The Spirit Of The Holiday Season With An Album That Mixes Original Christmas Songs And Yuletide Favorites |last= Chicago Media |website=Chicagotheband.com |date=August 16, 2019 |access-date=September 1, 2019 |archive-url=https://web.archive.org/web/20190901220339/https://chicagotheband.com/news/chicago-christmas-available-october-4th-from-rhino/ |archive-date=September 1, 2019 |url-status=live |language=en-US }}</ref><ref name="TheSecondDisc">{{Cite web |url=https://theseconddisc.com/2019/08/because-its-christmastime-chicago-releases-new-christmas-album-in-october/ |title=Because It's Christmastime: Chicago Releases New Christmas Album in October |first=Joe |last=Marchese |website=Theseconddisc.com |date=August 16, 2019 |access-date=September 15, 2019 |archive-url=https://web.archive.org/web/20191015162652/https://theseconddisc.com/2019/08/because-its-christmastime-chicago-releases-new-christmas-album-in-october/ |archive-date=October 15, 2019 |url-status=live |language=en-US  }}</ref> The album has a greater emphasis on original Christmas songs written by the group than their previous holiday albums.<ref name="Chicago-Christmas"/>

=== 2020s ===
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| footer            = Chicago performing in 2024 (clockwise from top left: [[Neil Donell]], Tony Obrohta, Eric Baines, [[Ray Herrmann]], [[Loren Gold]])
}}
Chicago received a [[Grammy Lifetime Achievement Award]] on October 16, 2020.<ref name="Grein Dec. 19, 2019"/><ref name= "Yglesias Oct. 16, 2020"/>

On April 19, 2021, Walter Parazaider released a statement that he has been diagnosed with Alzheimer's disease.<ref name="VCF">{{Cite web |url=https://vermilioncountyfirst.com/2021/04/19/chicago-co-founder-walt-parazaider-reveals-alzheimers-battle/#:~:text=Chicago%20co%2Dfounder%2C%20saxophonist%20and,informing%20fans%20of%20his%20situation. |title=Chicago Co-Founder Walt Parazaider Reveals Alzheimer's Battle |author=<!--Staff writer(s); no by-line.--> |website=Vermilion County First |date=April 19, 2021 |access-date=May 26, 2021 |archive-url=https://web.archive.org/web/20210527040204/https://vermilioncountyfirst.com/2021/04/19/chicago-co-founder-walt-parazaider-reveals-alzheimers-battle/#:~:text=Chicago%20co%2Dfounder%2C%20saxophonist%20and,informing%20fans%20of%20his%20situation. |archive-date=May 27, 2021 |url-status=live |language=en-US }}</ref>

During their 2021 summer tour, Lou Pardini was out for part of August and most of September, with [[The Who|Who]] keyboardist [[Loren Gold]] filling in until Pardini was able to return.<ref name="Louie">{{Cite web|url=https://allmusicmagazine.com/__chicago-is-back-in-colorado-springs-at-the-pikes-peak-center-8-24-21/|title=Chicago is Back in Colorado Springs at the Pikes Peak Center 8-24-21|last=Louie|first=Ray|date=August 27, 2021|website=AllMusicMagazine.com|publisher=All Music Magazine|access-date=September 28, 2021|archive-url=https://web.archive.org/web/20210928044544/https://allmusicmagazine.com/__chicago-is-back-in-colorado-springs-at-the-pikes-peak-center-8-24-21/|archive-date=September 28, 2021|url-status=live|language=en-US}}</ref> On November 15, 2021, Howland broke his arm in an accident and took a leave of absence from the band, with guitarist Tony Obrohta filling in for him at shows.<ref name="UCR-Dec2021">{{cite web|url=https://ultimateclassicrock.com/chicago-keith-howland-quit/|last1=Kielty|first1=Martin|title=Chicago's Longest-Tenured Guitarist Has Left the Band|website=[[Ultimate Classic Rock]]|date=December 2, 2021 |access-date=December 4, 2021|archive-url=https://web.archive.org/web/20211203092834/https://ultimateclassicrock.com/chicago-keith-howland-quit/|archive-date=December 3, 2021|url-status=live|language=en-US}}</ref> On December 1, 2021, Howland announced he was leaving Chicago after over 26 years, citing the recent accident and lengthy recovery period as bringing about the next phase of his life.<ref name="UCR-Dec2021"/> The band confirmed Howland's departure, and removed his name from band lineup page on their website.<ref name="UCR-Dec2021"/> Tony Obrohta officially joined the group to replace Howland in December 2021.<ref>{{cite web |url=https://chicagotheband.com/band-members/ |title=Chicago Band Members |publisher=Chicago |access-date=December 16, 2021 |archive-url=https://web.archive.org/web/20211217050756/https://chicagotheband.com/band-members/ |archive-date=December 17, 2021 |url-status=live |language=en-US  }}</ref><ref name="MRC">{{cite web|url=https://www.musicrecallmagazine.com/concert-reviews/chicago-is-well-worth-the-wait-in-augusta/|last=Hett|first=Joseph|title=Chicago Is Well Worth The Wait In Augusta|date=December 7, 2021|website=Musicrecallmagazine.com|access-date=December 16, 2021|archive-url=https://web.archive.org/web/20211217050551/https://www.musicrecallmagazine.com/concert-reviews/chicago-is-well-worth-the-wait-in-augusta/|archive-date=December 17, 2021|url-status=live|language=en-US}}</ref><ref name="OurQuadCities">{{cite web|url=https://www.ourquadcities.com/news/local-news/arts-and-culture/chicago-founder-and-songwriting-whiz-loving-life-after-55-years-with-band/|last=Turner|first=Jonathan|title=Chicago Founder and Songwriting Whiz Loving Life After 55 Years with Band|date=April 12, 2022|website=OurQuadCities.com|access-date=April 17, 2022|archive-url=https://web.archive.org/web/20220413113138/https://www.ourquadcities.com/news/local-news/arts-and-culture/chicago-founder-and-songwriting-whiz-loving-life-after-55-years-with-band/|archive-date=April 13, 2022|url-status=live|language=en-US}}</ref>

In November 2021, Chicago and [[Brian Wilson]] of the [[Beach Boys]] announced they will co-headline a 25 date tour in the summer of 2022.<ref name="Billboad-Dec2021">{{cite magazine|url=https://www.billboard.com/music/pop/chicago-brian-wilson-2022-summer-tour-1235003726/|last=Kaufman|first=Gil|title=Chicago, Brian Wilson Announce Co-Headlining Summer 2022 U.S. Tour|date=November 30, 2021|magazine=Billboard|access-date=December 5, 2021|archive-url=https://web.archive.org/web/20211130221147/https://www.billboard.com/music/pop/chicago-brian-wilson-2022-summer-tour-1235003726/|archive-date=November 30, 2021|url-status=live|language=en-US}}</ref><ref>{{Cite magazine|url=https://www.rollingstone.com/music/music-news/brian-wilson-chicago-co-headlining-summer-tour-1264723/|title=Brian Wilson and Chicago Announce Co-Headlining Summer Tour|last=Greene|first=Andy|date=November 30, 2021|magazine=Rolling Stone|access-date=December 5, 2021|archive-url=https://web.archive.org/web/20211202183956/https://www.rollingstone.com/music/music-news/brian-wilson-chicago-co-headlining-summer-tour-1264723/|archive-date=December 2, 2021|language=en-US|url-status=live}}</ref>

On January 21, 2022, Lou Pardini announced he was departing the band. Loren Gold (vocals, keyboards) appeared with the group on tour filling the role vacated by Pardini starting in January 2022, and on March 2, 2022, Chicago updated their website to list Gold as a band member.<ref>{{cite web |url=https://chicagotheband.com/band-members/ |title=Chicago Band Members |publisher=Chicago |access-date=March 7, 2022 |archive-url=https://web.archive.org/web/20220307052404/https://chicagotheband.com/band-members/ |archive-date=March 7, 2022 |url-status=live |language=en-US  }}</ref><ref name="ElPasoInc">{{Cite web |url=http://www.elpasoinc.com/lifestyle/chicago-packs-night-in-el-paso-with-hits-favorites/article_aa5d550c-9bfd-11ec-9880-a7a80527bb99.html |title=Chicago Packs Night in El Paso with Hits, Favorites |author=Vincent Arrieta |website=ElPasoInc.com |date=March 4, 2022 |access-date=March 7, 2022 |archive-url=https://web.archive.org/web/20220306045502/http://www.elpasoinc.com/lifestyle/chicago-packs-night-in-el-paso-with-hits-favorites/article_aa5d550c-9bfd-11ec-9880-a7a80527bb99.html |archive-date=March 6, 2022 |url-status=live |language=en-US  }}</ref><ref name="OurQuadCities"/> On Friday, May 6, 2022, Chicago announced on their website that Brett Simons had departed the band and Eric Baines (bass, vocals) had joined the group.<ref name="Chicago_Announcement">{{cite web |url=https://chicagotheband.com/news/another-chicago-chapter/ |title=Another Chicago Chapter |publisher=Chicago |access-date=May 8, 2022 |archive-url=https://web.archive.org/web/20220508041406/https://chicagotheband.com/news/another-chicago-chapter/ |archive-date=May 8, 2022 |url-status=live |language=en-US  }}</ref><ref name="RockCellarMagazine">{{cite web |url=https://www.rockcellarmagazine.com/chicago-if-this-is-goodbye-new-song-tour-dates-brian-wilson/ |title=New Chicago: Legendary Band Reflects with "If This Is Goodbye," Ahead of Co-Headline Tour with Brian Wilson |date=May 20, 2022 |author=<!--Staff writer(s); no by-line.--> |website=RockCellarMagazine.com |access-date=May 30, 2022 |archive-url=https://web.archive.org/web/20220520185022/https://www.rockcellarmagazine.com/chicago-if-this-is-goodbye-new-song-tour-dates-brian-wilson/ |archive-date=May 20, 2022 |url-status=live |language=en-US  }}</ref> The group also announced plans to release a new album in the summer of 2022.<ref name="Chicago_Announcement"/> Chicago released the single "If This Is Goodbye" on May 20, 2022.<ref name="RockCellarMagazine"/><ref name="UCR-May2022">{{cite web|url=https://ultimateclassicrock.com/chicago-if-this-is-goodbye/|last1=Rolli|first1=Bryan|title=Hear Chicago's Wistful New Song, "If This Is Goodbye"|date=May 20, 2022|website=[[Ultimate Classic Rock]]|access-date=May 30, 2022|archive-url=https://web.archive.org/web/20220526160250/https://ultimateclassicrock.com/chicago-if-this-is-goodbye/|archive-date=May 26, 2022|url-status=live|language=en-US}}</ref> On July 15, 2022, Chicago released ''[[Chicago XXXVIII: Born for This Moment]]''.<ref>{{Cite web |title=Chicago, the band on Twitter |url=https://twitter.com/chicagotheband/status/1547886403765170178 |access-date=July 16, 2022 |website=Twitter |language=en-US |archive-date=July 16, 2022 |archive-url=https://web.archive.org/web/20220716162400/https://twitter.com/chicagotheband/status/1547886403765170178 |url-status=live }}</ref> In November 2023, Chicago and Earth, Wind & Fire announced dates for the 2024 Heart and Soul joint tour.<ref name="HeartandSoul_2024">{{cite web|url=https://abcnews.go.com/GMA/Culture/chicago-earth-wind-fire-announce-2024-heart-soul/story?id=104882806|last1=Lances|first1=Jill|title=Chicago and Earth, Wind & Fire announce 2024 Heart & Soul Tour dates|date=November 14, 2023|website=[[ABC News (United States)|ABC News]]|access-date=November 20, 2023|archive-url=https://web.archive.org/web/20231115122848/https://abcnews.go.com/GMA/Culture/chicago-earth-wind-fire-announce-2024-heart-soul/story?id=104882806|archive-date=November 15, 2023|url-status=live|language=en-US}}</ref>