While starting work on original songs, at manager James William Guercio's request, the act moved to Los Angeles, California in June 1968, and signed with 'Columbia Records'. They then changed their name to Chicago Transit Authority. It was while performing regular at the Whisky a Go Go nightclub in West Hollywood that they got exposure to more musical artists of note of the time. Subsequently, they became the opening act for the likes of Janis Joplin and Jimi Hendrix.
Their first record, the eponymous Chicago Transit Authority (1969), was released as a double album; a rare event for a band's first release. Within a year, the record sold more than 1 million copies and was awarded platinum status. Among the tunes that made it a hit was Does Anybody Really Know What Time It Is?, Beginnings, Questions 67 and 68, and I'm a Man. The album was followed up with the posthumously released almost a decade later, Chicago Transit Authority Live in Toronto (1978), live recording of their performance in that Canadian city. After the original release, and perhaps realizing that municipal subways and buses had little to do with music, the act shortened their name to that of their city, Chicago.
Chicago (retroactively known as Chicago II; 1970) was another double-LP. The album's centerpiece track was the seven-part, 13-minute suite composed by Pankow called Ballet for a Girl in Buchannon. That suite yielded two top ten hits: Make Me Smile (reaching 9 US) and Color My World. The dynamic but cryptic 25 or 6 to 4, the act's first Top 5 hit) was also included on the record. The song is a reference to a songwriter trying to write at 25 or 26 minutes before 4 O'clock in the morning. Also included was the lengthy war-protest song It Better End Soon and Where Do We Go from Here?. The double-LP album's inner cover includes the playlist, the entire lyrics to It Better End Soon, and two quotations: "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."
Chicago III (1971) would contain two hit singles; Free from Lamm's Travel Suite would become the album's biggest hit.
Chicago at Carnegie Hall Volumes I, II, III, and IV were a set of 1971 recordings featuring live performances of tracks from their first three albums at that famous venue.
Their first single-disc release, Chicago V, reached number one on both the Billboard pop and jazz album charts. Featuring Saturday in the Park, a track that mixed everyday life and political desires in a more subtle way; it peaked at 3 on the Billboard Hot 100 in early 1972.
In 1973, Guercio produced and directed Electra Glide in Blue, a film about an Arizona motorcycle policeman.
1973's Chicago VI was the first of several albums to include Brazilian jazz percussionist Laudir de Oliveira and saw Cetera emerge as the main singer.
Chicago VII (1974) was another double-disc release.Chicago VIII (1975) featured the political allegory Harry Truman that achieved 13 on the Billboard Top 100, and the Pankow-composed Old Days that got a 5 on the Billboard Top 100 chart.
Chicago X (1976) features Cetera's ballad If You Leave Me Now, which held the top spot in the US charts for two weeks and the UK charts for three. The track became the group's first number one single, and won the act their only Grammy Award to date, the 1976 "Best pop vocal Performance by a Duo, Group or Chorus", at the 19th Annual Grammy Awards held on February 19, 1977; lucky for Chicago because it was a last minute inclusion on the disc.
Chicago XI (1977), included Cetera's ballad Baby, What a Big Surprise, a track that received a 4 US; the group's last top 10 hit of the decade.
Guercio left in 1978. January 23 of that same year, Kath died of an accidental, self-inflicted gunshot wound from a gun he thought was unloaded. Donnie Dacus was his replacement. Hot Streets (1978) followed. The lead-off single, Alive Again, brought Chicago back to the Top 15. It was their first album with a title rather than a number; and was Chicago's first LP to have a picture of the group; they would return to using numbers on subsequent releases but more would feature Arabic numerals instead of Roman. The album peaked at 12 on the Billboard charts; it was their first release since their debut to fail to make the Top 10. The album also marked a move away from the jazz-rock direction towards more pop songs and ballads. Chicago 13 followed in 1979.
Chicago XIV (1980), relegated the horn section to the background. Nonetheless, and the album's two singles failed to make Top 40.
Chris Pinnick joined Chicago to take up the guitar through to 1985. Sax player Marty Grebb joined on the subsequent tour.
The following year, 'Columbia Records' dropped them, believing them to no longer be of commercial benefit, but not before releasing a second "Greatest Hits" volume (unofficially known as Chicago XV) later that year to fulfill its contractual obligation. 'Warner Brothers' would now move in to take over the publishing role.
Keyboardist, guitarist, and singer Bill Champlin (of Sons of Champlin) would join. Laudir de Oliveira and Marty Grebb left.
For the 1982 follow-up album, Chicago 16 studio musicians were used for some tracks, along with new technology (such as synthesizers) that further reduced the horns section. The finally returned to the charts, however, with the Cetera-sung ballad Hard to Say I'm Sorry/Get Away.
1984's Chicago 17 became the biggest selling album of the band's history by allowing two more top ten (both 3) singles, You're the Inspiration and Hard Habit to Break. The album yielded two other hits Stay the Night (at 16) and Along Comes a Woman (14). Peter Cetera's brother, Kenny Cetera, was brought into the group for the supporting tour to augment percussion and add high harmony vocals.
1985 saw Chicago release their first music videos; that being for four songs as well as the track Good for Nothing on the famous 1985 We Are the World album.
Peter Cetera, meanwhile, had begun a solo career. He approached the band on the idea they would take breaks after tours to let him work on his solo work, but the band, not surprisingly, declined as so he left in the summer of 1985. On his own, he soon after felt success with Glory of Love (the theme song for The Karate Kid Part II), and with The Next Time I Fall (a duet with Amy Grant).
Chicago 18 (1986) saw the band fill Pinnick's role with session guitarists, none of whom became band members. The album included the 3 charting single Will You Still Love Me?, and the Top 20 pop song If She Would Have Been Faithful.... The album also featured an updated version of 25 or 6 to 4 that included a video. After the album release, Dawayne Bailey (ex-Bob Seger's Silver Bullet Band; guitar) would join.
Chicago 19 (1988) yielded several more top 10 hits, as well as Look Away, a track that was named as the Billboard Hot 100 No. 1 Song of the Year for 1989. The greatest hits album, Greatest Hits 1982-1989 followed in 1989.
In 1990 Danny Seraphine was fired, Tris Imboden (ex-Kenny Loggins and Peter Cetera; drums) replaced him an made his debut on the Twenty 1 release of 1991. The album survived an eleven-week stretch on Billboard, peaking at 66. The track Chasin' the Wind peaked at 39. The album made another 'record' so to speak as it would be their last featuring new original music for the next fifteen years. The reason: reorganization at the record label 'Reprise' (now a part of 'Warner') saw the album rejected and remain unpublished for fifteen years, aside from bootleg tapes and Internet files. This contributed to the parting of Chicago from the record label, speculation was a dispute over royalties for the back catalog. The album eventually saw the light of day in 2008 on 'Rhino Records' to receive a 122 on Billboard.
Chicago was recognized with a star on the Hollywood Walk of Fame on July 23, 1992.
1994 saw the departure of guitarist Dawayne Bailey.
After their 1994 tour and after signing with the 'Warner Bros. Records' imprint 'Giant Records', their next album, Night & Day: Big Band (1995), consisted of covers of songs recorded by Sarah Vaughan, Glenn Miller, and Duke Ellington.
Chicago XXV: The Christmas Album (1998) and the live album, Chicago XXVI (1999), followed.
In 2000, Chicago licensed the remaining of their entire catalog to 'Rhino Records' who returned the favor by releasing the two-disc compilation, The Very Best of Chicago: Only The Beginning (2000), that gave them a top 40 and sold some 2 million copies in the US alone. The label then released remastered versions of all of the band's 'Columbia'-era albums.
Chicago XXX (2006) was the first album in fifteen years to feature new material and it gave them a chart placing of 41 for their reward.
The Best of Chicago: 40th Anniversary Edition (Chicago XXXI) (2007) was another greatest hits album spanning their 40 year career to that point.
In 2008, "Stone of Sisyphus" (a.k.a. the aborted "Chicago XXII") was now officially released as Chicago XXXII in an expanded format.
Drew Hester joined the band in January 2009 to temporarily fill in for Imboden who was sick. In August 2009, Champlin was dismissed; keyboardist Lou Pardini replaced him.
The Christmas album Chicago XXXIII: O Christmas Three followed in 2011 with Chicago XXXIV: Live in '75 following later that year; the second album being a two-disc set featuring two hours of previously unreleased performances recorded June 24-26, 1975 at the Capital Centre in Largo, Maryland.
Hester then left the group to be succeeded by Daniel de los Reyes (percussions), then by Daniel's brother Walfredo Reyes Jr. (ex-Santana).
The albums Chicago XXXV: The Nashville Sessions (2013) and Chicago XXXVI: Now (2014) followed.
In 2015, Chicago received induction into the rock and Roll Hall of Fame. In February 2016, former drummer Danny Seraphine would join the current lineup for the first time in 25 years for that Induction Ceremony.
After taking a temporary leave in May 2016, citing "family health reasons", Jason Scheff left; Jeff Coffey, who had been filling in for Scheff, was promoted as a full-time member to replace him.