Chicago (band) award received star on Hollywood Walk of Fame
1990s: more changes and Stone of Sisyphus
The beginning of the 1990s brought yet another departure. Original drummer Danny Seraphine was dismissed from the band in May 1990. Seraphine was succeeded by Tris Imboden, a longtime drummer with Kenny Loggins and former session drummer with Peter Cetera. 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, 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.In 1993, Chicago wrote and recorded their 22nd album Stone of Sisyphus. This album was to have marked their return to their traditional composition of the 1970s, emphasizing major horn accompaniment. 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 It remained unpublished for fifteen years, aside from bootleg tapes and Internet files. 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. The album eventually saw an expanded release on Rhino Records in June 2008 to favorable reviews from both fans and critics and made it to No. 122 on the album charts.After finishing their 1994 tour, and after signing with the Warner Bros. Records imprint label Giant Records, they released their 1995 album Night & Day: Big Band, 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. The album featured guest appearances by Paul Shaffer of Late Show with David Letterman fame, Aerosmith guitarist Joe Perry, and The Gipsy Kings. 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. After this big band album, Chicago acquired the rights to their Columbia recordings and reissued them on their own imprint. 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.In 1998, Chicago released Chicago XXV: The Christmas Album and a live album in 1999, Chicago XXVI on their own imprint.1970: Best Album of 1970: Chicago, Cash Box
1976: City of Chicago Medal of Merit (city's highest civilian award)
1976: Awarded a Cartier 25-pound bar of pure platinum by Columbia Records for platinum album achievement.
1977: Madison Square Garden "Gold Ticket Award" for drawing over 100,000 people to the venue over the years.
1987: American Video Award, Best Cinematography, "25 or 6 to 4" (Bobby Byrne)
1992: Hollywood Walk of Fame star for music contributions, located at 6400 Hollywood Boulevard
2016: Rock and Roll Hall of Fame induction (original members: Cetera, Kath, Lamm, Loughnane, Pankow, Parazaider, Seraphine) 
2017: Songwriters Hall of Fame: James Pankow and Robert Lamm (inducted), Peter Cetera (elected, not inducted)
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