For years, if you wanted a comprehensive Chicago hits collection, your choices were slim. 1975's single-disc/eleven-track collection, Greatest Hits (Chicago IX) remained your best bet, but it only included tracks from the group's beginning to the mid-'70s (without question their best years). On the other hand, if it was Chicago's power ballad direction of the '80s you were after, your only choice was 1989's Greatest Hits: 1982-1989.

Chicago XIV is the twelfth studio album by the American band Chicago, released in 1980. Recorded at a time of waning interest in the band, Chicago XIV remains one of Chicago's poorest selling albums and was a commercial flop. It is also notable for being their last studio album with Columbia Records.

Chicago X is the eighth studio album, and tenth album overall, by the American band Chicago and was released on June 14, 1976. The album is notable for its soulfulness, and it ended up being a turning point in the band's career thanks to one song.

A 2017 stereo version of Chicago II, an album that still sounds like nothing else. Originally issued in 1970, Chicago's second album brims with confidence and inspiration as it draws on everything from ambitious orchestral music to heavy rock. Chicago II has been remixed before, but never like this. For the first time, a stereo remix from the 16-track multi-track tapes made it possible for Steven Wilson to bring out elements that were muffled or submerged in the mix. The result is a stereo version of Chicago II that boasts a clarity and punch it didn't possess before

Chicago 16 is the thirteenth studio album by the American band Chicago, released on June 7, 1982. It is the first album in a decade-long association with new label Warner Bros. Records; the band's first project to be produced by David Foster; and their first hit album since 1978's Hot Streets. It is also the first album since Chicago V (1972) not to feature Laudir de Oliveira on percussions.

Twenty 1 is the seventeenth studio album (and twenty-first overall) by the American band Chicago. Released on January 29, 1991, it was their first album of the 1990s. Twenty 1 spent eleven weeks on the American Billboard 200, peaking at position #66, and did not chart in the UK.

"If You Leave Me Now" was also Chicago's biggest hit worldwide, topping the charts in other countries such as Australia. It won Grammy Awards for Best Arrangement Accompanying Vocalist(s) and Best Pop Vocal Performance by a Duo, Group or Chorus. In addition, by August 1978 it had sold 1.4 million copies in the United States alone.
The song had been featured in some several television series and movies such as Three Kings, Shaun of the Dead, A Lot Like Love, Sex and the City and the video game Grand Theft Auto V.

Chicago XXXVI: Now, sometimes stylized as "NOW" Chicago XXXVI, is the twenty-third studio album, and thirty-sixth overall by Chicago. It was written and recorded in 2013-2014, and was released on July 4, 2014. Aside from the sprinkling of new tracks found in the band's many compilation and cover albums, Now is the band's next full album of new compositions in the eight years since 2006's Chicago XXX, and it is the next release of original material following 2008's fifteen-year-delayed Chicago XXXII: Stone of Sisyphus. This album marks the first original Chicago credits for veteran musicians Walfredo Reyes, Jr. and Lou Pardini, since joining the band.

Chicago VI is the fifth studio album by American rock band Chicago and was released in 1973. Following the streamlined character of Chicago V, this successor would see the group follow more of a pop music approach, relying less on their trademark horns and exploring varied music forms.