Greatest Hits 1982-1989 is the third greatest hits album by American rock band Chicago and released in 1989. Covering the era that stretched from 1982's Chicago 16 to Chicago 19 in 1988, the set is also balanced by the appearances of both Peter Cetera and his replacement Jason Scheff.

Greatest Hits 1982-1989 - the band's twentieth release overall - is also notable for being Chicago's last release before the departure of founding drummer Danny Seraphine and the home to a (slightly) remixed hit, "What Kind Of Man Would I Be?" originally released on Chicago 19.

Although it only reached #37 in the US, Greatest Hits 1982-1989 would go on to sell over six million units in the US alone.