The history of legendary rock band Chicago is chronicled from their inception in 1967 all the way to the present.
| Actor | Role |
|---|---|
 Lee LoughnaneSelf | Self |
 Robert LammSelf | Self |
 Walter ParazaiderSelf | Self |
 James PankowSelf | Self |
 Danny SeraphineSelf | Self |
| PPeter SchivarelliSelf | Self |
 Jason ScheffSelf | Self |
 David FosterSelf | Self |
 Keith HowlandSelf | Self |
| LLou PardiniSelf | Self |
| CChris PinnickSelf | Self |
| WWalfredo ReyesSelf | Self |
 Irving AzoffSelf | Self |
 Joe MantegnaSelf | Self |
| NNed CollettiSelf | Self |
 Clive DavisSelf | Self |
 Carlos AmezcuaSelf | Self |
| DDavid AmezcuaSelf | Self |
| LLarry FitzgeraldSelf | Self |
 Jimmy PardoSelf | Self |
| KKatherine MuiseSelf | Self |
 Tris ImbodenSelf | Self |
 Peter CeteraSelf (archive footage) | Self (archive footage) |
 Terry KathSelf (archive footage) | Self (archive footage) |
 James William GuercioSelf (archival footage) | Self (archival footage) |
| James William GuercioSelf (archive footage) | Self (archive footage) |
 Don DacusSelf (archive footage) | Self (archive footage) |
 Bill ChamplinSelf (archive footage) | Self (archive footage) |
| DDawayne BaileySelf (archive footage) | Self (archive footage) |
| JJohn HonoréTerry Kath | Terry Kath |