Chicago es, junto con Blood, Sweat & Tears (BS&T), la banda más representativa,1 y la más exitosa en términos comerciales,2 de lo que se dieron en llamar Big Bands de Rock. Se fundó en la ciudad de su mismo nombre, en 1967, aunque inicialmente se denominó "Chicago Transit Authority", nombre que debieron recortar por problemas jurídicos con la autoridad de transporte público de la ciudad. El grupo permanece activo en la actualidad.
| 1 | Old Days | Group Portrait |
| 2 | Ballet for a Girl in Buchannon: West Virginia Fant | Chicago II |
| 3 | Till We Meet Again | Chicago VIII |
| 4 | Ballet for a Girl in Buchannon: Now More Than Ever | Chicago II |
| 5 | Baby What A Big Surprise | Chicago XV - Chicago's Greatest Hits, Vol. II |
| 6 | Wishing You Were Here | Chicago Ix: Greatest Hits 69-74 |
| 7 | Hard To Say I'm Sorry | The Very Best of Chicago: Only the Beginning |
| 8 | The Road | Chicago II |
| 9 | What Kind Of Man Would I Be? | Chicago: Greatest Hits 1982-1989 |
| 10 | Ballet for a Girl in Buchannon: A.M. Mourning | Chicago II |
| 11 | Just You 'n' Me | The Very Best of Chicago: Only the Beginning |
| 12 | If It Were You | Twenty 1 |
| 13 | Saturday In The Park | If You Leave Me Now |
| 14 | Colour my world | Chicago: Greatest Hits |
| 15 | Ballet for a Girl in Buchannon: West Virginia Fant | Chicago II |
| 16 | Will You Still Love Me? | Chicago: Greatest Hits 1982-1989 |
| 17 | It Better End Soon: 3rd Movement | Chicago II |
| 18 | Hard To Say I'm Sorry - Get Away | Chicago: Greatest Hits 1982-1989 |
| 19 | Somebody, Somewhere | Twenty 1 |
| 20 | Harry Truman | Chicago VIII |