In Old Chicago Cast and Crew
 Tyrone Power - (Dion O'Leary) |
| Alice Faye - (Belle Fawcett) |
| Don Ameche - (Jack O'Leary) |
| Alice Brady - (Molly O'Leary) |
| Andy Devine - (Pickle Bixby) |
| Phyllis Brooks - (Ann Colby) |
| Brian Donlevy - (Gil Warren) |
| Tom Brown - (Bob O'Leary) |
| Sidney Blackmer - (Gen. Phil Sheridan) |
| Berton Churchill - (Senator Colby) |
| June Storey - (Gretchen O'Leary) |
| Paul Hurst - (Mitch) |
| Tyler Brooke - (Specialty Singer) |
| J. Anthony Hughes - (Patrick O'Leary) |
| Gene Reynolds - (Dion O'Leary (younger)) |
| Bobs Watson - (Bob O'Leary (younger)) |
| Billy Watson - (Jack as a Boy) |
| Spencer Charters - (Beavers) |
| Rondo Hatton - (Rondo, Bodyguard) |
| Ruth Gillette - (Miss Lou) |
| Eddie Collins - (Drunk) |
| Scotty Mattraw - (Beef King) |
| Charles Lane - (Booking Agent) |
| Frank Dae - (Judge) |
| Harry Stubbs - (Fire Commissioner) |
| Joe King - (Ship's Captain) |
| Francis Ford - (Driver) |
| Robert Murphy - (Police Officer) |
| Wade Boteler - (Police Officer) |
| Gustav von Seyffertitz - (Man in Jack's Office) |
| Russell Hicks - (Man in Jack's Office) |
| Harry Hayden - (Johnson, Secretary) |
| Vera Lewis - (Witness) |
| Mme. Sul Te Wan - (Hattie) |
| Minerva Urecal - (Frantic Mother) |
| Billy Watson - (Jack O'Leary (younger)) |
| Clarence H. Wilson - (Lawyer) |
| Ed Brady - (Wagon Driver) |
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