In Old Chicago The Great American Motion Picture! The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire. Details Casts Videos Galleries Posters Title In Old Chicago Release Date 1938-04-15 Runtime 01 Hours 51 Minutes Genres Drama History Production Companies Darryl F. Zanuck Productions, 20th Century Fox Production Countries United States of America Tyrone Power... Dion O'Leary... Alice Faye... Belle Fawcett... Don Ameche... Jack O'Leary... Alice Brady... Molly O'Leary... Andy Devine... Pickle Bixby... Brian Donlevy... Gil Warren... Phyllis Brooks... Ann Colby... Tom Brown... Bob O'Leary... Sidney Blackmer... General Phil Sheridan... Berton Churchill... Senator Colby... June Storey... Gretchen... Paul Hurst... Mitch... Tyler Brooke... Specialty Singer... J. Anthony Hughes... Pat O'Leary... Gene Reynolds... Dion O'Leary (as a boy)... Bobs Watson... Bob O'Leary (as a boy)... Billy Watson... Jack O'Leary (as a boy)... Madame Sul-Te-Wan... Hattie... Spencer Charters... Commissioner W.J. Beavers... Rondo Hatton... Rondo - Body Guard... Thelma Manning... Carrie Donahue... Ruth Gillette... Miss Lou... Eddie Collins... Drunk... Scotty Mattraw... Beef King... Joe Twerp... Stuttering Clerk... Clarence Wilson... Lawyer... Frank Dae... Judge... Harry Stubbs... Fire Commissioner... Joe King... Ship's Captain... Francis Ford... Driver... Bob Murphy... Police Officer... Wade Boteler... Police Officer... Gustav von Seyffertitz... Dutch - Politician in Jac... Russell Hicks... Politician in Jack's Offi... Brooks Benedict... Courtroom Spectator (uncr... George Chandler... Onlooker (uncredited)... Bess Flowers... Woman with Colby (uncredi... Vera Lewis... Wedding Witness (uncredit... Bert Moorhouse... Opening Night Guest (uncr... William H. O'Brien... Senate Waiter (uncredited... In Old Chicago 1937 Official Trailer (Nominated Oscar / Best Picture) (Trailer) Original Size (2635x1483) Original Size (1982x1115) Original Size (1280x720) Original Size (1400x2100) Original Size (1181x1772) Original Size (2000x3000) Original Size (1000x1500) Original Size (1892x2838) Original Size (1400x2100) Original Size (580x870) Original Size (600x900) Original Size (667x1000) Original Size (2000x3000) Original Size (2000x3000) Original Size (930x1303) Original Size (1877x2815) Original Size (1000x1500) Original Size (2000x3000) Original Size (960x1440) Original Size (1206x1809) Original Size (2000x2700) Original Size (500x750) Original Size (1000x1506) Original Size (1507x2175) Original Size (719x1000) Original Size (1000x1500) Original Size (1000x1500)