In Old Chicago

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 Jack's Office

Russell Hicks

Politician in Jack's Office

Brooks Benedict

Courtroom Spectator (uncredited)

George Chandler

Onlooker (uncredited)

Bess Flowers

Woman with Colby (uncredited)

Vera Lewis

Wedding Witness (uncredited)

Bert Moorhouse

Opening Night Guest (uncredited)

William H. O'Brien

Senate Waiter (uncredited)

Martin Turner

Refugee