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.
Starring
Tyrone Power, Alice Faye, Don Ameche
Updated Feb 16, 2026
WHERE TO WATCH
Prime Video
3 countries
YouTube
2 countries
G
Google Play
2 countries
Apple TV
1 country
DROPTHE_ GOSSIP
Year context
In Old Chicago was released 88 years ago in 1938.
Overview
The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire.
In Old Chicago is a Drama, History film with a runtime of 1h 51m.
CAST (20)
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)
BW
Billy Watson
Jack O'Leary (as a boy)
Madame Sul-Te-Wan
Hattie
Spencer Charters
Commissioner W.J. Beavers
Rondo Hatton
Rondo - Body Guard
BOX OFFICE
$10.0M
Budget
DETAILS
Release
Status
Released
Runtime
111 min (1h 51m)
Country
Rating
6.6/10 (44 votes)
Budget
$10,000,000
FREQUENTLY ASKED QUESTIONS
What is In Old Chicago about?
The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire.
How long is In Old Chicago?
In Old Chicago has a runtime of 111 minutes (1h 51m).
Who stars in In Old Chicago?
The cast of In Old Chicago includes Tyrone Power, Alice Faye, Don Ameche, Alice Brady, Andy Devine.
What is the rating of In Old Chicago?
In Old Chicago has a rating of 6.6 out of 10 based on 44 votes on TMDB.
GENRES (2)
Drama
History