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In Old Chicago

6.719381h 51mNRMovieDramaHistory

The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire.

DirectorHenry King
WritersLamar Trotti·Niven Busch
ProducerDarryl F. Zanuck

Where to watch

Availability shown for Canada · rights vary by country

Cast · Directed by Henry King

TPTyrone Power
Tyrone Power
Dion O'Leary
AFAlice Faye
Alice Faye
Belle Fawcett
DADon Ameche
Don Ameche
Jack O'Leary
ABAlice Brady
Alice Brady
Molly O'Leary
ADAndy Devine
Andy Devine
Pickle Bixby
BDBrian Donlevy
Brian Donlevy
Gil Warren
PBPhyllis Brooks
Phyllis Brooks
Ann Colby
TBTom Brown
Tom Brown
Bob O'Leary
SBSidney Blackmer
Sidney Blackmer
General Phil Sheridan
BCBerton Churchill
Berton Churchill
Senator Colby
JSJune Storey
June Storey
Gretchen
PH
Paul Hurst
Mitch

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More from Alice Faye · Co-star actress

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More from Henry King · Director

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In Old Chicago — streaming FAQ

Which OTT platform streams In Old Chicago?

In Old Chicago isn't on any subscription service in Canada right now, but you can rent or buy it on YouTube and Amazon Video. It's not on Netflix.

Is In Old Chicago on Netflix?

No, In Old Chicago is not on Netflix in Canada as of November 2026. You can rent or buy it on YouTube and Amazon Video.

Is In Old Chicago on Amazon Prime Video?

In Old Chicago isn't included with a Prime Video subscription in Canada, but you can rent or buy it on Amazon Video.

Where can I watch In Old Chicago for free?

In Old Chicago isn't available free in Canada; you can only rent or buy it on YouTube and Amazon Video.