![In Old Chicago](https://image.tmdb.org/t/p/original//7ayKhcVQrvePAKfHMyghG0nbDHz.jpg)
![In Old Chicago](https://image.tmdb.org/t/p/w200//s3DPtiEGx4thHOGcIjdgBlWp8D0.jpg)
In Old Chicago
1 hour 51 minutes1938-04-15
6.4
Watch Trailer
The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire.
Cast
![Tyrone Power](https://image.tmdb.org/t/p/w200//sHiIUmasHuY8avM3yasQsL3wSKm.jpg)
Tyrone Power
Dion O'Leary
![Alice Faye](https://image.tmdb.org/t/p/w200//jC15KAoPnRWuuGWP2msKxWZsa3I.jpg)
Alice Faye
Belle Fawcett
![Don Ameche](https://image.tmdb.org/t/p/w200//p2Q0LE3SECDvb5W2yAvvfRtzIyo.jpg)
Don Ameche
Jack O'Leary
![Alice Brady](https://image.tmdb.org/t/p/w200//v9XVx9jV7ntUKog525jrYkSnq3n.jpg)
Alice Brady
Molly O'Leary
![Andy Devine](https://image.tmdb.org/t/p/w200//rBCv7cszfbo2dkQbGxxff9xTppL.jpg)
Andy Devine
Pickle Bixby
![Brian Donlevy](https://image.tmdb.org/t/p/w200//1ScpU7sf6WGlWhHqc0EYlfA4L1d.jpg)
Brian Donlevy
Gil Warren
![Phyllis Brooks](https://image.tmdb.org/t/p/w200//vh9zftnknwkiGppOOUhBrosQQvM.jpg)
Phyllis Brooks
Ann Colby
![Tom Brown](https://image.tmdb.org/t/p/w200//ehCgDrUhMQA7gBL7fm7kBoK8jQO.jpg)
Tom Brown
Bob O'Leary
![Sidney Blackmer](https://image.tmdb.org/t/p/w200//2JzR0u8yvrkp3e0GB5cajCqGDjp.jpg)
Sidney Blackmer
General Phil Sheridan
![Berton Churchill](https://image.tmdb.org/t/p/w200//xBJ2nc9DMFRLlyxhRXCymsGj9Y5.jpg)
Berton Churchill
Senator Colby
![June Storey](https://image.tmdb.org/t/p/w200//nckAZ4ErJHv3LgcPfmxPngoMUi.jpg)
June Storey
Gretchen
![Paul Hurst](https://image.tmdb.org/t/p/w200//l068yW6ly6M7IkjTWD8qtB5O2kA.jpg)
Paul Hurst
Mitch
![Tyler Brooke](https://image.tmdb.org/t/p/w200//aByPm4kWcdSWwGdXjBmcPipdSp2.jpg)
Tyler Brooke
Specialty Singer
![J. Anthony Hughes](https://image.tmdb.org/t/p/w200//5ZSV8eKiU4BDcRy1nU2MDnq4a4c.jpg)
J. Anthony Hughes
Pat O'Leary
![Gene Reynolds](https://image.tmdb.org/t/p/w200//6yDAz8JMGw04ndeFhAxb1NR4OqC.jpg)
Gene Reynolds
Dion O'Leary (as a boy)
![Bobs Watson](https://image.tmdb.org/t/p/w200//1L62x1ZNs1gwECeKPmF6I0Tkv8K.jpg)
Bobs Watson
Bob O'Leary (as a boy)
![Billy Watson](/_next/static/media/notFound.aecd17f8.png)
Billy Watson
Jack O'Leary (as a boy)
![Madame Sul-Te-Wan](https://image.tmdb.org/t/p/w200//h8o5CowohYMNE3USzyWKN0CgwFv.jpg)
Madame Sul-Te-Wan
Hattie
![Spencer Charters](https://image.tmdb.org/t/p/w200//mIx8iHZIGcGbB1hP80RV4vxBcrd.jpg)
Spencer Charters
Commissioner W.J. Beavers
![Rondo Hatton](https://image.tmdb.org/t/p/w200//zFP3fGUQuPgvu3AJZOHsscV45KU.jpg)
Rondo Hatton
Rondo - Body Guard
![Thelma Manning](/_next/static/media/notFound.aecd17f8.png)
Thelma Manning
Carrie Donahue
![Ruth Gillette](https://image.tmdb.org/t/p/w200//xwOdT1c5Ms7wq2Nt5t2W7UH5GI0.jpg)
Ruth Gillette
Miss Lou
![Eddie Collins](https://image.tmdb.org/t/p/w200//wsXhLs3kW58JDkzC6UVvy1zT0vQ.jpg)
Eddie Collins
Drunk
![Scotty Mattraw](/_next/static/media/notFound.aecd17f8.png)
Scotty Mattraw
Beef King
![Joe Twerp](/_next/static/media/notFound.aecd17f8.png)
Joe Twerp
Stuttering Clerk
![Clarence Wilson](https://image.tmdb.org/t/p/w200//zi37Pkxd7IsNFjgdbbkK8apgtmr.jpg)
Clarence Wilson
Lawyer
![Frank Dae](https://image.tmdb.org/t/p/w200//wHwOtv12HzgffdCdz58yJQniWZ4.jpg)
Frank Dae
Judge
![Harry Stubbs](https://image.tmdb.org/t/p/w200//9w8e41q6hzBIMss8EQvtaIPOSmV.jpg)
Harry Stubbs
Fire Commissioner
![Joe King](https://image.tmdb.org/t/p/w200//wCQK5tVurkQL00FeDwW6nh3viLn.jpg)
Joe King
Ship's Captain
![Francis Ford](https://image.tmdb.org/t/p/w200//v5MKJZbr5kwP7KbLjNgw7Bqwsto.jpg)
Francis Ford
Driver
![Bob Murphy](/_next/static/media/notFound.aecd17f8.png)
Bob Murphy
Police Officer
![Wade Boteler](https://image.tmdb.org/t/p/w200//mPvA7aaDLlMl1qksm1z8KRsDZyV.jpg)
Wade Boteler
Police Officer
![Gustav von Seyffertitz](https://image.tmdb.org/t/p/w200//849KvertinEPsW09lOgXAza44F2.jpg)
Gustav von Seyffertitz
Dutch - Politician in Jack's Office
![Russell Hicks](https://image.tmdb.org/t/p/w200//5Pir7aPr3Iooqd8eYhHLlJWicZa.jpg)
Russell Hicks
Politician in Jack's Office
![Brooks Benedict](https://image.tmdb.org/t/p/w200//l3Bw5oBij94yG0QSO45inFnySRZ.jpg)
Brooks Benedict
Courtroom Spectator (uncredited)
![George Chandler](https://image.tmdb.org/t/p/w200//fXj6FdgWPp8om9O2HD2Uv4yhcBi.jpg)
George Chandler
Onlooker (uncredited)
![Bess Flowers](https://image.tmdb.org/t/p/w200//bTeLHYMnODJNJnlbkH0QXI87cDF.jpg)
Bess Flowers
Woman with Colby (uncredited)
![Vera Lewis](https://image.tmdb.org/t/p/w200//2mKt5b7EAPEjvRFbUHzTD8oGoxV.jpg)
Vera Lewis
Wedding Witness (uncredited)
![Bert Moorhouse](/_next/static/media/notFound.aecd17f8.png)
Bert Moorhouse
Opening Night Guest (uncredited)
![William H. O'Brien](https://image.tmdb.org/t/p/w200//dHqtM4SNmq6W2WBnxyXgRdlgSfk.jpg)