In Old Chicago (1938) is a Drama, History film that follows the O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire. Currently, you can watch In Old Chicago on Amazon Video, Apple TV Store, Google Play Movies, YouTube. Streaming availability may vary by country and platform over time. It has a user rating of 6.7 out of 10 from 49 votes. Fans of drama movies may also want to explore similar titles below.