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Chicago gangster & mob tours: Capone, Prohibition and the Outfit

Quick answer: a Chicago gangster tour takes you through the world of Al Capone and the Chicago Outfit — Prohibition bootlegging, the gang wars, the speakeasies and the site of the St. Valentine’s Day Massacre. Choose a walking tour downtown, a wider-ranging mob bus or luxury minibus tour, or a speakeasy-themed trip — with private options for groups.
The story you’ll follow
Between 1920 and 1933, Prohibition turned Chicago into the capital of organized crime. Al Capone’s Outfit ran the bootlegging, the gambling and the speakeasies, and settled scores in the streets — most infamously the 1929 St. Valentine’s Day Massacre. A gangster tour maps that era onto the modern city, from old hideouts to the spots where it all went down.
Gangster & mob tours
Mob & crime
Best sellerChicago Gangsters & Ghosts Guided Walking Tour
★ 4.7 · 1,765 reviews
from $30 / person
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Go deeper
Read about Al Capone’s Chicago, the St. Valentine’s Day Massacre, and Prohibition & speakeasies.