Modern engineering meets 1920s history in our Gangster Tours. Experience the rich chronicles of Chicagoland’s most infamous figures and meet some of the little-known working class innovators who made this city the center of the underground struggle against Prohibition.  Our guides will take you to locations where mobsters practiced their outlawed trades while educating you on history of the Jazz Age that defined Chicago for generations.

Step on the unique barrel bus through the speakeasy style vertical door to start your one of a kind Prohibition themed Gangster tour. As you are driven through the historic streets of Chicago on a climate controlled and comfortable ride, learn about the notorious members of the north, south, and west side gangs that existed during the Prohibition-era. Your guide provides an entertaining insight as to the struggles that mobsters and bank robbers faced in a time when alcohol was prohibited.

Pass by and learn about multiple locations including the Saint Valentine’s Day Massacre site, Union Station, Board of Trade, The Rookery, and City Hall. Step outside at the Holy Name Cathedral and Biograph Theater to relive historic occurrences that define the locations for generations. Hear stories about Al Capone, John Dillinger, Bugs Moran, Johnny Torrio, George Remus, and more. Enjoy period era correct music and a couple of games that truly make your entire tour feel like a step back in time.

Tour Duration: Approximately 2hrs

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Pickup/Dropoff Location: 600 N Clark St, Chicago, IL 60610


Tour Details
Locales Visited

Al Capone’s Hideouts
Holy Name Cathedral
Biograph Theater – Dillinger Assassination
Saint Valentine’s Day Massacre
Union Station
City Hall
Courthouse Place

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