Mafia and Prohibition Tours in Chicago

The Prohibition Era was a colorful time in the "The Windy City" with mobs and gangs running rampant—everyone from Al Capone to John Dillinger—and plenty of speakeasies where the liquor flowed. Here are the options to learn more about the era on a gangster tour of the city.

Mafia and Prohibition History in Chicago
See the spots once ruled by liquor, jazz, and the mafia on a Prohibition history tour. Visit relevant sites such as the Holy Name Cathedral, Biograph Theatre, Clark Street Bridge, and the site of the St. Valentine’s Day Massacre in 1929. Private tours include a Chicago nightlife option and a Chicago blues and Jazz Age history option.

Speakeasy & Cocktail Tours 
Another way to experience the city’s Prohibition era is to visit the pubs and bars that defied the 10-year alcohol ban. Speakeasy bars across the Old Town district, Wicker Park, and the Chicago Loop come to life on cocktail-themed tours.

Crime and Gangsters Tours
Learn about the Chicago crime of the past and take a trip back in time to the 1920s, ‘30s, and ‘40s on a crime and gangster tour. Hear stories about the iconic murders and crime scenes from this infamous time in the city's history. Explore Chicago's North Side, Lincoln Park, Gold Coast, Magnificent Mile, and other neighborhoods that are part of the city's gangster past.
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