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Chicago RECOMMENDATIONS See all

Mafia and Prohibition Tours in Chicago

By Viator, January 2018

4.5 43 Reviews | Add your review

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.

Tours & Tickets

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Chicago Prohibition Tour, Chicago, null
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Chicago Prohibition Tour

5 star rating: Highly Recommended 107 Reviews

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes (approx.)

From USD $45.00
Chicago Crime and Mob Tour, Chicago, Bar, Club & Pub Tours
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Chicago Crime and Mob Tour

4.5 star rating: Recommended 374 Reviews

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes (approx.)

From USD $39.95
Historic Chicago Walking Bar Tour, Chicago, Historical & Heritage Tours
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Historic Chicago Walking Bar Tour

4.5 star rating: Recommended 27 Reviews

Explore downtown Chicago on a pub crawl with an educational twist! Your expert guide shares entertaining facts about the history of jazz, theater, social ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes (approx.)

From USD $38.00
Chicago Craft Brewery Barrel Bus Tour, Chicago, Walking Tours
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Chicago Craft Brewery Barrel Bus Tour

5 star rating: Highly Recommended 3 Reviews

There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is the perfect ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes (approx.)

From USD $78.40
Chicago Barrel Bus Craft Distillery Tour, Chicago, Beer & Brewery Tours
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Chicago Barrel Bus Craft Distillery Tour

Indulge in some of Chicago’s uniquely crafted spirits on this all-inclusive distillery tour. Have samples at three local distilleries and tour one distilling ...  Read more

Location: Chicago, Illinois
Duration: 4 hours (approx.)

From USD $78.40
Old Chicago Gangster Electric Bike Tour, Chicago, Distillery Tours
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Old Chicago Gangster Electric Bike Tour

5 star rating: Highly Recommended 1 Review

Travel back in time to the seamier side of Chicago on this guided bicycle tour that takes you to the Southside hangouts of notorious Chicago gangsters like Al ...  Read more

Location: Chicago, Illinois
Duration: 4 hours (approx.)

From USD $63.85
Private Chicago Mafia and Blues Evening Tour, Chicago, Bike & Mountain Bike Tours
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Private Chicago Mafia and Blues Evening Tour

It isn’t Chicago history without a dose of mafia intrigue — and some killer blues tunes, too. This lively and fascinating private tour sends you back to the ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes (approx.)

From USD $123.00

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