During the 1920s Prohibition Era, there were a number of Italian-American gangs that began smuggling in alcohol, bribing police, money laundering and getting involved in illicit activities revolving around the banned sale of alcohol as well as ... 

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Tours & Tickets

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Chicago Crime and Mob Tour, Chicago, null
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Chicago Crime and Mob Tour

4.5 star rating: Recommended 494 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 $35.95
$39.95 Save $4.00
Chicago Prohibition Tour, Chicago, Historical & Heritage Tours
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Chicago Prohibition Tour

5 star rating: Highly Recommended 100 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 $44.99
Historic Chicago Walking Bar Tour, Chicago, Bar, Club & Pub Tours
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Historic Chicago Walking Bar Tour

4.5 star rating: Recommended 30 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 Barrel Bus Prohibition Themed Gangster Tour, Chicago, Walking Tours
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Chicago Barrel Bus Prohibition Themed Gangster Tour

4.5 star rating: Recommended 8 Reviews

Take a 2-hour barrel bus adventure through the historic streets of Chicago on our Gangster Tour. Experience the rich chronicles of Chicagoland’s most ...  Read more

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

From USD $35.00
Chicago Barrel Bus Craft Brewery Tour, Chicago, Historical & Heritage Tours
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Chicago Barrel Bus Craft Brewery Tour

5 star rating: Highly Recommended 4 Reviews

The resurgence of craft beer is upon us! As you’re guided on this all-inclusive tour by our Prohibition-era experts to taste samples at three breweries ...  Read more

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

From USD $65.00
Chicago Southside Gangster Bicycle Tour, Chicago, Beer & Brewery Tours
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Chicago Southside Gangster Bicycle Tour

5 star rating: Highly Recommended 2 Reviews

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 $60.25
Chicago Gangster Tour, Chicago, Bike & Mountain Bike Tours
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Chicago Gangster Tour

1 star rating: I do not recommend this 4 Reviews

Chicago has a long history of organized crime and was famously home to the American mafia figure Al Capone. In 1850, Chicago had a population of 80,000 people, ...  Read more

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

From USD $35.00
Chicago Mafia and Blues Night Tour, Chicago, Historical & Heritage Tours
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Chicago Mafia and Blues Night Tour

Be prepared to time travel to an era between the 1920 and 1940's, and learn about mafia, blues, scandals, sports, and the current nightlife in Chicago.

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

From USD $123.00
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