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 Prohibition Tour, Chicago, null
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Chicago Prohibition Tour

5 star rating: Highly Recommended 55 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
Chicago Crime and Mob Tour, Chicago, Bar, Club & Pub Tours
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Chicago Crime and Mob Tour

4.5 star rating: Recommended 277 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
Historic Chicago Walking Bar Tour, Chicago, Historical & Heritage Tours
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Historic Chicago Walking Bar Tour

5 star rating: Highly Recommended 18 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 2 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: 4 hours (approx.)

From USD $65.00
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 $65.00
Private Chicago Mafia and Blues Evening Tour, Chicago, Distillery 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
Chicago Gangster Tour, Chicago, City Tours
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Chicago Gangster Tour

1 star rating: I do not recommend this 2 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 Southside Gangster Bicycle Tour, Chicago, Historical & Heritage Tours
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Chicago Southside Gangster Bicycle 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
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