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Mafia and Prohibition Tours in Chicago

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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4 Tours and Activities | All Chicago Tours

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Chicago Crime and Mob Tour

Chicago Crime and Mob Tour

star-4
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Chicago Craft Brewery Barrel Bus Tour

Chicago Craft Brewery Barrel Bus Tour

star-4.5
Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$89.60
From
$89.60
Taking safety measures

Chicago Barrel Bus Craft Distillery Tour

Chicago Barrel Bus Craft Distillery Tour

star-5
Learn about Chicago’s distillery scene and indulge in a variety of spirits on this guided, 4-hour tour. Visit three local distilleries for craft spirit samples — including whiskey, gin, apple brandy, vodka and more — plus an additional distilling production facility for an in-depth tour. Discover the science behind the distilling process, complete with step-by-step procedures, and enjoy approximately a dozen samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$89.60
From
$89.60
Taking safety measures

Private Chicago Mafia and Blues Evening Tour

Private Chicago Mafia and Blues Evening Tour

star-5
Travel back in time to learn about life in Chicago in the 1920s, 30s, and 40s on this private, 2.5-hour sightseeing tour. Learn about the mafia, blues music, plus the city’s scandals, sports teams, and more. Then explore the current nightlife scene in the Windy City.
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  • 2 hours 30 minutes
From
$220.00
Price varies by group size
From
$220.00
Price varies by group size