• Tour code: 26564P2
  • Location: Chicago, Illinois
  • Duration: 2 hours 30 minutes (approx.)
From USD $ 123.00 View price calendar

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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.


  • Historic Chicago sightseeing tour of the 1920s-1940s
  • Learn about the mafia, blues music, scandals and more
  • Explore the current nightlife scene in Chicago
  • Private guide ensures personal attention

What You Can Expect

Private Chicago Mafia and Blues Evening Tour

Discover Chicago's seedy and thrilling past

Begin this exploration into Chicago’s notorious past with a visit to the very location of the St. Valentine's Day Massacre — located in a garage on the city’s North Side — and find out about the events that led up to it. Then learn about Prohibition — including its history and how it became one of Chicago's defining moments. And see how the music known as ‘the Blues’ became a powerful force that helped the Mafia grow in Chicago.

Next, explore Chicago’s modern-day nightlife scene, featuring a stop at a legendary landmark bar that was previously owned by famous gangster Al Capone. Enjoy a drink (for a fee) and maybe some live music, in the spirit of the 1920s. Visitors must be at least 21 of age or older to enter. Please bring proper photo identification.

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