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Chicago Prohibition Tour

24 Reviews
  • Product Details
  • Reviews
  • Important Information

Meet your guide at the Green Door Tavern to start the 3.5-hour journey to four historic Chicago speakeasies used during Prohibition that still operate today. Bring your government-issued ID, money to purchase drinks, and a camera for photo ops.

Travel by comfortable air-conditioned coach between stops, and learn about the 1920s cocktails typically found in each establishment. If you like what you see and hear, purchase signature drinks to taste for yourself. As you sip craft cocktails made by expert bartenders, your enthusiastic and knowledgeable guide explains the key players of Prohibition. Hear stories about the lawmakers and the lawbreakers, including Al Capone and other famous Chicago gangsters who became powerful during the dry years of Prohibition.

Each former speakeasy that you visit has a different character. Stops include a downtown tavern built in 1872 that is decorated with antiques and Americana collectibles that give it an old-school Chicago vibe. Then pull up a stool at a cocktail lounge in Wicker Park where great blues music pumps from an old jukebox. You'll also enjoy a neighborhood bar that claims to be the oldest and longest-running tavern in the Old Town district. Wrap up at a downtown restaurant rumored to be a favorite hangout of Al Capone where historic newspapers, photographs, and posters line the walls of the bar.

Your tour ends downtown in the Chicago Loop.

  • Informative, friendly and professional guide
  • Step back in time on a history tour
  • Comprehensive tour of the city
Customer Reviews
  • jrieck31
    August 2018

    Sidney is probably the most entertaining tour guide I've ever had. Lots of laughs, good drinks, and learned some stuff to boot. Highly recommend.

  • Rebecca K
    August 2018

    We had Sydney as a guide, and she was fantastic. She knows her history, she was fun, and the tour was great.

  • Jill F
    July 2018

    This is fun tour --education and cocktails! Definitely for adults with a sense of humor only as some of the presentation is

Product Details
  • Transport by air-conditioned coach
  • Live commentary on board
  • Professional guide
  • Printed guide to follow along with drink recommendations.
  • Gratuities (optional)
  • Food and drinks (available for purchase)
  • Hotel pickup and drop-off
Additional Info
  • Confirmation will be received at time of booking
  • Minimum age is 21 years
  • Tour is not wheelchair accessible
Schedule and Pricing
Departure Point

Harry Caray’s

Departure Time and Comments

4pm /


3 hours 30 minutes

Return Details

Concludes at Exchequer Pub

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