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
  • Misa A
    October 2017

    The tour guide was funny and very knowledgeable.

  • Kathryn P
    October 2017

    Great tour of 4 different prohibition era bars/restaurants. A really great way to see different parts of the city and learn LOTS of history and insights to cause and effects of prohibition all while tasting some amazing cocktails. Thoroughly enjoyed the evening.

  • Woodsy
    September 2017

    Hi, we booked the tour prior to travelling to Chicago. The tour was excellent ! The host Sydney Back was a real character and very knowledgeable. The tour took in a number of speakeasy bars, which included beverages at each site. We were all very jolly by the end of the tour. If you are interested in history with a gangster edge, then this is the tour fo you. Highly recommended !

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
  • Hotel pickup and drop-off
Additional Info
  • Confirmation will be received at time of booking
  • Minimum age is 21 years
Schedule and Pricing
Departure Point

The Green Door Tavern

Departure Time and Comments

4pm /


3 hours 30 minutes

Return Details

Concludes at Exchequer Pub

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