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
  • Greg T
    December 2017

    We loved this tour, giving us the opportunity to visit 4 different venues all unique with their own background and stories. So good to see them all still running today, each place was very busy.
    Our guide was very knowledgeable and informative, sharing history and answering questions along the way.
    Was great to see the variety of venues and enjoy with time for a couple of drinks at each place, some ofvtheparticipantscalsonhadvtime to order yummy food. We met some great people on the tour, from all over the world .
    The meeting place The Green Door was easy to find ,we walked from our hotel, the hidden tunnels, back rooms andcsecret passageways were very cool and the stories were fascinating.
    We discovered the Moscow Mule and have been enjoying this drink ever since back home , a great reminder of an awesome tour.
    At the end of the tour in the city last stop was a busy bustling restaurant that serves AMAZING pizza pie , so we stayed there for tea , this stop was central and easy to walk back to our hotel, or near the train and bus stop if needed.
    We loved the two stops in the middle as they were out of the city and in suburbia, our guide also explained these areas, and we loved seeing these areas of Chicago , so an additional bonus.
    Overall this was very well organised, interesting and lots of fun , have encouraged others to do this tour , they have and loved it as well :-
    Happy travels people !!
    Cheers from Australia

  • Marilyn M
    November 2017

    Fantastic tour

  • Sharon M
    November 2017

    We enjoyed this tour so much. It is essentially a drinking tour with history thrown in. It starts at The Green Door Tavern which is a great drinking hole with a speakeasy in the basement. Food is good there and we ate before the tour started. The guide was very knowledgable with the prohibition history, and the speakeasy in the basement is awesome. The other bars were good and the history given to us on the bus between them was so good - you got a feel for old time Chicago. cant reccommend this tour enough - if you love the idea of a little Chicago history and a lot of drinking - then this is the one for you - enjoy

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
  • Tour is not wheelchair accessible
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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