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Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.


  • Visit bars in the Old Town district, Wicker Park, and the Chicago Loop
  • Learn about cocktails that date to the 1920s
  • Enjoy a fun and informative historical tour led by an entertaining guide
  • Hear about the crime syndicates of Chicago’s most notorious scofflaws, including Al Capone
  • Understand the roots of the temperance movement that led to Prohibition and its consequences

Recent Photos of This Tour

What You Can Expect

Chicago Prohibition Tour

See antiques used during the prohibition era.era.

Start your 3.5-hour Chicago Prohibition tour at the Green Door Tavern — a vintage downtown bar built in 1872 and decorated with antiques and Americana collectibles that give it a sense of old-time Chicago. Be sure to bring along your government-issued ID and some cash to purchase craft cocktails and signature drinks made by expert bartenders on this adults-only tour.

Your entertaining guide illuminates the underground world of Chicago’s historic speakeasies used during Prohibition and still in operation today. Learn why the sale of alcohol was banned in the US from 1920 to 1933, and discover Prohibition’s key players. Hear anecdotes about lawbreakers like Al Capone and other Chicago mobsters who became powerful during the dry years.

A coach shuttles you between four establishments, each with a different character. 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 your Chicago speakeasy tour at Exchequer Pub, a Chicago Loop restaurant where historic photographs and posters line the walls of the decades-old bar.

Customer Reviews

Bill D United States of ... 

5 star rating: Highly Recommended November 2016

Who loves drinking and history???
Sydney does!
My wife and I took the tour last week and we couldn't have had a better time..
Sydney's knowledge and passion for Prohibition and history is exceeded only by her knowledge and passion for drinking!
She does so much more than rattling off facts... She is incredibly entertaining as well.... Quick-witted and fun.
Take the tour... You'll be happy you did.


5 star rating: Highly Recommended November 2016

We learned a lot about Prohibition years in Chicago and we visited bars we woul not have found on our own - this trip is great if you want to see some sights off the beaten track. Be prepared to get a taxi home as trip does not end were it picked up.

Deborah D

5 star rating: Highly Recommended October 2016

This tour was fun, run professionally, on time, and delivered what was expected. Would definitely recommend this tour, and would take it again.

Charlie J

5 star rating: Highly Recommended August 2016

Excellent tour guide who was incredibly knowledgeable and funny too. The bars were great too and we would never have found them otherwise! Good fun.

Karin F

5 star rating: Highly Recommended July 2016

Excellent guide with incredible knowledge and fine people funny!

Margaret Cerie O

5 star rating: Highly Recommended July 2016

This was an excellent tour. Our guide Jonathan was both funny and informative. He's the Ken Burns tour guide you always wanted. The locations are fascinating the drinks delicious especially the lemon drop martini at Club Lucky's. Highly recommend this loads of fun

Glenda H Australia

5 star rating: Highly Recommended June 2016

Had a lot of fun of this tour, our guide was excellent


5 star rating: Highly Recommended June 2016

Exceptional tour and our guide Sydney was terrific, her knowledge and passion for the subject truly made this a wonderful tour. The bars we visited and the drinks consumed were excellent. Thoroughly recommend this tour and next time we are in Chicago we will do it again.

Markus D

5 star rating: Highly Recommended June 2016

Awesome tour.
Awesome guide.
Awesome bars.


5 star rating: Highly Recommended May 2016

Sydney and her knowlege and delivery made this already interesting tour fun and entertaining. We had a great time and met some interesting people also on the tour. Make this tour was one of your first must do to launch your vacation in Chicago. We did and it feels that there is definitely more to Chicago than what meets the eye. Great tour indeed!

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