We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chicago Prohibition Tour

  • 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 a professional guide
Chicago Prohibition Tour
From USD 45.00
Check Availability
  • Overview
  • What to Expect
  • Important Information
  • Reviews
  • Q&A
Select Date and Travellers
Chicago Prohibition Tour
From USD 45.00
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.
What to Expect
Start your 3.5-hour Chicago Prohibition tour at Harry Caray's Italian Steakhouse — 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.
Reviews (125)
1 - 5 of 18 reviews
Reviewed 4 days ago
Fun and Informative Tour

Elizabeth was a wonderful tour guide! We really enjoyed all of the stops. The old buildings are really cool and there is good food and drink to be had. This isn't just a drinking tour. They tell you a lot about the history of Chicago...More

Date of experience: September 2018
Thank amies480
Reviewed 14 November 2018
History made fun

This tour was so much fun. Elizabeth was an excellent tour guide and gave us lots of information and history in a fun relaxed atmosphere. She was very helpful and friendly, told us what to try at each stop. The drinks were strong and delicious,...More

Date of experience: November 2018
3  Thank dianegTNgirl
Reviewed 5 October 2018
Tour with Family.

It was a great Tour. The drinks were good, but eat before you go, there isn't enough time to eat while touring.

Date of experience: July 2018
1  Thank Kathy B
Reviewed 3 October 2018
A great tour.

A really excellent tour with a great guide who was extremely friendly and highly organised. She had an amazing and detailed knowledge of the history of Chicago and especially of the prohibition era. We visited 5 prohibition era sites and enjoyed our time at each...especially...More

Date of experience: July 2018
3  Thank daveamiet
Reviewed 2 October 2018
Great tour

Elizabeth was out tour guide and gave an excellent tour with lots of interesting facts which was made even more interesting by her humours delivery the tour driver Kerry also chipped in with tips of local knowledge would recommend this tour

Date of experience: September 2018
Thank Tuggles52
View more reviews
Questions & Answers
Ask a question
10 January 2019|
AnswerShow all 2 answers
Response from dmb662 | Reviewed this property |
I believe the tour started at the Green Door Tavern. The tour does not end there so you will need to Ride Share or something both ways. It was summer when we went and walked about a mile or so to the first bar. The last... More
14 September 2018|
AnswerShow all 3 answers
Response from 242kristinac | Reviewed this property |
No children allowed.
24 July 2018|
Response from Shelley S | Reviewed this property |
There are four stops so at least $60 for drinks, more for food. I think we spent about $100.
Travellers Also Viewed
Gangsters and Ghosts Tour in Chicago
64 Reviews
from USD 27.00*
Chicago Crime and Mob Tour
539 Reviews
from USD 39.95*
Tommy Gun's Garage Dinner and Show
158 Reviews
from USD 67.00*
Historic Chicago Walking Bar Tour
57 Reviews
from USD 38.00*
Frequently bought together
Art Institute of Chicago Fast Pass...
53 Reviews
from USD 35.00*
Chicago Architecture River Cruise
3,324 Reviews
from USD 41.44*
Chicago Crime and Mob Tour
539 Reviews
from USD 39.95*
Special Offer
Skydeck Chicago Admission
627 Reviews
from USD 22.00*
USD 24.00