1. United States
  2. Illinois
  3. Chicago
  4. The Magnificent Mile

Chicago Bars: Historic Walking Tour

Product ID: 20518
Uncover the scandalous history of Chicago's Prohibition Era clubs and speakeasies, and learn all about the city's historic culture of entertainment, grand balls, and soirees. Enjoy a fun 2.5-hour walking tour with drinks, appetizers, and great company!
About this activity
Duration: 2.5 hours
Check availability to see starting times.
Printed or mobile voucher accepted
Instant confirmation
Live tour guide
Free cancellation up to 24 hours before activity starts

Select participants and date:



  • Explore 3 bars significant to the story of Chicago's fun past
  • Learn the fascinating, and often sordid, history of Chicago's jazz clubs and speakeasies
  • Share iPads with illustrations, photos, maps, and video clips from Chicago's past
Full description
Learn the hidden history of Chicago's Mag Mile, visiting the sites of the Jazz Age's speakeasies and grand balls while enjoying drinks and good company at great bars.

Share iPads with your group to see photos and video clips from bygone eras while your guide regales engaging stories and scandals from a fascinating segment of American history.
Enjoy light appetizers and choice of wine or beer at three drink stops and explore history and architecture in between each stop.  See magnificent lobbies, Gilded Age mansions and Chicago’s multiple underground layers. Hear about the Curse of the Billy Goat, which was broken when the Cubs won the World Series!

The tour takes place primarily indoors, making it an ideal activity during both the shivering winters and the sweltering summers. Enjoy drinks and light appetizers along the way as you uncover Chicago's past.
  • Shared use of iPads with historic photos and videos
  • Valuable gift packet
  • Light appetizers
What’s Not Included
  • Drinks
  • Gratuities

Prepare for the activity

Meeting point

Inside Fannie May Candies, 343 N. Michigan Ave

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Important information
Know before you go
• Guests are required to come to the tour with cash for drinks, beer or wine only, as well as gratuities for the servers
• Guests drinking beer or wine will be given 2 regular servings plus 1 sample size
• Even if a guest does not drink alcohol they must order a beverage, even just a water
• Special tour drink rates includes 2.5 drinks and server gratuities: Wine – $29, Beer – $23, Water – $3
Customer reviews

Overall rating

4.8 / 5

based on 24 reviews

Review summary

  • Service
    4.8 / 5
  • Organization
    4.8 / 5
  • Value for money
    4.4 / 5
  • Safety
    5 / 5
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Great Tour Guide...and fun tour!

The tour was fun and educational. I loved the Tribune Tower! The pubs were great! I do wish I had understood that the drinks were extra. I would think a "pub crawl" would include drinks, so, instead of costing my husband and I $80.00, it was $132.00 total for the two of us....worth it, but, I would just like to pay it all up front. Anyway....I would do it again!

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February 24, 2018

Cool tour for a fun date downtown!

Loved this tour! My boyfriend and I were having a "tourist" day downtown and took the Inside the Loop tour by Chicago Detours as well. It was so much fun! This tour of historic bars made for a great date. Though we're both locals, we had so much to learn. And the guide, who was the same from our earlier tour, was wonderful. She really knows how to tell a story, instead of just spouting out facts. And the visual aids are such a great addition to the stories. I would highly recommend this tour.

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August 13, 2013

Educational and fun

A very intimate setting combined with fun stories, architecture history, good bees and good snacks made this a worthwhile excursion. The guide was very knowledgeable, fun and entertaining.

June 23, 2019

Organized by

Chicago Detours

Product ID: 20518