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Walk through downtown Chicago on a 2.5-hour tour to three historic bars, and learn from a local guide about the history of jazz, theater, social clubs and the Prohibition era in the Windy City. Stroll down Michigan Avenue past landmark buildings such as the Tribune Tower and InterContinental Hotel Chicago, stopping at popular drinking establishments for complimentary appetizers and the opportunity to purchase drinks. You’re entertained along the way with anecdotes accompanied by photos and videos via iPads. This evening tour is perfect for locals and visitors alike!


  • 2.5-hour walking tour of Chicago history, architecture and bars
  • Sip drinks and nibble on appetizers at three historic pubs as you learn about the city’s history
  • See secret spots from the entertainment world of 20th-century Chicago, including a former speakeasy and jazz club from prohibition times
  • Take in landmark buildings including the Tribune Tower and Intercontinental Hotel on the Magnificent Mile
  • Admire the architecture that has made the Windy City famous

Recent Photos of This Tour

What You Can Expect

Historic Chicago Walking Bar Tour

Magnificent Mile

Start your bar-hopping tour of historic Chicago at the Tribune Tower, located across from the Wrigley Building in the heart of Chicago’s legendary Magnificent Mile. Learn from your guide about the building’s brick foundation, made from stones sent from worldwide landmarks including Westminster Abbey, the World Trade Center and the Taj Mahal.
Follow on foot at a leisurely pace to three Prohibition-era speakeasies and other historic watering holes like the Billy Goat Tavern — a favorite establishment of newspaper reporters that was popularized in a Saturday Night Live sketch. Enjoy complimentary appetizers and perhaps order a beer, a glass of wine, soda or other drink (see Important Info tab on pre-purchased beverages).
This 2.5-hour evening walking tour takes you past many renowned edifices on Michigan Avenue, such as the Chicago Water Tower and art deco–style Warwick Allerton Hotel Chicago. Stroll past the InterContinental Hotel and marvel at its blend of ornamental designs, from Assyrian-style exterior carvings to the Moorish-inspired gold dome.
Along the way, take a look at photos and videos on iPads provided by your entertaining guide, and learn about Chicago’s jazz and beer history and notorious gangsters like crime boss Al Capone. You can even compete for a prize in a game about city nightlife during the 1960s.

Expect to walk about half a mile (.8 km) before wrapping up your tour near the starting point.
All guests must choose a beverage for the walking tour and bring cash to cover 2.5 servings of beer ($20), wine ($22), soda ($6) or water ($3).

Customer Reviews

Kevin M

5 star rating: Highly Recommended December 2016

Pawel was an awesome tour guide! He was fun and made history fun. He was full of fun facts and historical details and while I typically am not at all interested in history, I found myself very interested. The wine and beer at the Billy Goat Tavern was blech!, but cheeseburger was great. The other bar stops The Marriott's Rush and the Intercontinental were all very tasty, including the beer and wine. We look forward to taking another Chicago DeTour again when we are back in town.

Thomas S

5 star rating: Highly Recommended November 2016

Excellent introduction to the city for first time visitors.

Linda B

5 star rating: Highly Recommended October 2016

We very much enjoyed this tour with Pavlo. It is called a Historic Walking Bar Tour, but probably should be called an Architectural Walking bar tour as you get an overview of some key buildings along the way, in additional to visiting some fantastic locations to enjoy your beverages with nibbles. If you just want to get merry and learn about the drinking scene, then this is not the tour for you, but if you want your eyes opened to to some amazing locations and buildings whilst enjoying some good company, good nibbles, with an excellent passionate guide, then do book this tour as we very much enjoyed al the history, architecture, stories and drinks. By the end of the tour, we felt we knew everyone in our small group of 8. Recommended!

terri m

5 star rating: Highly Recommended September 2016

The tour was tons of fun. Elizabeth made it so! It was interesting. I enjoyed the small group and met some wonderful people. we even enjoyed dinner afterwards at Grand Lux Cafe. I highly recommend this tour.

Camilo R

5 star rating: Highly Recommended March 2016

Guide with great attitude, very well selected places to visit, learn and enjoy

Marco H

5 star rating: Highly Recommended March 2016

interesting and cultural tour

margaret m

5 star rating: Highly Recommended December 2015

Had a wonderful time ! Elizabeth does a super job including everyone and making this a great tiem.

Michael B

5 star rating: Highly Recommended October 2015

The tour was great! I would highly recommend it. Our tour guide was incredible, even taking the time to remember all of our names. My wife and I learned a lot and had a great time.
Michael 'Smoothy' Washington

Linda G

5 star rating: Highly Recommended September 2015

Unfortunately I can't rate this one as I missed it due to my lack of navigation skills - I got lost on the way! I'm sure it was great and I was really dissappointed to have missed it.

Jana R

5 star rating: Highly Recommended May 2015

I highly recommend this tour....our guide was so passionate. So much fun.

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