• Location: Chicago, Illinois
  • Duration: 2 hours 30 minutes (approx.)
From USD $ 38.00 View price calendar

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Explore downtown Chicago on a pub crawl with an educational twist! Your expert guide shares entertaining facts about the history of jazz, theater, social clubs, and the Prohibition era in the Windy City as you take in historic buildings and architecture. Use iPads to view historic photos and videos that accompany your guide’s stories as you stop in both famous and hidden bars for drinks and appetizers. A short walk allows plenty of time to see Chicago’s famous architecture and pubs on this tour – great for visitors and locals alike!


  • 2.5-hour walking tour of Chicago history, architecture and bars
  • Sip drinks and nibble on appetizers at three 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 Intercontinental Hotel on the Magnificent Mile
  • Admire the architecture that has made the Windy City famous

What You Can Expect

Historic Chicago Walking Bar Tour

The Billy Goat Tavern

Meet your guide to begin your pub, architecture and entertainment history tour. Start in the heart of Chicago’s legendary Magnificent Mile — or Mag Mile — a slice of Michigan Avenue packed with high-end shopping and landmark buildings, located between the Chicago River and Oak Street. Famous sites including the Wrigley Building, Tribune Tower, the Chicago Water Tower, and Allerton Hotel are found on Mag Mile.

Outside the neo-Gothic style Tribune Tower, note the bricks at the base of the building. In the early 1900s, the eccentric owner of the Chicago Tribune newspaper asked reporters to send rocks from famous buildings around the world; resulting in the display of more than 140 bricks that hail from the Taj Mahal, Westminster Abbey and World Trade Center, among other places.

Continue to the Intercontinental Hotel, where your guide explains its mixture of architectural styles. Marvel at large exterior carvings in Assyrian style; a Moorish-inspired gold dome; and learn about the mysterious motivations behind the exotic ornamentation of this skyscraper. 

Visit the original Billy Goat Tavern, a legendary bar that was immortalized in a Saturday Night Live sketch, and is also known as a favorite watering hole of local newspaper reporters.Your guide illustrates the tour with video and photographs on iPads provided for the tour and shared among your group. 

As you discover more historic architecture and stop into other bars, you'll learn more about jazz history, Chicago breweries, and the prohibition era's legendary mobsters such as Al Capone, part of Chicago's notorious crime syndicates. Have fun socializing and getting to know your group in a game learning about nightlife and entertainment in the neighborhood during the 1960s to win a prize! 

Expect to walk at a leisurely pace, covering a half mile in about 2.5 hours, with plenty of time to stop for drinks and appetizers at three historic bars. Appetizers are included. All guests must choose a beverage for the walking tour and bring cash to cover 2.5 servings of beer ($23), wine ($29), soda ($8) or water ($3).

Customer Reviews

Margaret K

5 star rating: Highly Recommended July 2018

This tour is a must do if you are visiting Chicago. Elizabeth our guide was very informative and had a great sense of humour. We started at the Tribune Tower which was very interesting. Highlights Billy Goat Tavern, the stories about Jazz and Prohibition. The food and drink were perfect.


5 star rating: Highly Recommended April 2018

I really enjoyed this tour. Our guide did a great job of keeping the whole group engaged and having fun while also learning a lot about Chicago history. I'm a bit of a history buff, but even I learned a lot that I did not know. It was a great experience to see some off-the-beaten-path places like the Billy Goat Tavern and the beautiful lobby area in the Intercontinental Hotel. I never would have gone to these places on my own.

Trudy H

5 star rating: Highly Recommended October 2017

Morgan was great. We learned a lot and had a fun group. Would highly recommend.

Melissa A

5 star rating: Highly Recommended March 2017

We had an awesome time on our walking tour of Chicago. The guide was friendly, professional, and knowledgable and the food/drink was perfect. I would recommend this tour 100.

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

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