4.5 star rating: Recommended 11 Reviews

5 star
4 star
3 star
2 star
1 star
  • Location:Chicago, Illinois
  • Duration:2 hours 30 minutes (approx.)

Historic Chicago Walking Bar Tour

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 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

Meet your guide inside the Tribune Tower 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; please choose to drink wine or beer, soda, or water during the tour and bring cash to cover your drinks.

Customer Reviews

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

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.

5 star rating: Highly Recommended May 2015

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

5 star rating: Highly Recommended March 2015

The guide was fantastic and well educated. Enjoyed the tour from A to Z.

5 star rating: Highly Recommended March 2015

We loved our tour guide, Elizabeth! She was great and made our tour really fun and interesting. Thank you!

5 star rating: Highly Recommended August 2014

I went by myself on this bar crawl tour of Chicago and it was a blast! I was afraid I would be uncomfortable without anyone to go with me, but I ended up leaving with new friends. The guide, Elizabeth, was incredibly knowledgeable about the city and very approachable. It's clear that she loves Chicago and she was excited to share it with us. Instead of the talking head I am used to on most tours, she was engaging and got the group participating in the discussion. There was even a fun trivia game!

The tour was the perfect combination of Chicago history, hidden and well-known Chicago architecture, and beer (or wine/soda - they had multiple options, but I had beer). I got to hop around to places I never expected to see like Phil Stefani's 437, which I never would have known existed and much less that it has some cool jazz and gangster history, all the while enjoying a beer at each stop. The postcard memento of 437 everyone gets was a nice touch too. The Billy Goat Tavern was my favorite stop as I had heard of it and seen the SNL sketch, but never knew where it was or its history. After hearing the story behind the goat from Elizabeth, I can't wait to take friends to the spot.

Being fairly new to the city, I feel more like a local after this excursion. I saw hidden bits of Chicago that I never would have noticed and that I don't think most Chicagoans even know about. I will definitely bring friends and family on this tour when they come to town.

4 star rating: Recommended August 2015

I'm a Chicagoland native currently living in the city. This tour was fun, not too touristy, and I learned things about the city I'm living in. Elizabeth was knowledgeable, approachable, and fun. I would recommend this to both visitors and natives.

4 star rating: Recommended August 2015

I really enjoyed the tour. The guide was very good and helpful. You pay for your drinks at the start which saved time and hassle. The cost of the drinks was very good and it included the tips. Worth doing

4 star rating: Recommended July 2015

Tour was excellent. The beginning was a bit confusing. We met in a tea room and it seemed a bit disorganized. We would have liked to have beer or wine at one or two of the stops and the option of soda or water for the final stop.

4 star rating: Recommended June 2015

We did the historic walking bar tour and it was great. It was a lot more informative and educational than I expected and we only stopped in to 2 bars but it was great. The group we were with was great fun and we all actually went out together after the tour. Our tour guide was very knowledgeable and a lot of fun. I would recommend this tour for a fun informative evening.

From USD $ 33.99

View price calendar

Low Price Guarantee

Select Travel Date

Flexible Date Guarantee

Enter Total Number of Travelers

What's this, and can I change it?

Please note: After your purchase is confirmed we will email you a link to your voucher.
What's this?

Tour code: 6475CHIBAR


Viator uses cookies to improve your experience on our website. Learn more about how we use cookies and how to change your cookie settings | Close message