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!

Highlights

  • 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.

Customer Reviews

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.

Mary A

5 star rating: Highly Recommended March 2015

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

Lauren H

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!

Jennifer K

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.

Jennifer D

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.

From USD $ 36.00

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Tour code: 6475CHIBAR

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