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Historic Chicago Walking Bar Tour

From US$38.00
  • 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
Historic Chicago Walking Bar Tour
From US$38.00
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  • Overview
  • What to Expect
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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!
What to Expect

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).
Reviews (56)
1 - 5 of 29 reviews
Reviewed 2 weeks ago
Interesting and Educational

Great to get to know the city through historic details and stories. Our guide was excellent and pointed out several architectural details that we would have missed otherwise.

Date of experience: November 2018
Thank Katie P
AmandaDetoursOwner, Manager at Chicago Detours, responded to this reviewResponded 1 week ago

Hi Katie, thanks for sharing a review of the Historic Chicago Walking Bar Tour! We're glad you enjoyed all the architectural details so many people walk past every day without noticing! Thanks for coming on the tour with us.

Reviewed 6 November 2018
Best way to tour the city

Awesome way to tour the city, learn the history and have a few drinks! My tour guide was super knowledgeable and very passionate about Chicago. I would 100% recommend to anyone vising the city who has a love for history! Only improvements could be a...More

Date of experience: November 2018
Thank Excursion51784047916
AmandaDetoursOwner, Manager at Chicago Detours, responded to this reviewResponded 3 weeks ago

We're glad you had a good time on our Historic Chicago Walking Bar Tour. Thanks for your review and your feedback!

Reviewed 18 October 2018
Education can be fun!

My husband and I took the tour while in Chicago for a conference. We both thoroughly enjoyed the experience! Our guide was great-very organized and knowledgeable. We liked the mix of history, architecture, and bar stops. The tour started on time and was easy to...More

Date of experience: October 2018
Thank Jody E
AmandaDetoursOwner, Manager at Chicago Detours, responded to this reviewResponded 1 November 2018

Thanks for joining us Jody and for sharing this review! We're so happy you were able to get out and explore the city with us a little bit during the conference.

Reviewed 17 October 2018 via mobile
Came with high hopes, wasn’t disappointed

Great walking tour of Chicago. Glad we had the iPads to provide a little extra information and visuals. Enjoyed every stop, great history and some good little eats too. A must do to get your feet wet in Chicago.

Thank g_whitloc
Reviewed 25 September 2018 via mobile
Fun little tour

This is a fun little walking tour that includes a little bit of everything about Chicago history and architecture. You pay the cost of the tour then it’s $23 extra (beer option) once you arrive for the tour for 2.5 glasses during the tour. Morgan...More

Thank ans6c
AmandaDetoursOwner, Manager at Chicago Detours, responded to this reviewResponded 2 October 2018

Thanks so much for coming on our tour and posting a review! The interactive dynamic of the Historic Chicago Walking Bar Tour is a great way to meet people and have some fun in Chicago. We're so glad you had a good time with us!

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Judy M
4 November 2018|
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