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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 (52)
1 - 5 of 25 reviews
Reviewed 2 weeks ago 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 weeks ago

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!

Reviewed 29 August 2018
terrific way to spend a couple of hours in the city

Our first ChicagoDetours venture -- very enjoyable. Our tour leader was a JOYFUL history-nut and made the stops at the ChiTrib and bars a lot of fun.

Thank Daniel C
AmandaDetoursOwner, Manager at Chicago Detours, responded to this reviewResponded 7 September 2018

Thanks for this review, Daniel, and for joining us for the Historic Chicago Walking Bar Tour! We're so glad your first tour with us was a good experience and hope you'll join us for another soon!

Reviewed 17 August 2018
Great way to spend your birthday!

Took this tour with a group of friends and family for a birthday . Nice off the beaten path walking tour and some great insight into the history of some of the bulldings the bars are in .. Many of these places you walk by...More

Thank Napervillefoodtour
AmandaDetoursOwner, Manager at Chicago Detours, responded to this reviewResponded 25 August 2018

Thanks for joining us for a tour and sharing this review! We love taking people to places and sharing stories even locals don't know. It sounds like you had a great time, and it was our pleasure to be a part of your special celebration....More

Reviewed 17 August 2018
Don't waste your time

I had high expectations for this tour but was severely disappointed. It started out ok - saw the rocks/bricks in the Chicago Tribune building except it felt like Elizabeth, the tour guide, was a little patronizing with her questions to make us think, like we...More

Thank mujerlinda
AmandaDetoursOwner, Owner at Chicago Detours, responded to this reviewResponded 25 August 2018

We are disappointed to hear our tour did not meet your expectations. Elizabeth has so many five-star reviews on TripAdvisor that your critique is really a surprise to us. That said, we understand that our tours are not for everyone! Regarding the tips, they are...More

Reviewed 2 August 2018 via mobile
So much fun

This was a great time! We had good beer, learned things and explored new places. I would do another tour next visit.

Thank H P
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