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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).
Write a ReviewReviews (48)

1 - 5 of 22 reviews

Reviewed 2 days ago
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
Reviewed 2 weeks ago 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
Reviewed 2 weeks ago
Notice the details

Great way to see the city. Interesting to get the history and explanation of buildings you might have just hurried past. Our guide, Emily, was fantastic.

Thank Joanne K
Reviewed 3 weeks ago
Must Have element for short trip to Chicago

A fantastic tour. We didn't cover much distance but covered a HUGE amount of Chicago history and culture. From jazz to prohibition,gangsters,baseball,and the rapid growth of the city. Underground( loved The Goat bar!), overground and between some iconic buildings and into some dark,hidden corners. Our...More

Thank MARK N
Reviewed 4 weeks ago
Fun and informative

My wife and I took my brother on the Historic Chicago Walking Bar Tour for his 30th birthday. The Chicago Detours website made it sound interesting, and it was well-reviewed here, so our expectations were high. All of them were exceeded. The amount of fascinating,...More

1  Thank Dave B
AmandaDetoursOwner, Manager at Chicago Detours, responded to this reviewResponded 4 weeks ago

Thanks, Dave! We're so pleased to have been included in your special birthday celebration for your brother. It's so much fun for us to share Chicago history with our guests, and even more fun when it's for a special occasion! Thanks again.

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