Historic Chicago Walking Bar Tour

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  • Instant confirmation Confirmation is instant if you book 3 days before your tour
  • Mobile Voucher Accepted

What To Expect

On this historic Chicago pub crawl with an educational twist, explore Chicago's entertainment history and learn about prohibition, jazz, theater, vices, and social clubs.


  • Learn about the secrets of the Magnificent Mile, and the opulent 1920's lobbies

  • See Tribune Tower's Architectural Relic Collection, the 19th-century Gilded Age mansion and many more


Walking Tours in Chicago
Departs From:
Meeting Point:
Argo Tea inside Tribune Tower
2 hours and 30 minutes
Thursday, Friday and Saturday at 5:45 PM
Product Code:
Voucher info:
Paper voucher printout not required for this activity. You may show e-voucher from your mobile device.
Featured On:
Chicago City Tours & SightseeingChicago History and HeritageChicago Segway & Walking ToursCity Tours & SightseeingHistory and HeritageSegway & Walking Tours


Join us for a historic Chicago pub crawl with an educational twist! Explore Chicago's entertainment history and learn about prohibition, jazz, theater, vices, and social clubs, all while staying mostly indoors.

Interact with historic photos and videos on shared iPads and visit historic buildings for three drink stops. We don't walk far on our evening walking tour, giving us more time to engage with Chicago history and look at architecture. The limited walking distance on the tour gives us time to enjoy our appetizers and choice of wine or beer.

Tour groups see magnificent lobbies and really engage with some beautiful historic architecture. Many tour guests enjoy the social dynamic of this unique tour. Solo travelers often join the tour. Groups of friends make the tour into a cool weekend event as it’s more than a historic Chicago pub crawl - eat, drink, and learn about architecture, Prohibition-era history and culture.

It's a Speakeasy Tour or a Chicago Prohibition Tour, but truthfully very few bars in Chicago remaining today were ever speakeasies. We did find one stop on our tour that was a true speakeasy though! The Historic Chicago Bar Walking Tour is like a mix of a food tour, an architecture walking tour, and a mobile documentary film. Book your tour early as the historic Chicago pub crawl often sells out. It's a unique Chicago thing to do!


  • Engaging tour guide commentary

  • Shared use of iPads with video and photos

  • Appetizers at three stops

  • 2.5 servings of beer, wine, water or soda*

  • Special gifts


  • Meals and drinks

  • Personal expenses

  • Tips and gratuities

  • Optional activity costs

Please Note

*You will have to pay cash at start of tour to cover all server gratuities and chosen beverage option (2.5 servings total): 20 USD for beer, 22 USD for wine, 6 USD for soda, 3 USD for water.

  • Tour takes approximately 2 hours and 30 minutes. Walking distance is approximately .75 mile (approx. 1.2 kilometers)

  • Please wear comfortable clothing and shoes.

  • Our tours will run even during rainy days.

  • Tours run year-round and during rain because we stay mostly indoors.

Cancellation Policy

  • 100% cancellation fee. Non-refundable.

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