Historic Chicago Walking Bar Tour


Sightseeing  :  United States  :  Illinois  :  Chicago  :  Walking Tours
  • Historic Chicago Walking Bar Tour

Chicago, Illinois

Rating:  4.5 stars4.5 stars4.5 stars4.5 stars4.5 stars
Trip Type:   Walking Tours
Duration:  2 hours 30 minutes
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!

More About This Activity All Walking Tours  →

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!Meet your guide inside the Tribune Tower 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; please choose to drink wine or beer, soda, or water during the tour and bring cash to cover your drinks.




« Go Back


About Us | Link With Us | Contact Us | List With Us | Privacy Policy | Legal
Also visit Tours.com, the official directory of vacations worldwide since 1995.

Copyright 2025 Tours.com/Select Web Ventures, LLC - All Rights Reserved.
No part of this website may be copied or reproduced without the written consent of Tours.com and Select Web Ventures, LLC.