Historic Chicago Walking Bar Tour

Eat, drink and learn about architecture and party times of Chicago history!

See a secret side to Michigan Avenue on this historic Chicago pub crawl with an educational twist! You’ll explore Chicago’s entertainment history and learn about prohibition, jazz, theater, vices, and social clubs. In addition to the tour guide’s stories, guests interact with historic photos and videos on shared iPads to connect with Chicago’s party past.


Our afternoon or evening walking tour stays mostly indoors, making it great for any kind of weather. We’ll enjoy our appetizers and choice of wine or beer at three drink stops and explore history and architecture in between. In addition to bar stops, our groups see magnificent lobbies, Gilded Age mansions, and Chicago’s underground layers. You’ll also hear about the infamous Curse of the Billy Goat over a bite of a “cheezborger.”

Who comes on a historic pub crawl tour of Chicago? Many tour guests enjoy the tour’s fun and social dynamic. Solo travelers often join us. As a great Chicago date idea, it can be a fun thing to do in Chicago with your boyfriend or girlfriend. Groups of friends make the tour into a cool weekend event, too. Family groups love it!

This tour is more than a historic Chicago pub crawl – you’ll eat, drink, and learn about Chicago architecture, Prohibition-era history, and party culture on this educational walking tour.

This tour goes beyond a typical pub crawl, if by chance you’ve gone on one in other cities. Our tour is fun and educational, and we run it streamlined like a special event. Drinks are usually ready when we get to each spot versus having to wait in line. You will really engage with beautiful historic architecture. We discuss history as we go into a variety of bars from different eras. One is a historic bar, another is a newer bar on a historic site, and for the third we get drinks in the atmospheric lobby of a historic hotel.

We’d like to say it’s a Speakeasy Tour or a Chicago Prohibition Tour, but in truth, very few bars are left in Chicago that were ever speakeasies. One site on our tour that we see from the outside was a true speakeasy and early Chicago jazz club though!


Who wants to listen to a volunteer tour docent rambling a bunch of memorized dates and names? Not us! Our expert tour guides are highly trained, smart, fun and passionate about Chicago architecture and history.

In business since 2010, we are proud to be a top-rated Chicago tour company with five-stars on Yelp and TripAdvisor. Many of our Chicago architecture walking tours integrate historic bars, food, and music history. We hope you’ll join us to explore stories and places locals don’t even know, both downtown and in Chicago neighborhoods!

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 at any time of the year!

Got a time conflict? Consider our 1893 World’s Fair Tour with Bars.

This Chicago architecture walking tour is also available as a private group tour for nine or more guests and really popular as a fun corporate team building event in Chicago.


2.5 Hours


.75 Miles


  • Days & Times
  • Monday
  • Tuesday
  • Wednesday
  • Thursday
  • Friday
  • Saturday
    2:00pm & 5:45pm
  • Sunday


  • Michigan Ave, aka "Magnificent Mile"
  • Tribune Tower
  • Chicago's underground layers
  • The famous Billy Goat Tavern
  • A former historic jazz club and speakeasy
  • A 19th-century mansion

Stories & Ideas

  • Architecture as a cultural artifact
  • The “Curse of the Billy Goat”
  • Jazz Age Chicago
  • History of Chicago breweries
  • Prohibition and gangsters
  • 1960’s swanky nightlife

Tour Includes

  • Engaging tour guide commentary
  • Shared use of iPads with historic photos and video clips
  • Appetizers
  • Special gifts
  • Discounted flat-rate $15 parking at the Grant Park North Garage (ask for voucher at tour  check-in)

Tour Reservations Do Not Include:

Drinks and server gratuities. All guests must choose a beverage for the walking tour and bring cash to cover the gratuities and 2.5 servings of beer ($23), wine ($29), or water ($3).

Tour Reviews

The amount of fascinating, surprising, offbeat information packed into this two and a half hour walking tour was amazing. Our tour guide was funny and knew his stuff. The bar tour itself takes you to some amazing hidden-in-plain-sight spots downtown, and includes a couple of beers and some good snacks as well. Highly recommended!
Dave B.

Tour Meeting Spot

  • Tour meets INSIDE Fannie May Candies, 343 N. Michigan Ave.
  • Remember to bring cash for drinks (see above)!
  • Tour ends inside the InterContinental Hotel, 505 N. Michigan Ave.

Book Now

Call Us: 312.350.1131
E-Mail Us: [email protected]