Historic Chicago Walking Bar Tour Pub Crawl

A private group tour event with drinks, architecture and an educational twist.

Drink, eat and learn on this historic Chicago pub crawl tour with an educational twist. You’ll learn about Chicago entertainment history as you experience fascinating architecture. Venture off the tourist thoroughfare of the Mag Mile to visit overlooked spots of Chicago entertainment history for your private group walking tour of bars in historic buildings.


Your professional Chicago tour guide will tell forgotten stories of prohibition, theater, jazz, vices and nightlife. You’ll step inside opulent 1920s architecture and learn the secret background of fraternal men’s clubs. This is more than another Chicago prohibition tour! Great for Chicago locals or first-time visitors, this walking tour will give your private group a whole new perspective on looking at architecture, as well as Chicago’s good-time culture.

Available year-round, this top-rated tour stays primarily indoors during all weather.

On this top-rated Chicago tour, your private group tour guests will share iPads with archival maps, historic Chicago photos and documentary video clips while the tour guide shares stories of Chicago history.

As a private walking tour of Chicago, this unique experience makes for a memorable birthday party or a fun corporate team-building event. If you’re looking for an evening tour, it works well after a long day of meetings in downtown Chicago.


Private groups have the option to upgrade the tour to include a full meal as a premium “dine-around” food tour. You’ll get an appetizer at the first stop, an entree at Lawry’s the Prime Rib, and artisanal chocolate cake in the historic Intercontinental Hotel. Please call us at 312.350.1131 for more details on the dine-around food tour option and to book your private group tour.


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!

As you look into possibilities for your Chicago private tour, this quick guide may help you determine if Chicago Detours will be the best Chicago tour company for your special event.

This Chicago architecture walking tour is also available regularly as a public tour for eight or less guests and is a great Chicago date idea.


2.5 Hours


.75 Miles


  • Secrets off the Mag Mile
  • Tribune Tower architecture
  • The famous Billy Goat Tavern
  • Chicago’s underground layers
  • An early jazz club and speakeasy
  • 19th-century Gilded Age mansions
  • Opulent 1920s lobbies
  • Architecture in its historic context
  • The Cubs’ “Curse of the Billy Goat”
  • Chicago jazz history
  • Prohibition and gangsters
  • Dining of the past
  • Vices and nightlife of the ’60s
  • Social clubs and parties

Tour Includes

  • Engaging tour guide commentary
  • Shared use of iPads with video and photos
  • Appetizers at three stops
  • 2.5 servings of beer, wine or soda
  • All taxes and server gratuities
  • Please inquire for Dine-Around Tour details.

Get More Info

Get More Info

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