Walking Tour of Chicago’s Historical Bars


41 USD

Join us for a historical Chicago pub crawl with an educational twist! You’ll explore the city’s entertainment history and learn about prohibition, jazz, theatre, vices and social clubs, all while staying mostly indoors.

Duration: 2.5 hours
    Available in
  • English


  • Wander along Chicago’s Magnificent Mile
  • Check out the Tribune Tower and the Intercontinental Hotel
  • Drop by the Billy Goat Tavern and Michael Jordan’s Steak House


On this tour you’ll be shown historical photos and videos of Chicago on shared iPads, and visit 3 historical buildings for drinks.

We don’t walk far on this tour, giving us more time to engage with the city’s history. The short walking distance also gives us more time to enjoy our appetisers and drinks.

Many of our guests enjoy the social dynamic of this tour. It’s more than just a pub crawl – you’ll eat, drink, admire beautiful architecture and learn about Prohibition-era history and culture. Whether you’re a solo traveller, a couple or a group of friends, we’ll keep you entertained!

Please note that each participant must choose a beverage for the tour and bring cash to cover 2.5 servings: beer: $23 / wine: $29 / soda: $8 / water: $3.

The meeting point is inside Fannie May Candies, 343 N. Michigan Ave. Your guide will have a name tag and clipboard. The tour runs in a circle and ends one block north of the starting point. The total walking distance is 1.2 miles.

Link to a map of the meeting point:

What’s included & not included

  • Professional tour guide
  • Shared iPads with historical photos and video clips
  • Appetizers
  • Gift packets
  • Drinks and server gratuities

Check availability of the tour:

Meeting point

Fannie May Candies, 343 N. Michigan Ave.

Reviews from travellers (2)


Don't miss this one!
I had one evening in Chicago following a business meeting. Traveling alone, I wanted a quick way to see the city in the evening. The historic bar tour was AWESOME!! Our tour guide Elizabeth was phenomenal. I even ended up grabbing a drink with some Canadians in my group after. Totally made my trip!

Historic Bar Walking Tour
The tour was a lot of fun but the details are what made it for me. From the very beginning of the tour we were encouraged to really look at buildings to find details that told their stories. From all of the amazing info to the spot on coordination of food and drink I had a blast. Definitely check it out!

From 41 USD per person

Book a tour

Public tours
  • No booking fees
  • Pay by credit card or PayPal

Tour operated by: Chicago Detours

Select date and participants

We’re sorry to see you go.

Why didn’t you end up booking this tour?

Thanks for the feedback!

We’ll use it to improve the way you find and book tours on our site.