Historic Chicago Walking Tour in Chicago, IL

Fannie May CandiesChicago, IL 60601
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TripAdvisor user rating 5.00 out of 5 Based on 759 reviews

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Presented by Chicago Detours, Historic Chicago Walking Bar Tour offers a 2.5-hour experience sampling some of the area’s best eats and drinks, seeing the beautiful architecture and learning about its history from the Prohibition era. Highlights include Tribune Tower, the famous Billy Goat Tavern, a 19th-century mansion, a former historic jazz club and speakeasy, Magnificent Mile and more.

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from Historic Chicago Walking Bar Tour
Join us for a 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, all while staying mostly indoors.

On this tour, guests 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. Also 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 as it’s more than a historic Chicago pub crawl – you’ll eat, drink, and learn about architecture, Prohibition-era history, and culture.

We’d like to say 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!

Chicago Bar Tour Highlights:
  • Michigan Ave/Magnificent Mile
  • Tribune Tower
  • Intercontinental Hotel
  • Chicago Underground
  • Billy Goat Tavern
  • Phil Stefani’s 437 Rush (early jazz club and speakeasy)
  • A 19th-Century Mansion
  • Michael Jordan’s Steakhouse

Stories and Ideas on the Historic Chicago Pub Crawl Tour:
  • Architecture as a cultural artifact
  • The “Hex of the Billy Goat”
  • Chicago jazz era
  • History of Chicago breweries
  • Prohibition and gangsters
  • Historic restaurant trends
  • 1960’s nightlife
  • Private clubs

Walking Bar Tour Includes:
  • Engaging tour guide commentary
  • Shared use of iPads with historic photos and video clips
  • Gift packets
  • Appetizers

Walking Tour Does Not Include:
  • Drinks and server gratuities. All guests must choose a beverage for the walking tour and bring cash to cover 2.5 servings of beer ($23), wine ($29), or water ($3).

We meet at Fannie May Candies, 343 N. Michigan Ave. Look for the guide with the name tag and clipboard. We make a circle so that the tour ends one block north of our starting point.

Link to meeting point map:

Historic Chicago Walking Bar Tour Reviews

Terry Rauscher Tripster User Profile Image
Terry Rauscher
1 Review
"Walking bar tour"
October 2016
I recently had the pleasure of visiting Chicago. A friend and myself decided to try the walking pub tour. The tour itself was very interesting and the guide was very knowledgeable. The down side of this was the food and drink. The cost for 2 and 1/2 beers was $18 and barely enough time to guzzle them down. The appetizers that were a joke at Billy Goat tavern twelve of us shared 3 hamburgers yes 1/4 for each ! It got worse when we stopped at the Marriott and our snack there was 1/2 deviled egg each ! I did not expect a lot but that was ridiculous.
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Tip: eat first, drink later some where other than the tour.

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Frequently Asked Questions about Historic Chicago Walking Bar Tour

How early should I arrive?
We suggest arriving 10-15 minutes prior to your tour time. Also, consider time for parking.

Where does the tour begin?
You will meet inside Argo Tea at 435 N. Michigan Ave, which is Tribune Tower.

Where does the tour end?
The tour makes a circle so that it ends one block north of our starting point. 

Are drinks included?
No, we don’t include the drinks in the Historic Chicago Bar Tour. We want to give non-drinkers the option of soda and water, and give drinkers the option of wine and beer. These are all at different price points and paid for in cash at the start of the tour. Just fyi, while this could be called a pub crawl, it’s definitely an educational pub crawl.

What should I wear?
We suggest comfortable walking shoes. Please be prepared to walk or stand for the tour duration. We advise a bathroom break. While we are not outside for most of the duration of our Chicago walking tours, please come prepared, i.e. water, umbrella.

Is parking available?
Chicago Detours offers our guests a special discounted rate for parking at the Grant Park North Garage, accessible from Michigan Avenue at Randolph Street. Rate is $15 ($38 value), valid up to 12 hours. Upon check-in for the tour, ask the tour guide for a voucher for the discounted rate. This is four blocks from the tour meeting point, and right at the tour end location.

Is audio, video or photography allowed?
Please no video or audio recording devices. Minimal note-taking permitted. Photography during tour is welcome – but don’t get left behind!

Does the walking tour operate rain or shine?
Rain or shine we go! No refunds. In the case of serious conditions, we’ll call you.

Is the tour appropriate for children?
The Historic Chicago Bar Walking Tour enters into bars and is most appropriate for teens age 16 and up.

Are there bathrooms on the tour?
We advise a bathroom break before the tour.