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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. 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. Drinks are on you - please see below. 

Tour groups see magnificent lobbies and really engage with some beautiful historic architecture. This is not a typical "pub crawl." We go into a variety of bars as we discuss history. One bar is historic, another is in a very historic building, and the third is newer and on a historic site. 

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.

Who wants a tour with a volunteer tour docent rambling dates and names? Don’t fret with us – our tour guides are highly trained, smart and fun! We are proud to be a top-rated Chicago tour company, with five-star ratings on Yelp and TripAdvisor.

Discounted $15 flat-rate parking is available for Chicago Detours guests at the Grant Park North Garage (ask for voucher at tour).

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 that we view from the outside! 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. 

Chicago Bar Tour Highlights
  • Michigan Ave/Magnificent Mile
  • Tribune Tower
  • Intercontinental Hotel
  • Chicago Underground
  • Billy Goat Tavern
  • A building that was an early jazz club and speakeasy
  • A 19th-Century Mansion


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


Historic Chicago Pub Crawl Bar Tour Includes
  • Engaging tour guide commentary
  • Shared use of iPads with historic photos and video clips
  • Gift packets
  • Appetizers

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USD 41.00
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