Historic Chicago Walking Tour in Chicago, IL

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:
https://www.google.com.my/maps/place/Fannie+May/@41.8880344,-87.626475,17z/data=!4m5!3m4!1s0x880e2caedb378317:0x27ecb374ec7d52e8!8m2!3d41.8880344!4d-87.6242863?hl=en