Historic Chicago Bars Walking Tour - 1 Day

Historic Chicago Bars Walking Tour

Get some history lessons on the Historic Chicago Bars Walking Tour with your pub crawl! Our walking tour of Chicago will show you the most authentic and historic Windy City bars!

Finally, a tour of a local Chicago tavern, pub, and dive bar. We’ll take you to five of Chicago’s most popular drinking establishments. These aren’t your typical tourist traps. These are the genuine article! The West Loop is the focus of the bar walking tour.

It’s a genuine Chicago neighborhood with local bars where folks can unwind and interact. At each pub, we’ll spend roughly 30 minutes. That should be ample time for you to meet some regulars and get a feel for the place. You can rely on us. You’ll want to return to one of these classic establishments the next time you visit Chicago or the neighborhood.

Walking tour to Chicago dive bars

It takes roughly 10 to 15 minutes to walk between pubs. You’ll have the opportunity to look about the area. Who knows, maybe you’ll want to relocate there someday. We’ll visit an Irish pub, some local taverns, and a dive bar. It’ll be a lot of fun. We’ll arrive at the intersection of Halsted, Grand, and Milwaukee, allowing you to quickly return to the loop or wherever you’re headed next.

You could even wish to continue the activities! It’s entirely up to you. This isn’t like any other pub tour you’ve ever been on. These are the Chicago drinking foundations that have been there for decades!

Highlights

  • Michigan Ave, aka “Magnificent Mile”
  • Tribune Tower
  • Chicago’s underground layers
  • The famous Billy Goat Tavern
  • A former historic jazz club and speakeasy
  • A 19th-century mansion

Historic Chicago Bars Walking Tour

Join us for an educational twist to a historic Chicago pub crawl! You’re going to explore the entertainment history of Chicago and learn about prohibition, jazz, theater, vices, and social clubs. In addition to the stories of the tour guide, guests interact on shared iPads with historic photos and videos to connect with the party past of Chicago.

Our evening walking tour remains predominantly indoors, making it great for any weather. At three drink stops, we will enjoy our appetizers and your choice of wine or beer and explore history and architecture between them. Our groups see magnificent lobbies, Gilded Age mansions, and multiple underground layers of Chicago as well as bar stops.

Haunted Chicago Ghost and Pub Walking Tour

Drinks are on you-see below, please.

Who’s coming on a Chicago historic pub crawl tour? Many visitors enjoy the fun and social dynamics of the tour. Travelers on their own often join us. It can be a fun thing to do with your boyfriend or girlfriend in Chicago as a great Chicago date idea. The tour is also made by groups of friends into a cool weekend event. It’s loved by family groups!

This tour is more than a historic crawl pub in Chicago–you’re going to eat, drink, and learn about architecture, history of the Prohibition Age, and party culture.

We’d like to say it’s a Speakeasy Tour or a Chicago Prohibition Tour, but in fact very few bars remaining in Chicago today have always been speakeasies. On our tour, however, we found one stop that was a real speakeasy and an early Chicago jazz club to boot!

The Historic Chicago Bar Walking Tour is like a mix of a food tour, a walking tour of architecture, and a movable documentary movie. Book your tour early as it often sells out the historic Chicago pub crawl. Doing this summer is a unique thing in Chicago!

Tour Highlights
• Michigan Ave, aka “Magnificent Mile”
• Tribune Tower
• Chicago’s underground layers
• The famous Billy Goat Tavern
• A former historic jazz club and speakeasy
• A 19th-century mansion

Stories and Ideas
• Architecture as a cultural artifact
• The “Hex of the Billy Goat”
• Chicago jazz era
• History of Chicago breweries
• Prohibition and gangsters
• 1960’s swanky nightlife
• Private clubs and debauchery

Historic Chicago Pub Crawl Prices
Reservations are $38.00 per person. Guests bring cash for beverages. Total cost is $39.00-$58.00 per tour guest inclusive of tour, food, beer, wine, gratuities, taxes.

Check availability

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