Historic Chicago Walking Bar Tour for UChicago Alumni

Historic Chicago Pub Crawl Tour Overview

Join fellow University of Chicago alumni on a historic Chicago pub crawl with an educational twist! On this mostly indoor walking tour, you’ll explore Chicago’s entertainment history and learn about prohibition, jazz, theater, vices and social clubs. We'll enjoy our appetizers and choice of wine or beer at three drink stops and some history and architecture in between.

Special for this tour, we are offering 20% off the regular tour price.

You'll see a secret side to Michigan Avenue and explore Chicago’s entertainment history and learn about prohibition, jazz, theater, vices and social clubs. In addition to the tour guide's stories, guests interact with historic photos and videos on shared iPads to connect with Chicago's party past.

Our afternoon or evening walking tour stays mostly indoors, making it great for any kind of weather. We'll enjoy our appetizers and choice of wine or beer at three drink stops and explore history and architecture in between. In addition to bar stops, our groups see magnificent lobbies, Gilded Age mansions, and Chicago's underground layers. You'll also hear about the infamous Curse of the Billy Goat over a bite of a "cheezborger."

In addition to bar stops, our groups see magnificent lobbies, Gilded Age mansions and Chicago's multiple underground layers. And you get to hear about the Curse of the Billy Goat being broken when the Cubs won the World Series! We even look at a building that was an early Chicago jazz club.

In addition to the tour guide's stories, guests interact with historic photos and videos on shared iPads. This tour is more than a historic Chicago pub crawl. You’ll eat, drink and learn about architecture, Prohibition-era history and party culture.

Who wants to listen to a volunteer tour docent rambling a bunch of memorized dates and names? Not us! Our expert tour guides are highly trained, smart, fun and passionate about Chicago architecture and history.

In business since 2010 and founded by a UChicago Alumna, we are proud to be a top-rated Chicago tour company with five-stars on Yelp and TripAdvisor. Many of our Chicago architecture walking tours integrate historic bars, food and music history. We hope you'll join us to explore stories and places locals don't even know, both downtown and in Chicago neighborhoods!

The Historic Chicago Walking Bar 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 at any time of the year!

Got a time conflict? Send us an email at info@chicagodetours.com as other times may become available. Or please join us on the public version of this walking tour that is run year round.

This Chicago architecture walking tour is also available as a private group tour for nine or more guests and really popular as a fun corporate team building event in Chicago.

Chicago Detours Executive Director, Amanda Scotese and Content Manager, Alex Bean - both UChicago Alumni - will lead a walking tour. Book your tour now as space is very limited and our events with the University of Chicago Alumni Association almost always sell out. Feel free to add yourself to a waitlist if your preferred tour time is sold out as spots may open up.

If you're curious about our Executive Director and UChicago alumna Amanda Scotese, read more here about her background or connect on LinkedIn.

Walking Bar 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 “Curse of the Billy Goat”
• Jazz Age Chicago
• History of Chicago breweries
• Prohibition and gangsters
• 1960s swanky nightlife

Chicago Walking Bar Tour Includes:

• Engaging tour guide commentary
• Shared use of iPads with historic photos and video clips
• Appetizers
• Special gifts
• Discounted flat-rate $15 parking at the Grant Park North Garage (ask for voucher at tour  check-in)

Tour Reservations Do 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).

Walking distance: .75 miles