Skip to main content
Book a private virtual tour for conferences and corporate events

Chicago Architecture Crash Course Walking Tour

A creative tour of Chicago architecture designed for curious people.

What does Michael Jackson’s Thriller have to do with the design of a Postmodern skyscraper? Or Andy Warhol’s soup cans with Miesian Modernism? The Chicago Architecture Crash Course Walking Tour is a creative tour of Chicago architecture that answers those questions. We designed it for curious people who love finding connections.

Please see our walking tour FAQ for details on our safety precautions and policies during the COVID-19 Pandemic.

PLEASE NOTE: This tour is temporarily suspended but can be booked as Private Tour. Call us at 312.350.1131 for details on booking a Private Tour. Check back to soon or join our mailing list to find out when we’re offering this tour again to the public!


On this condensed Chicago architecture walking tour of an hour and a half, you will learn about architectural styles through their connections with technology and culture. All arts are a reflection of their age. This walking tour compares architecture with contemporaneous works in other media to help us learn how to identify architectural styles.

These other works can include fashion, like shoulder pads of the eighties, as well as objects of pop culture, like the comic books of the fifties! We’ll look at lots of eye candy while expanding our understanding of architectural styles and Chicago history. It’s a very visual and interactive tour.

Most of all, we’ll understand architectural style’s deeper connections with history. And we’ll consider how the advancements in technology and engineering have shaped buildings. This is the foundation of a Chicago architecture tour.

The fun and creative educational approach of this Chicago architecture walking tour makes it unlike any other architecture tour in the city.  You won’t be bogged down with dates and names with us, but we do hope to introduce you to new ideas on how to look at architecture.

And the tour is “the best” for Detours-minded folks, whether they’re locals and visitors. You will learn about various architectural styles and the buildings themselves are the best teachers.

Have you been on the architectural boat tour? This would be your next step for curious folks who want a deeper understanding of Chicago architecture (or consider the “Loop Interior Architecture Walking Tour”).

Our architecture walking tour goes south of the Michigan Avenue bridge. This is a route where many people walk, but rarely look up. We conclude at the contemporary playground of Maggie Daley Park.


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, 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!

Got a time conflict? Consider our Loop Interior Architecture Walking Tour with Pedway.

This Chicago architecture walking tour is also available as a private tour, a fun corporate event or team-building experience.


1.5 Hours


.6 Miles



  • Days & Times

  • --


  • Chicago’s underground layers
  • Michigan Avenue Bridge
  • The gold-topped Carbide and Carbon Building
  • The massive Mies van der Rohe’s Illinois Center
  • Jeanne Gang's famous Aqua Tower
  • The corporate naturalism of Maggie Daley Park

Stories & Ideas

  • Fort Dearborn and early Chicago
  • The Chicago School of Architecture
  • Art Deco and the Roaring ’20s
  • Mechanization and the spirit of Modernist architecture
  • The fun shapes of Postmodern forms
  • The latest trends in city living

Tour Includes

  • Engaging tour guide commentary
  • Special gifts
  • Discounted flat-rate parking at Grant Park North Garage ($15)

Tour Location

This walking tour begins outside Fannie May Candies, 343 N Michigan Ave.
We end inside Maggie Daley Park, 337 E. Randolph St.

Book Now


Call: 312.350.1131
E-Mail: [email protected]