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Best Architecture Walking Tour for Design Lovers – UChicago Alumni

A creative tour of Chicago architecture designed for curious people.

Special for the University of Chicago Alumni Association, this unique walking tour of downtown asks the big questions, like “What does Michael Jackson’s Thriller have to do with the design of a post-modern skyscraper? Or Andy Warhol’s soup cans with modernism?” The Architecture Walking Tour for Design Lovers is a creative tour of Chicago architecture. We designed it for curious people, like you and your fellow University of Chicago alumni.

NOTE: We are sold-out however we do have availability for our public “Best Architecture Walking Tour for Design Lovers” at 3:30pm. Please call us to reserve with your alumni discount. Hope you’ll join us!


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 an age. Styles in creations like architecture, graphic design, fashion design and pop culture have similar qualities when they come from the same era. 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 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. This best architectural walking tour appeals to both Chicago locals and visitors. People well-versed in art history will enjoy it, as well as tour guests new to looking at art and architecture. You will learn about various architectural styles, both by looking at buildings in front of us and at images and video on shared iPads.

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!

Chicago Detours Guide and UChicago alum Alex Bean will lead this walking tour. Our events with UChicago alumni sell out quickly. This is limited to 14 guests. We advise you to book asap if interested! 

If you can’t make it on this date, please consider our other UChicago Alumni Association tours we are offering:

We hope you’ll join us. You’ll get to meet the ever interesting community of UChicago alumni! Book your tour now as our events with the University of Chicago Alumni Club have all sold out.


1.5 Hours


.5 Miles



  • Days & Times

  • Saturday, September 14th
    10:00 am, 12:00pm, & 1:30pm


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

Stories & Ideas

  • Fort Dearborn and the “simple life”
  • Chicago School of Architecture
  • Art Deco and the Roaring ’20s
  • Mechanization and the spirit of modernist architecture
  • The fun shapes of post-modern forms
  • The latest trends in city evolution and living

Tour Includes

  • Shared iPads with historic photos and video clips
  • Engaging tour guide commentary
  • Special gifts
  • Discounted flat-rate parking at Grant Park North Garage ($15)

Tour Location

This walking tour begins inside 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]