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Chicago Architecture Crash Course Walking Tour

Chicago architecture and pop culture.
Starts and ends close to 40+ hotels and offices.

What does Michael Jackson’s Thriller have to do with the design of a skyscraper? How are Andy Warhol’s soup can paintings mirrored in office buildings? Discover the answers on the “Chicago Architecture Crash Course Walking Tour.” This creative tour considers building design from multiple angles, including pop culture.

Has your group been on the architectural boat tour, perhaps with the Chicago Architecture Center? This would be your next step for curious folks who want a deeper understanding of Chicago architecture with a professional tour guide.

This tour is perfect for private groups located near the Michigan Avenue Bridge. Because of its central location and condensed duration of 90 minutes, this walking tour is perfect for:

  • A post-meeting experience at one of the nearby hotels or office buildings.
  • Before a group dinner nearby
  • After an architectural river cruise, since most of them end right at the Michigan Avenue Bridge.


On this tour, your private group 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. This hour-and-a-half-long tour is a very visual and interactive experience for private groups.

Most of all, your private tour guests will understand architectural style’s deeper connections with history. And they will consider how the advancements in technology and engineering have shaped buildings. This means your tour guide goes beyond dates and names. Chicago Detours likes to introduce private groups to new ideas about looking at architecture. Guests learn about various architectural styles, both by looking at buildings in front of us and at images and video on shared iPads.

The fun and creative educational approach of this Chicago architecture walking tour makes it unlike any other architecture tour in the city. This private architectural walking tour appeals to both Chicago local corporate groups and those that are visiting Chicago for conferences and meetings. We also work with family and friend groups for our private group tours!

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, which is just next to Millennium Park.


Who wants to listen to a volunteer tour docent rambling a bunch of memorized dates and names? Not us! Our expert Chicago 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!

This Chicago architecture walking tour is also available as a public tour for eight or fewer guests, and is popular for corporate team building events.

As you decide on a private group tour of Chicago, this quick guide may help you understand if Chicago Detours is the right tour company for your special event.


1.5 Hours


0.5 Miles


  • 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

Tour Location

Get More Info

Get More Info


Call: 312.350.1131
E-Mail: [email protected]