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Chicago Highlights Detour 101 Bus Tour

The best tour to discover Chicago's bold character through its architecture and history.

This Chicago highlights tour is based on quality and not quantity. Your tour guide will point out Chicago’s best and beautiful architectural landmarks and their backstories in downtown and beyond on this bus tour.


Our mission is to share stories and places locals don’t even know. So your private Chicago highlights tour will include the broad overview of Chicago architecture and history from an insider perspective. You’ll get a grand view of the magnificent skyline of Chicago from Museum Campus and also see Chicago’s architectural masterpieces, like historic skyscrapers, grand mansions, or modernist buildings. All the while, your professional tour guide will share perspectives on how cities grow and change over history.

You’ll learn about the Great Chicago Fire of 1871 and the incredible growth of Chicago around the turn of the 20th century. The city was a hub for communications, retail, and industry. Your private tour group will see magnificent architecture from this era and up to the most recent in contemporary architecture. The private group highlights tour uses the stories behind buildings to bring meaning to your experience of Chicago. The tour is two hours, and we can extend it to three or four with some stops for interior architecture, a Chicago neighborhood, and a break for coffee or lunch.


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 Google and TripAdvisor. Many of our Chicago architecture 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 in Chicago neighborhoods and downtown!

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.


2 Hours




  • Museum Campus skyline view
  • The historic Water Tower
  • Magnificent Mile shopping district
  • Lakefront beaches and parks
  • State Street - that great street
  • Printer's Row Historic District
  • Downtown early skyscrapers

Stories & Ideas

  • The great Chicago fire
  • Turn-of-the-century life
  • Communications and industry
  • Why Chicago is so famous for architecture
  • Contemporary city living
  • Core ideas in understanding the character of Chicago

Tour Includes

  • 18- or 39-passenger coach bus for up to 3 hours
  • Engaging tour guide commentary
  • Special gifts

Tour Location

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Call: 312.350.1131
E-Mail: [email protected]