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Chicago Highlights 101 Driving Tour (1-7 guests)

The best tour for curious people to discover Chicago's bold character.

This Chicago highlights driving tour brings together gorgeous sights, historic architecture, and fascinating stories from history in one professionally-guided experience. Your tour guide will point out Chicago’s best and beautiful architectural landmarks and their backstories in downtown and beyond on this driving tour, which was featured in the Chicago Reader’s Annual Gift Guide. For larger groups of 8-375 tour guests, see our Highlights Detour 101 Bus Tour. For 7 guests or less, keep reading!


Your private Chicago highlights tour will include the broad overview of Chicago architecture and history as told from an insider’s perspective. Using luxury transport with a licensed chauffeur, your professional tour guide will show you a grand view of the magnificent Chicago skyline from Museum Campus. Then you’ll see the city’s varied architectural masterpieces, like historic skyscrapers, grand mansions, and modernist buildings. All the while, your passionate and knowledgeable tour guide will share perspectives on how the city has evolved over history.

You’ll learn about roots of Chicago industry, the Great Chicago Fire of 1871, and the 1893 World’s Columbian Exposition. Chicago had incredible growth at the turn of the 20th century as it became a hub for communications, retail, and heavy industry. Your private tour will see magnificent architecture from that era up to the present day. This private group highlights tour goes beyond names and dates. Your guide will delve into stories and personalities to add context to your experience of Chicago.


Want a custom tour? The tour is two hours, and we can extend it to three or four hours. You and your tour guests can add a downtown walking tour or explore a Chicago neighborhood. You could also take a break with your guide for coffee at a cafe’ in a historic building, or stop for lunch for classic Chicago fare like a hot dog or breaded steak sandwich.

For this small group private tour, you will travel via sedan or SUV depending on your group size and preference. With our green ethos in mind, we try to use Tesla Model S electric cars for tours by sedan. These depend on availability. If not available, a different luxury sedan will provide comparable comfort.

Because of the small and intimate nature of this small-group private tours, this outing is designed for high-end travelers.

The interactive dynamic and off-the-beaten path angle of these tours appeal to a smart, well-traveled clientele, especially those who want culturally enriching activities and experiences with personal touches. A highly trained, educated tour guide with a passion for the city’s stories, landscapes, and architecture will make your tour of Chicago an unforgettable experience.


Book with us and you get both a private tour guide and licensed chauffeur! This allows your guide to focus on sharing rich details of Chicago’s architecture and history. You can also easily deboard with the tour guide for more up-close looks inside Chicago buildings, which make for amazing photo opps. Read more about our expert Chicago tour guides here.

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 downtown and in Chicago neighborhoods!

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






  • Skyline view from Museum Campus
  • The historic, castle-like Water Tower
  • Flowers along the Magnificent Mile shopping district
  • Early and contemporary skyscrapers
  • Extensive lakefront beaches and parks
  • The famous "Bean" and more public art

Stories & Ideas

  • Why Chicago is so famous for architecture
  • The 1893 World’s Fair
  • Chicago’s industrial history
  • Waterways to railroads to highways
  • Contemporary city life in Chicago
  • Big ideas in understanding the character of Chicago


Tour Includes

  • Transport via luxury sedan (max. 3 guests) or SUV (max. 5 guests). For larger SUV (max. 7 guests), call 312.350.1131 to request.
  • Licensed chauffeur
  • Professional tour guide
  • Special gifts
  • Pick-up and drop-off at downtown hotel, restaurant or other site

Tour Location

Any downtown location as defined by east of S. Wacker, south of Division Street and north of Roosevelt Road. To have a tour guide meet guests within city limits but outside of downtown is an additional flat rate (contact us for more information).

Book Now


Call: 312.350.1131
E-Mail: [email protected]