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Small Group Private Tours

Just you, your group of eight or less and a professional tour guide


Small Group Private Tours of Chicago

For a luxury private tour of Chicago, we offer large (nine to 425 guests) groups tours and also small private group tours for one to eight guests for family, friends, and corporate clients. Our tours of interior architecture, historic bars, and Chicago neighborhoods are by foot, sedan or SUV. For groups of nine or more, please see our many Large Chicago Private Group Tour options. We can also create custom tours for small private groups.

A small group private tour is an intimate way to experience Chicago’s best architecture, history and culture. A highly trained, educated tour guide with a passion for the city’s stories, landscapes, and architecture will make your Chicago private tour an unforgettable experience.

Contact us for our Chicago Detours Private Tour Catalog by calling 312.350.1131.

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. Rates for these premium private tour experiences start at $250 for a two-hour walking tour.

Please see a few of our 10+ private tour options below.

Chicago Private Tours for Small Groups

Make Your Own Detour (1-5 guests)

bar tour mag mile tour group small business chicago

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This spontaneous custom tour designs an experience to suit your group’s unique interests. At check-in for your private tour, each guest fills out a brief form to gauge their unique interests. Your expert tour guide will take a few moments to carefully create a tour itinerary for your group based on their input, and determine the best way to get around (on foot, via the ‘L,’ or even a ride-share). Then you are off on your Detour!

Chicago Highlights: Detour 101 Driving Tour

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This 2-hour driving tour views Chicago’s most popular tourist attractions from a fun and engaging angle. You’ll see Navy Pier, Millennium Park, Lincoln Park, Magnificent Mile, Museum Campus, the Water Tower, the lakefront, and downtown’s skyline. You’ll learn about the Great Chicago Fire, the growth of Chicago around the turn of the last century, its role as an industrial and communications center, and why it is famous for architecture.

Loop Interior Architecture Tour

Loop tour marquette custom tours private group toursThis walking tour of interiors and the underground Pedway System gives you a creative overview of Chicago history and architecture. Stops include Chicago’s Modernist architecture, the grand Marshall Field’s department store, a church in a skyscraper, and the “Chicago Picasso” sculpture. The infamous Block 37 and the spectacular Tiffany mosaics at the Cultural Center are also included. It is ranked Chicago’s #1 Cultural Tour on TripAdvisor.

Architecture of Money and Power

LaSalle Street Chicago Financial District Rookery

This walking tour in the heart of Chicago’s financial district will take you and your private group to discover opulent architecture and secret stories. We’ll visit what was the largest and most technologically advanced building of the 1930s, and consider the background of skyscrapers as a symbol of financial power.

South Side Hidden Highlights Driving Tour

university of chicago campus architecture walking tour custom toursExperience the area of the 1893 World’s Columbian Exposition, the beautiful Chicago lakefront, and the University of Chicago campus in Hyde Park. You’ll view the exterior of Frank Lloyd Wright’s famous Robie House, as well as some of his lesser-known commissions. President Obama’s house can be included, as well as sites significant to jazz and blues history. On this tour, you and your guests will better understand Chicago’s most historic and most overlooked neighborhoods of the South Side.

Chicago Jazz, Blues & Beyond Driving Tour

Small group JBB custom tours
This daytime tour goes to neighborhoods from the North to the South Sides and delves into the people, politics and culture that have made Chicago a hotbed for musical innovation. Ballrooms, recording studios and former clubs are the highlights. Depending on time of day, you can even enter into a club where Louis Armstrong once played, to see the original stage and mural from the Jazz Age.

Custom Tour Options for Small Groups

Some of our Large Private Group Tours of Chicago can be customized for smaller groups as well. Contact us for details on how these custom tour may be be tailored to your small private group. Here are just a few of the Chicago private tours available:

Transportation for Your Private Tour

  • By foot
  • Luxury Tesla Model S electric sedan (maximum 3 guests)
  • SUV (maximum 5 guests)
  • Limousine (maximum 8 guests)

With our green ethos in mind, we try to use Tesla Model S electric cars for our Chicago private tours by car. Because we work with a small business for the Tesla rentals, this extra bonus for your private tour does depend on availability.

Foreign Languages

Our interactive city tours are also available in Italian. Tour guide and company founder Amanda is fluent in Italian and can do private walking tours or tours by car. We can also give referrals for tour guides in other languages for private tours. Please call us at 312.350.1131.


Call: 312.350.1131
E-Mail: [email protected]