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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) 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.

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

Loop Interior Architecture Tour

Loop tour marquetteThis 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.

South Side Hidden Highlights Driving Tour

university of chicago campus architecture walking tourExperience 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 Highlights: Detour 101 Driving Tour

chicago highlights 101 riverFor first-time visitors to Chicago, especially those with a tight schedule, this is the private tour of Chicago for you. The tour views primary tourist attractions like 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 power as a hub for communications and industry, and its magnificent architecture.

Chicago Jazz, Blues & Beyond Driving Tour

Small group JBB
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.

More Small Group Private Tour Options

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

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

Some of our highly qualified Chicago Detours tour guides have fluency in French and Italian. These guides 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]