Small Group Private Tours of Chicago
For a luxury private tour of Chicago, we offer 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 either foot or bus. For groups of nine or more, please see our many Large Private Group Tour options.
For a small group private tour, you will travel via sedan, SUV or limousine to tour 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 tour of Chicago an unforgettable experience.
With our green ethos in mind, we try to use Tesla Model S electric cars for 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.
Because of the small and intimate nature of private tours for few guests, these are designed for the high-end traveler. VIP guests see downtown Chicago highlights and also the best of Chicago neighborhoods.
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 tour experiences start at $250 for a two-hour walking tour.
Please see a few of our 10+ private tour options below. Some of our Large Private Group Tours of Chicago can be customized for smaller groups as well.
Transportation for Your Private Tour
- By foot
- Luxury Tesla Model S electric sedan (maximum 3 guests)
- SUV (maximum 5 guests)
- Limousine (maximum 8 guests)
Chicago Private Tour Options
Loop Interior Architecture Walking Tour
This 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 rates as one of the best Chicago architecture walking tours.
South Side Highlights Driving Tour
Experience 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.
1893 Chicago World’s Fair Tour with Bars
Chicago Neighborhoods & Cultural Diversity Bus Tour
Loop Interior Architecture Walking Tour for Private Groups
Chicago 101 Driving Tour
For first-time visitors to Chicago, especially those with a tight schedule, this is the private tour of Chicago for you. The tour stops at 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.
Jazz, Blues & Beyond Driving Tour
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.
Chicago Highlights Tour by Bus: Detour 101
Chicago Jazz, Blues and Beyond Bus Tour
Combine a Chicago blues tour with a Chicago jazz history tour. Then throw in some perceptive ideas about cultural history and architecture, along with a blues harmonica lesson. Put them all together and you’ll end up with this unforgettable group tour.
Some of our highly qualified Chicago Detours tour guides have fluency in French and Italian. We can also give referrals for tour guides in other languages. Please call us at 312.350.1131.