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Chicago private tours and Chicago small group tours

Chicago Private and Small Group Guided Tours

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Famous for its skyscrapers, Al Capone, and the World's Fair, the Windy City offers so much more.
Chicago, the third largest city in the United States, is considered one of the world's foremost for architecture. Its celebrated skyline sports the Willis Tower (formerly the Sears Tower), a colossal 110-story structure, and other impressive skyscrapers like the Tribune Tower and the Monadnock Building, briefly the world's tallest when it was completed in 1893. A Midwestern hub since the early 19th century, and built up after the Great Fire of 1871, this lakeside city has become a modern cultural capital. Art, including the world-class collection at the Art Institute of Chicago, and public art sculptures by the likes of Alexander Calder permeates the streets—and soul—of the city. Immerse yourself in Chicago's culture with Context's Chicago private tours and Chicago small group tours.

Chicago Private Tours and Chicago Small Group Tours

Curious to learn how Chicago went from a slaughterhouse to one of the great cultural and architectural centers of the United States? Join us as we explore this amazing city with our local Chicago private guides. Our Chicago tours are designed to take you beneath the surface so that you can leave Chicago knowing about more than just a few quips about Al Capone. For first-timers we highly recommend our Chicago History Tour, which covers downtown, Millennium Park, and other attractions in the center of Chicago. If you’re like us and can spend days thinking about buildings, design, and how space is used, then we highly recommend our Chicago Architecture Tour with an Architect. Art lovers rejoice—we also offer a tour of Chicago’s Art Institute with a curator, art professor, or art historian, which is a great way to spend an afternoon. Also, did you know that Chicago has one of the world’s best collection of public art? Miro, Chagall, and others dot the downtown. So, when we’re dreaming of art we alight for the city center and take our Picasso in the Loop Tour, which is led by a local art professor and covers all the iconic pieces in the open-air gallery that is Chicago’s Loop. Or, dig deeper on our Gold Coast Tour to visit Chicago’s opulent mansions, including Louis Sullivan’s Charnley-Persky House. Still anxious about your trip or wondering how to make the most of it? Book our Welcome to Chicago experience. We’ll meet you at your accommodation when you arrive, for a 2-hour orientation chat and mini-tour of your neighborhood.
What Context Chicago Travelers Say
40 Reviews (4.8)

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

Sally was wonderful, extremely knowledgeable and we had a great experience. We highly recommend her!
Sarah provided an informative and well planned Art Institute tour for our family of four, including keeping our 8 and 10 year old girls interested and engaged. We all enjoyed our afternoon.
We so enjoyed our tour of the Art Institute of Chicago with Sally Kalmbach. She led us on an high energy few hours entertaining us not only with details about the art but how it came to be on display in Chicago. We came away with a great overview of the colorful history of Chicago and the joy of their thoughtful art collection. We only wish we could have booked a bit shorter tour - three hours is a long time on your feet when the cafe is closed due to the pandemic. Sally did a great job of directing us to benches for viewing while she continued with her stories.