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Chicago private tours and Chicago small group tours

Chicago Private and Small Group Walking 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
61 Reviews (4.82)

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

William was very well-informed and well plugged in. He was also very good company. We greatly enjoyed our tour.
Sally is a very nice person, however she is certainly not an art historian. My husband and I have used Context Travel all over Europe: Paris, Florence, Venice, London, Madrid and Lisbon. In the past, we have always been pleased by the quality of the docents. Typically, for a tour of a world class art museum, we would expect to get someone with a strong academic background in art history. For instance, when we were in Madrid, in 2019, we had a marvelous tour through the Prado, led by a young and engaging doctoral candidate. Several years earlier, in Venice, all of our tours were led by a a lovely woman who was also a doctoral candidate. Given that we had to pay for a private tour, as there do not seem to be any group tours available in Chicago, I must honestly tell you that we did not feel that we got very good value for our time and money. (By contrast, our architecture tour with William was up to snuff, and my husband will be reviewing that one as he is the architect in the family.)
Sarah is fantastic. She’s very knowledgeable and enthusiastic. We had a great time. Thank you.