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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 private and small group guided tours.

Want more than a tour in Chicago? Talk to our expert planners about custom and multi-day options at +1 (800) 691-8328. 

Chicago Private and Guided 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 local experts. 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 other expert guide, 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
34 Reviews (4.76)

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

The instructions prior to the tour were excellent and sent at just the right time.
Sarah was a pleasure to work with. She inspired us to think about iconic paintings which enriched our experience!
Unlike in Rome, Context had some difficulty locating a guide for the Art Institute of Chicago. We had specifically requested a guide who could give a deep dive into the extensive Impressionist art housed in this museum as well some time spent on the Italian renaissance. Our first choice of guide who seemed to specialize in these areas was unavailable. Context eventually found Sally to be our guide. Sally was very warm and welcoming and a pleasure to be with. As visitors from out of state, we were seeking insights into the actual art and artists, a deeper understanding of the Impressionists. This is what I requested, and indicated online that I was NOT interested in spending a lot of time on the ‘Chicago’ history and connections of each piece. My sister, who lives in Chicago, joined us; she’s also been on Context tours before – so we have insights from two different perspectives. Sally has an affinity for the Thorne miniatures, so we started there. It was fun to watch her share her passion. My sister’s kids have read ‘The 68 Rooms’ by Marianne Malone which connects those little rooms with time travel and she LOVED it. It’d be fun to read Malone’s books with your kids and then visit these little rooms. These miniatures are NOT my passion, but it was kinda cool to see Sally so excited about them – and thankfully she highlighted only a few and then moved on (or we would have asked her to do so). Sally provided a great overview of the Chicago families that were the benefactors of the Impressionist pieces. Ms. Berthe Potter Palmer, Bartlett, Ryerson, Annie Coburn, John Singer Sargant… she shared which pieces were from which collection, how they were acquired, bought, and sold over the years. Then she’d step back and say, ‘do you want to wander around and look at the art?’ My heart dropped. This was exactly what I wasn’t looking for – but didn’t think pressing Sally for artistic insists she didn’t have would be helpful. My sister, from Chicago, did enjoy all the Chicago connections, Chicago stories, and prominent Chicago families. I had hoped to learn more about people like Monet, Manet, Renoir, Degas, Cezanne… Sally did open my eyes to an Impressionist artist I wasn’t really aware of: Mary Cassatt. I would have loved more of THAT kind of emphasis with all the Impressionist artists and their art. At the end of the tour, Sally showed us where the Italian renaissance art was – but this was neither her area of expertise nor her passion, unlike the Thorn Miniatures. PLEASE, PLEASE, PLEASE – ask for Sally if want to get a feel for Chicago’s history with the acquisition of art for the Art Institute, connections to Chicago history, and insights into Chicago’s prominent families (or a tour of Chicago, she does those too!) and especially if want to learn more about the Thorn Miniatures. She literally wrote the book on them: Mrs. Thorne's World of Miniatures by Sally Sexton Kalmbach.