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
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100 Reviews
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As with all our many Context tours, we had an outstanding tour of the Art Institute! It was our first time trying out Context tours in the US and I would do it again. Regarding the guide, Samantha is a real gem. She picked an interesting and cohesive throughline with which to approach an appropriate slice of the enormous collection for our 3+ hour tour. She understood a lot about the art itself, but also discussed the local history behind the museum and these acquisitions. We thought it was excellent and she was a wealth of information and also able to answer any questions that came up. We were impressed with yet another Context guide.
Courtney
May. 15, 2024
We tremendously enjoyed our tour with Sally. She has a wealth of historical knowledge not only of Chicago but of the European & American art worlds. We touched upon architecture a bit, artists’, collectors, & benefactors’ lives and the intricacies of the art itself. We highly recommend Sally.
Mary
May. 9, 2024
Sally is fantastic! She is not only incredibly knowledgeable but she is also really fun. She shared great stories, trivia (you want her on your team) and anecdotes that really brought the art and the tour to life. We have been to AIC many, many times but this was by far the best experience yet.
Thank You Sally!
Su
May. 6, 2024