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Chicago private tours and Chicago small group tours

Chicago Tours and Experiences Hosted by Local Experts

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
95 Reviews (4.83)

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Joe gave a fabulous tour of the AIC. He was extremely knowledgeable and personable, and entertaining as well. We were happy to listen to Joe as he riffed on some of the landmark paintings, and he guided us through a well curated selection of AIC galleries that presented an outstanding cross section of major works, and also introduced us to lesser known, but important collections. Highly recommend!
William was a fantastic guide. His knowledge of Chicago’s architecture was second to none. I loved the level of detail he explained in a variety of buildings both old and modern. Hugely informative.
This was our fifth Context tour and we've come to have very high expectations of them. Colm did not disappoint! He was friendly, incredibly knowledgeable, and all around fantastic. It made our weekend.
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