Chicago private tours and Chicago small group tours

Chicago Private 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
(4.83) 125 Reviews

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Sally gave us a truly unforgettable tour filled with little-known facts and insights into the artists’ lives and their patrons/collectors. We heard and saw things we never would have on our own. We easily could have spent 4 or 5 hours with her, but sadly, the museum was closing.
Sarah was an absolute star. We had such a wonderful time chatting with her and touring the collection. I was shocked when 3 hours passed! I would 10000% recommend her to anyone looking for a personable, funny and smart as a whip tour guide.
SARAH IS IN A TIE FOR THE BEST TOUR GUIDE IVE EVER HAD. AND IVE HAD A NUMBER OF THEM. FUN, INFORMATIVE, KNOWLEDGEABLE. THE WORKS.
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