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
(4.82) 113 Reviews

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Sally was a terrific guide. She was especially informative about the history of the museum in addition to the individual works we discussed.
The tour of the Art Institute was really great; I felt that we got much more out of our time at the Art Institute with Sally than we would have gotten if we had attempted to go on our own. Sally was particularly good at talking about the art and the exhibits with our kids, and managed to keep their attention through the tour. She also modified the tour along the way to take into account our interests and our energy level, which was much appreciated.
For everyone who’s already taken and enjoyed the famous Chicago architecture boat tour, this walking architecture tour is next level. William was a truly engaging and informed expert (as a practicing architect) who shared his knowledge and enthusiasm as we strolled around the south Loop area of the city and learned so much about historic Chicago architecture. If you have any interest in architecture, Chicago history, design, or public buildings, you should take this tour.
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