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) 107 Reviews

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My brother-in-law, husband, and I took the Art Institute of Chicago Tour with Sally. We were pleased we had selected the skip-the-line ticket option because that allowed Sally to take us immediately to exhibits and artifacts that would later be flooded with throngs of people on the Memorial Day weekend. We were most pleased with the narrative structure of Sally’s tour, which was built around major Chicago collectors and donors to the Art Institute. We learned about the purpose of the building when it was constructed for the Columbian Exposition, its evolution into the Art Institute, and how the collection was built. Sally was impeccably organized and well-prepared. She carried a binder containing documents she had curated specifically for the tour and used them efficiently throughout. Her knowledge is prodigious, and she demonstrated it as we moved efficiently from painting to painting, style to style, artist to artist. She provided us with what felt like a graduate seminar without being didactic. Along the way, she helped us see differences in the various schools of art in terms not only of technique but also in terms of content. She didn’t waste a single moment of the available time. Throughout, she referenced information that she had given us earlier in the tour that allowed us to follow a complex verbal and visual narrative that wove together the history of the museum and its collections, the key players in building that collection, and art history. Although the tour was whirlwind, it never felt rushed. We saw the jewels of the collection as well as pieces that were less famous but demonstrated important techniques and evolutions in style within the work individual artists and the influences of artists on one another. We learned to compare and contrast styles, to recognize hallmarks of particular artists, and the history of individual paintings. The tour was invigorating, and we were grateful that we had Sally to guide the experience.
Wonderful tour. Joe made sure to address our interests and more. He shared interesting insights along the way. The tour certainly helped us make the most of our 3 hours.
Extremely knowledgeable and able to talk about any of the art on exhibit. Very accommodating to what we wanted to see (as opposed to a fixed tour).
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