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Chicago private tours and Chicago small group tours

Chicago Tours and Experiences Hosted by Local Experts

Famous for its skyscrapers, Al Capone, and the World's Fair, the Windy City offers so much more.
Chicago, the third largest city in the United States, is considered one of the world's foremost for architecture. Its celebrated skyline sports the Willis Tower (formerly the Sears Tower), a colossal 110-story structure, and other impressive skyscrapers like the Tribune Tower and the Monadnock Building, briefly the world's tallest when it was completed in 1893. A Midwestern hub since the early 19th century, and built up after the Great Fire of 1871, this lakeside city has become a modern cultural capital. Art, including the world-class collection at the Art Institute of Chicago, and public art sculptures by the likes of Alexander Calder permeates the streets—and soul—of the city. Immerse yourself in Chicago's culture with Context's Chicago private tours and Chicago small group tours.

Chicago Private Tours and Chicago Small Group Tours

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
88 Reviews (4.82)

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Joe was fantastic and very knowledgeable!
We had an amazing tour of the Art Institute with Sally. She was so knowledgeable about the history of the art pieces and made the experience both fun and informative. We are planning to book an architectural tour with her in the spring.
We absolutely loved our private tour with Sally! Worth every single penny. My boyfriend and I took a tour to celebrate his 28th birthday and we had such an amazing time. We learned so much and Sally is incredibly knowledgeable, fun, and FUNNY. We stopped and learned about important pieces of work that we would have otherwise just walked by without a second thought. She wove in a story/theme throughout the tour which made everything cohesive and memorable. A couple of weeks after our tour, my parents and sister went on the same tour with Sally and had the BEST time. My father is an artist and he was totally blown away. Sally is the best! We are already telling all of our friends and colleagues about her and Context Tours. If you are on the fence about going on this tour - GO. To quote my boyfriend "I wish that we could bring Sally with us to every museum we go to for the rest of our lives, it will never be the same without her."