Chicago Tours and Experiences See what others overlook. Understand what others don't.
Famous for its skyscrapers, Al Capone, and the World's Fair, the Windy City offers so much more.
Chicago Private Walking Tours
Context Travel Chicago Tours
From the ashes of the Great Chicago Fire of 1871 rose a city determined to rebuild with grandeur. This spirit is evident in Chicago's architecture, its vibrant arts scene, and the diverse communities that form its cultural backbone. Chicago's history is a narrative of rebirth, innovation, and the integration of various cultural influences, making it a living museum of human endeavor and creativity.
Dive into Chicago with our Unique Experiences:
- Chicago Architecture Tour: Embark on a walking tour of Chicago that is nothing short of a journey through time. Led by a knowledgeable Chicago tour guide, architect, or historian, this tour explores the architectural diversity from the ornate Beaux-Arts style to the stark lines of Brutalism. You'll stand in awe at the Willis Tower, once the tallest building in the world, and marvel at the intricate details of the Chicago Board of Trade Building. This Chicago tour isn't just about buildings; it's about understanding how architecture reflects the city's growth, its economic booms, and its social changes.
- Art Institute of Chicago Tour with Skip-the-Line Tickets: Art and history intertwine in this exclusive tour where you bypass the lines to dive straight into one of the world's finest art collections. A Chicago tour guide who's also an art aficionado will lead you through millennia of human creativity, from the Impressionist masterpieces of Monet and Renoir to the groundbreaking American art movements. This tour provides insights into how Chicago has been a cradle for art, influencing and being influenced by artists from around the globe.
- Architecture of Chicago Audio Guide: For those who prefer to explore at their own pace, our audio guide offers an in-depth look at Chicago's architectural landmarks. This self-guided Chicago tour allows you to delve into the stories behind structures like the Frank Lloyd Wright's Robie House or the modernist marvels in Millennium Park. With expert commentary, this guide becomes your personal Chicago tour guide, enriching your understanding of how each building contributes to the city's narrative.
Each of these experiences with Context Travel is designed not just to show you Chicago but to let you feel its heartbeat, understand its evolution, and appreciate the layers of culture and history that define this dynamic city. Whether you're an architecture enthusiast, an art lover, or simply curious about urban development, Chicago offers endless inspiration. Join us to uncover the stories etched in its streets, buildings, and galleries, guided by those who know its soul best.
What Context Chicago Travelers Say
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146 Reviews
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Joe was an incredible storyteller about the art—we learned so much, made the art very accessible, tied the art to its context including connections to music and film, and was delightful to be with . We would highly recommend Joe!!
Rachel
May 17, 2025
Sally is an outstanding guide! We were lucky to be with her for the architecture tour and the art institute tour. She was so organized, informative, and charming. She told us interesting stories about all the major figures in Chicago’s history who contributed to the buildings and the culture of the city. And we really learned so much! I have already recommended Context Chicago to several friends, and told them they must request Sally. She is the absolute best!!! We will be back and will book again! Thank you!
Melissa
Apr 27, 2025
loved going inside the buildings and seeing the beauty. Sally was very knowledgeable about the history of the buildings and Chicago. A pleasure!
Kymberly
Apr 26, 2025