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Chicago Private Walking Tours with an Expert Tour Guide

Chicago Private Tours and Experiences Hosted by Local Experts

Private Walking Tours in Chicago with an Expert Tour Guide 


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
(4.83) 125 Reviews

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

The finest way to experience to experience a museum is to have an expert right next to your right elbow. That Expert spent years training in art history and also has a deep commitment—believing that art is for the public and deeply appreciates the public’s experience of art. So imagine a person with a PhD who cares as much about teaching as your favorite grade school teacher and then wrap that person up into one being, who will spend time with you interpreting what you see, widening your experience of the world, and literally building new ways to experience that museum, the artists, and the art. That is what Context Tour guides do—no matter in what country or city. And when it comes to the Chicago Institute of art, the Context Tour guides are fantastic. And at the top of the list for my family, is Sarah C. We spent three hours with Sarah C as our guide. She was phenomenal—smart, completely well versed as an art historian, and also empathic, warm, delightful, and comfortable with all ages, Sarah is thrilled by any interest you showed in any painting and had more to add to your experience. I am absolutely certain that all Context Tour guides are terrific, because we have used them in cities and countries throughout Europe and the United States. But I would say that the finest Context Tour guide we have ever had is Sarah C. Context Tour’s will never disappoint. And if you are fortunate enough to have Sarah C as your guide at the Chicago Institute of Art, you are in for the experience of a lifetime.!! Bravo Context!
Sarah was outstanding. She has extensive knowledge about the collection of art in the museum as well as the architecture of the building itself. She guided us through several key periods in art history while highlighting the artist life as well as talking in detail about the paintings and techniques used. She brought the art work and the artist to life for all us. I would highly recommend her. Best Debra Weninger
Wonderful. Even with a decidedly dreary Chicago afternoon, we were able to see so many of the hidden gems in downtown Chicago. Our guide was wonderfully knowledgeable. Would recommend to everyone to take this tour when visiting Chicago.
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