Chicago Tours and Experiences

See what others overlook. Understand what others don't.

(4.85)

See all 171 reviews

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

(4.85) – 171 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.

Sally’s passion for Chicago's architecture and history made our tour of Chicago feel like a truly special experience. Sally educated us on many colorful facts about architects, the buildings, the materials, the symbolism, historical events, and provided a wealth of fascinating details to enrich our experience. Plus, she took us to the most beautiful buildings in Chicago… Highly recommend! Thank you Sally for a wonderful tour!

Michael

Dec 31, 2025

Arnold was fantastic!

Brenda

Dec 18, 2025

Joe was a wonderful guide. He was extremely knowledgeable and a joy to see the museum with!

Rebecca

Nov 30, 2025

View more reviews

Architecture of Chicago Audio Guide

Art Institute of Chicago Tour with Skip-the-Line Tickets

Chicago Architecture Tour