Explore Chicago with a passionate local guide on a small-group walking tour that takes you beyond the city's most recognizable landmarks. As you stroll through the heart of the city, you'll uncover fascinating stories, admire world-renowned architecture, and learn about the pivotal events that helped shape Chicago into one of the world's most influential destinations.
With a small group, you'll enjoy a relaxed and interactive experience, giving you plenty of opportunities to ask questions and connect with your guide. Along the way, you'll receive insider tips on the best places to eat, drink, and explore, helping you experience Chicago like a local long after the tour ends.
Whether you're visiting for the first time or returning to discover more, this tour offers an engaging introduction to Chicago's history, culture, and architectural heritage.
You will find us next to the Picasso statue, look for our blue umbrella!
Discover the Rookery Building, one of Chicago's most iconic historic skyscrapers. Admire its stunning architecture and step inside to see the beautiful lobby redesigned by Frank Lloyd Wright. Learn how this pioneering building helped shape modern skyscraper design and became a symbol of Chicago's architectural innovation.
Stand before the iconic Chicago Board of Trade Building, a masterpiece of Art Deco architecture and one of the city's most important financial landmarks. Learn how Chicago grew into a global trading powerhouse, discover the fascinating history of the world's first futures exchange, and admire the impressive details of one of the city's most photographed skyscrapers.
Admire Calder's Flamingo, the monumental bright-red sculpture that dominates Chicago's Federal Plaza. Discover how Alexander Calder's innovative design brought movement and color to the city's financial district while learning about Chicago's world-renowned collection of public art and its close relationship with architecture.
Stand at the official starting point of Historic Route 66, one of the world's most famous highways. Capture a photo beside the iconic "Begin Route 66" sign and discover how this legendary road became a symbol of exploration, opportunity, and the American Dream, inspiring generations of travelers from Chicago all the way to California.
See the exterior of the iconic Art Institute of Chicago, one of the world's leading art museums. Admire its impressive Beaux-Arts architecture and the famous bronze lions at its entrance while learning about the museum's rich history and the masterpieces housed inside, making it one of Chicago's most celebrated cultural institutions.
Explore the highlights of Millennium Park, Chicago's most famous urban park. Discover its striking blend of art, architecture, and green spaces while learning about the park's remarkable transformation into one of the city's top attractions. Along the way, you'll see iconic landmarks such as Cloud Gate ("The Bean"), Crown Fountain, and the Jay Pritzker Pavilion.
For a full refund, cancel at least 24 hours before the scheduled departure time.
You can cancel up to 24 hours in advance of the experience for a full refund.
Your guide to the flawless travel experience