Small Group Walking Tour of Chicago The Loop

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.

1. 1

   The Rookery Building

   5 min

   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.

2. 2

   Chicago Board Of Trade Building

   Pass by

   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.

3. 3

   Calder’s Flamingo

   Pass by

   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.

4. 4

   Route 66

   Pass by

   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.

5. 5

   The Art Institute of Chicago

   Pass by

   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.

6. 6

   Millennium Park

   Pass by

   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.

• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Not recommended for travelers with poor cardiovascular health
• Travelers should have at least a moderate level of physical fitness

For a full refund, cancel at least 24 hours before the scheduled departure time.