The Art of a City, Downtown Chicago Guided Walking Tour (Semi-Private)

This 2.5-hour small-group walking tour (12 guests max) is perfect for exploring Chicago’s monumental public art up close—without getting lost in the crowds.

Chicago’s world-famous skyline tells only half the story. Scattered through downtown are masterpieces by Picasso, Chagall, Miró, and Kapoor, transforming the city into an open-air museum. After the Great Fire of 1871, Chicago rebuilt itself as a global architectural powerhouse, but its public art—often hiding in plain sight—adds color, depth, and character to the “City of Big Shoulders.”

Begin at Cloud Gate—Anish Kapoor’s gleaming “Bean” that reflects the skyline—and explore works of public art that define Chicago’s streets. From towering steel sculptures to vibrant mosaics and surreal installations, discover how some of the 20th century’s greatest artists left their mark on the city. Along the way, marvel at The Rookery, a stunning 19th-century skyscraper with a Frank Lloyd Wright-designed lobby, and gaze up at the soaring Willis Tower, once the tallest building in the world.

Whether you’re drawn to abstract giants or intricate murals, this tour unveils the bold artistic visions that make Chicago’s downtown an ever-evolving canvas.