Discover the best of Chicago’s architecture, history, and local treats on this engaging small group walking tour. Join a knowledgeable local guide and explore the city’s iconic sights and hidden gems.
- The Chicago Theatre - Our tour kicks off beneath the glittering marquee of the Chicago Theatre, a landmark featured in numerous films and TV shows, before we venture into the lively city.
- Chicago Pedway - If the weather is favorable, we’ll make our way to the Chicago Pedway. This distinctive aspect of Chicago consists of a network of underground tunnels used daily by locals and commuters, especially during the harsh Midwest winters.
- City of Chicago - City Hall - We’ll pass by the City Hall-County Building, commonly referred to as City Hall, which houses the government offices of the City of Chicago and Cook County.
- Picasso Statue - Our next stop is the Chicago Picasso sculpture by Pablo Picasso in Daley Plaza. Installed in 1967, The Picasso marked a significant shift in civic and urban planning, expanding the concept of public art beyond mere commemoration.
- Chicago River - Feel like a local as you zip past buildings and take in more stunning views. If your guide opts for a water taxi, you’ll experience the Chicago skyline from a unique vantage point, sharing the daily commute of Chicagoans.
- Chicago Riverwalk - This award-winning $108 million, 1.25-mile promenade runs along the south bank of the Chicago River downtown. Weather permitting, we’ll stroll along the Chicago Riverwalk, enjoying views of several towering buildings, including Marina Towers, the Britannica Building, and the Sears Tower (now Willis Tower).
- Wrigley Building - We’ll pass by the Wrigley Building at 400 N Michigan Ave.
- Tribune Tower - We’ll also pass by the Tribune Tower, a 463-foot-tall, 36-floor neo-Gothic skyscraper located at 435 North Michigan Avenue.
- The Magnificent Mile - We’ll stop at the Magnificent Mile, a premier commercial district in downtown Chicago. Part of the 1909 Burnham Plan of Chicago, this area was developed in the 1920s to replace an industrial and residential zone. It features numerous shops, restaurants, hotels, and attractions along North Michigan Avenue.
- Chicago Cultural Center - Step inside this Chicago Landmark building managed by the Department of Cultural Affairs. The Cultural Center serves as the city’s official reception venue, where the Mayor of Chicago has greeted presidents, royalty, diplomats, and community leaders.
- Millennium Park - Next, we’ll visit the scenic Millennium Park, home to the iconic Bean sculpture. Here, or nearby, your guide will conclude the tour and provide directions to more fantastic sights, great lunch spots, or a recommended drink venue in one of the city’s most remarkable spaces.
- Cloud Gate - Our tour concludes at Cloud Gate, a public sculpture by Indian-born British artist Anish Kapoor, which serves as the centerpiece of AT&T Plaza in Millennium Park, located in the Loop community area of Chicago.
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- Stunning river views
- Friendly local English-speaking guide
- Stroll through beautiful parks
- Tips on what else to see, do, and eat
- Discover Chicago’s incredible architecture
- Taste Chicago-style popcorn
- Pass by Chicago Theatre
- Additional Food & Drink
- Tips/gratuities for your guide
Walk Chicago to see the legacy left behind by the Prohibition Era. See the architecture, iconic sights (both old and new), and best spots and try a local sweet treat along the way.
See the gorgeous Chicago skyline and discover why this city’s architecture is among the best in the world; Enjoy some classic Chicago-style popcorn; Immerse yourself in the best of Chicago’s culture and discover the inspirations that the Prohibition Era had on the city in the 1920s; Feel the energy and life in one of Chicago’s most beautiful parks and get the iconic photo at the world-famous Bean sculpture
- This is a child-friendly tour. Children under the age of 6 are permitted to join this tour free of charge.
- Experiences happen rain, shine, or snow. Please dress accordingly.
- Suitable for all ages and fitness levels, but please note that this tour covers about 4.8 km (3 miles) of walking.
- We can accommodate vegetarian options but cannot accommodate other food allergies or dietary preferences. Please notify us in advance if you have any dietary requests.
For a full refund, cancel at least 24 hours before the scheduled departure time.