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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.
About this activity
- Free cancellation
- Cancel up to 24 hours in advance for a full refund
- Reserve now & pay later
- Keep your travel plans flexible — book your spot and pay nothing today.
- Duration 2.5 hours
- Check availability to see starting times
- Live tour guide
- English
- Private group available
Highlighted reviews from other travelers
Rich was a great tour guide, he was very knowledgeable and it a great tour of Chicago highlights
Our tour guide Bash was outstanding. He enthusiastically shared his love for Chicago and its history. This is a must tour for first timers to Chicago. We learned so much about the history, architecture and people who made Chicago.
Select participants and date
Itinerary
Starting location:
The Chicago Theatre
Chicago Pedway
Guided tour, Walk (20 minutes)
Chicago City Hall
Guided tour, Walk
Chicago Picasso Statue
Guided tour, Walk (10 minutes)
Chicago River
Guided tour, Walk (20 minutes)
Chicago Riverwalk
Guided tour, Walk (20 minutes)
Wrigley Building
Guided tour, Walk
The Magnificent Mile
Guided tour, Walk (10 minutes)
Millennium Park
Guided tour, Walk (20 minutes)
Cloud Gate
Guided tour, Walk
Finish at:
Millennium Park
For reference only. Itineraries are subject to change.
Highlights
- Explore Chicago’s Prohibition-era legacy and iconic architectural landmarks
- Stroll along the Riverwalk, discovering key buildings like Willis Tower
- Visit the Chicago Cultural Center and enjoy a local Chicago-style popcorn treat
- End at Millennium Park and the iconic Bean, with tips for lunch and sights
- Receive personalized attention on a small-group tour with just 12 participants
Full description
Start at the Chicago Theater, then stroll along the Riverwalk, learning about key landmarks like Marina Towers, Willis Tower, and the Jewelers Building. Discover Art Deco designs at the London House and Du Sable Bridge.
Visit the Chicago Cultural Center, a stunning architectural gem, and enjoy a local treat of Chicago-style popcorn. Learn about the Wrigley Building, Tribune Tower, and the city’s historical roots in journalism.
End at Millennium Park, home to the iconic Bean sculpture, with your guide offering great recommendations for lunch and further sights.
Includes
- Local English-speaking guide
- Popcorn tasting
- Gratuities
Meeting point
The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601
Open in Google MapsImportant information
What to bring
- Comfortable shoes
- Weather-appropriate clothing
Know before you go
- This tour is carbon neutral, operated by a B Corp certified company committed to using travel as a force for good. This Certification measures a company’s social and environmental impacts and responsible tourism practices.
- The maximum number of people on small group tour will be 16 passengers.
- This is a child-friendly walking tour. Children under the age of 6 are permitted to join this tour free of charge.
- Suitable for all ages and fitness levels, but please note that this tour covers about 4.8 km (3 miles) of walking.
- Experiences happen rain, shine, or snow. Please dress accordingly.
- 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.