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Chicago Prohibition Tour: Explore Historic Streets
4.8
81 Ratings
Chicago
Tour the streets of Chicago to see the beauty and legacy left behind by the Prohibition Era. See the amazing architecture, iconic sights (both old and new), the city’s best spots and try a local sweet treat along the way as you explore on foot.
Tour the streets of Chicago to see the beauty and legacy left behind by the Prohibition Era. See the amazing architecture, iconic sights (both old and new), the city’s best spots and try a local sweet treat along the way as you explore on foot.
Duration:
2 hours, 30 minutes
Cancellation:
24 hours
Highlights
- The Chicago Theatre - Start at the renowned Chicago Theatre marquee and then venture into the city.
- Chicago Pedway - If the weather is favorable, explore the Chicago Pedway, a series of underground tunnels frequented by locals and commuters.
- City of Chicago - City Hall - Pass by the City Hall-County Building, which houses Chicago’s…
- The Chicago Theatre - Start at the renowned Chicago Theatre marquee and then venture into the city.
- Chicago Pedway - If the weather is favorable, explore the Chicago Pedway, a series of underground tunnels frequented by locals and commuters.
- City of Chicago - City Hall - Pass by the City Hall-County Building, which houses Chicago’s government and Cook County offices.
- Picasso Statue - Visit the Chicago Picasso in Daley Plaza, a 1967 installation that revolutionized public art and urban planning.
- Chicago River - Experience the local vibe as you walk by iconic buildings, enjoy breathtaking skyline views, and join the daily commute along Chicago’s main thoroughfare.
- Chicago Riverwalk - Weather permitting, take a leisurely walk along the award-winning Chicago Riverwalk, admiring views of iconic structures like Marina Towers, the Wrigley Building, and the Tribune Tower.
- Wrigley Building - Pass by the historic Wrigley Building at 400 N Michigan Ave, a landmark in the heart of Chicago.
- Tribune Tower - Continue past the Tribune Tower, a 463-foot, 36-story neo-Gothic skyscraper at 435 North Michigan Avenue.
- The Magnificent Mile - Stroll along the Magnificent Mile on North Michigan Avenue, a lively area filled with shops, restaurants, and attractions, developed as part of the 1909 Burnham Plan.
- Chicago Cultural Center - Enter the Chicago Cultural Center, a landmark where the Mayor has greeted presidents, royalty, and dignitaries.
- Millennium Park - Visit the scenic Millennium Park, home to the famous Bean sculpture. The guide will conclude the tour here, providing suggestions for nearby attractions, dining, or drinks.
- Cloud Gate - Conclude the tour at the Cloud Gate sculpture, also known as ‘The Bean,’ the highlight of Millennium Park.

What's Included
- Join a friendly, local English-speaking guide on a walking tour.
- Stroll the Chicago Riverwalk with stunning skyline views.
- Discover architectural gems like Jewelers Building and London House.
- See the Chicago Theater, Wrigley Building, and Tribune Tower.
- Conclude at Millennium Park and the iconic Bean sculpture.
-
Enjoy Chicago-style popcorn.
-…
- Join a friendly, local English-speaking guide on a walking tour.
- Stroll the Chicago Riverwalk with stunning skyline views.
- Discover architectural gems like Jewelers Building and London House.
- See the Chicago Theater, Wrigley Building, and Tribune Tower.
- Conclude at Millennium Park and the iconic Bean sculpture.
- Enjoy Chicago-style popcorn.
- Get tips on more sights, activities, and places to eat during your stay.
What's Not Included
- Additional Food & Drink
- Tips/gratuities for your guide
- Additional Food & Drink
- Tips/gratuities for your guide
Additional Information
- This is a child-friendly tour. Children under 6 join for free. Children ages 6-11 can join at the adult rate. Please inform us of any children in your party at the time of booking, using the special requirements box on the checkout page.
- Experiences happen rain, shine, or snow. Please dress accordingly.
- Suitable for all ages and fitness levels, but…
- This is a child-friendly tour. Children under 6 join for free. Children ages 6-11 can join at the adult rate. Please inform us of any children in your party at the time of booking, using the special requirements box on the checkout page.
- 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.
Location
The Chicago Theatre
North State Street
The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.8
(81 Ratings)
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David_c
Feb 1, 2025
Provided lots interesting... - Provided lots interesting details throughout the walk on rainy Friday. Knew his information and communication was very clear.
Review provided by Viator
Andreajacobsen2
Dec 29, 2024
Must do! - It was amazing. I grew up in Rockford, IL and grew up going to Chicago a few times a year. But I never knew about its rich full history and of course its beautiful architecture. I know the boat tours are popular, but I recommend doing this one instead!! Going inside the buildings and learning about its history and viewing the ceilings and interior was amazing.
Review provided by Viator
Rob_b
Nov 25, 2024
Best city tour I’ve ever had - My gf and I had the best tour with Dave. He knew so many hidden spots and all the history we were interested in. Highly highly recommend
Review provided by Viator
Sue
Oct 29, 2024
Chicago by foot in 2 1/2 hours - Our guide, Rich, was great. He enthusiastically took us on a very informative tour of beautiful buildings and sculptures. Lots of time to stop along the way for photo opportunities ( and enjoyed our chocolate and popcorn!)
Review provided by Tripadvisor
Sergio_l
Sep 9, 2024
Chicago so much to see - The former library is beautiful. The stops were informative. Overall it was the right amount of time for a walking tour.
Review provided by Viator
Sam_h
Aug 14, 2024
Really interesting tour... - Really interesting tour all of it was fascinating. Our tour guide was very knowledgeable and his enthusiasm Chicago and the tour was brilliant
Review provided by Viator
Laurasd1364wx
Jul 20, 2024
A great your! - It was a good tour! Dave is knowledge and has passion for his adopted city. I enjoyed this tour and would recommend to others!
Review provided by Tripadvisor
Jadey4646
Jul 13, 2024
Even better than playing knifey-spooney - Went on the architecture tour with Tall Dave. He was extremely knowledgeable and charismatic, and provided insight into the life of certain Chicago buildings. It was clear that he had conducted significant research into Chicago’s history. The visual aids were very helpful!
Review provided by Tripadvisor
Emilia_l
Oct 9, 2024
Curious and entertaining guide - The cultural center tour was fantastic. The explanation was educational. It was billed as a prohibition tour but the information on that topic was limited.
Review provided by Viator
Akinsiku_t
Aug 2, 2024
Tour - The tour guide was on time, patient and understanding. He was kind and accommodating.
The tour was done in a bit of a rush and we didn’t enjoy the tour as much as we could have. It was a small group of two couples- it would have been nice if we were addressed by our names too, just like it was for the other couple.
Review provided by Viator