Chicago Prohibition & Architecture Tour: Hidden History Walk
Overview
Available languages
2 hours 30 minutes
Mobile ticket
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 along the way as you explore on foot.
Additional Info
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
Suitable for all physical fitness levels
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.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
Get tips on more sights, activities, and places to eat during your stay.
Enjoy Chicago-style popcorn
Discover architectural gems like Jewelers Building and London House
Join a friendly, local English-speaking guide on a walking tour.
Stroll the Chicago Riverwalk with stunning skyline views
See the Chicago Theater, Wrigley Building, and Tribune Tower.
Conclude at Millennium Park and the iconic Bean sculpture
Additional Food & Drink
Tips/gratuities for your guide
What To Expect
The Chicago Theatre
We begin at the iconic Chicago Theater marquee, then explore the city.
Chicago Pedway
Weather permitting, we’ll explore the Chicago Pedway, a network of underground tunnels used by locals and commuters.
Options
Small Group Tour
Private Tour
Reviews
93 reviews
Total reviews and rating from Viator & Tripadvisor
Dash Around Chicago With Dash
Phillip B,
Oct 14, 2025
- Review from Viator
5.00Energetic, informative and engaging tour guide. Kept our attention the entire 2 hours. Open to questions and was prepared with interesting details.
Remarkable Walking Tour!
Paulette J,
Sep 26, 2025
- Review from Viator
5.00This was an absolutely amazing walking tour of Chicago! The tour guide, Dash, made the architectural tour so much fun, and so very interesting! Dash knows so very much about buildings and architecture in Chicago. He took us inside and outside some of the most amazing buildings in Chicago filling us with intricate details. Dash even treated us to a delicious Chicago Brownie, which was created for the first Chicago World’s Fair. This tour makes you appreciate Chicago even more!
Great intro to Chicago
ChristineE K,
Sep 5, 2025
- Review from Viator
5.00Lots of walking, Dash is a very interesting and dynamic tour guide. Loved it!! Get a great idea of Chicago past & present.
Good introduction to Chicago!
kristinbH5550BY,
Jun 25, 2025
- Review from Tripadvisor
5.00A great way to see parts of the city we would not have thought about! It provided a good overview of Chicago history. Our guide, Dash, was wonderful!
A Dash through architecture
I586EWjohnf,
May 29, 2025
- Review from Tripadvisor
5.00Dash was our guide, and his knowledge and personality made this an amazing tour. He was eager to share both historical notes, and context that made Chicago’s amazing architectural history so unique. I lived in the city for 18 years and learned so much with him. Thanks for a great tour.
Great Tour with Dash
Fearless18713083259,
May 27, 2025
- Review from Tripadvisor
5.00Incredible tour, highlighted by guide Dash. He has an infectious enthusiasm for the history of the city and getting to see things from the ground and getting inside of the buildings really makes the stories come alive. 2.5 hours didn't seem like nearly enough time to cover everything he had to share. Can't recommend highly enough
A morning learning so much about Chicago
Helen M,
May 15, 2025
- Review from Tripadvisor
5.00Rich was such a good guide. He set a realistic pace and was helpful and informative. We had a worthwhile experience and learnt so much more than we would have on our own.
Rich is a gem!
Jennifer V,
May 5, 2025
- Review from Viator
5.00We loved our tour with Rich, it felt like walking through town with an old friend. Highly recommend!
A great experience with a great guide
Megan B,
May 3, 2025
- Review from Viator
5.00We had a great time learning about the architectural history and sights of Chicago with Rich! He was very knowledgeable and had lots of interesting details about each of the places we visited.
Don't miss this tour!
Betsy D,
Apr 27, 2025
- Review from Tripadvisor
5.00Wow!! We would have given this tour 6 stars if we could. Our tour guide, Dave, was so knowledgeable and spun the stories to weave Chicago's history so clearly for these East Coast visitors. Loved the mixture of interior and street landmarks. We learned so much and will be sure to recommend this tour to others. A true highlight activity of our visit to Chicago.
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Operated by Intrepid Urban Adventures - USA