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Chicago Walking Tour: Prohibition Era Legacy
4.9
99 Ratings
Chicago
Stroll through the streets of Chicago to admire the beauty and heritage from the Prohibition Era. Discover the stunning architecture, iconic landmarks (both historic and modern), and the city’s top attractions as you explore on foot.
Stroll through the streets of Chicago to admire the beauty and heritage from the Prohibition Era. Discover the stunning architecture, iconic landmarks (both historic and modern), and the city’s top attractions 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 please note that this tour covers about 4.8 km (3 miles) of walking.
- 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.
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
4.9
(99 Ratings)
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Margaret_c
Dec 22, 2025
Worth it!! - Dash was an awesome tour guide!! He took us to so many beautiful places around Chicago! I would definitely recommend, and would do it again myself!
Review provided by Viator
Mckenzie_t
Nov 8, 2025
Amazing " Had a blast " - Dave was amazing! I’ll most definitely book this tour again if I go with family or friends so they can experience the rich history and architecture of Chicago. My favorite stop was the old Chicago library — the architecture inside was absolutely stunning!
Review provided by Viator
716mckenziet
Nov 8, 2025
Amazing experience - Dave was amazing. I would most definitely book another tour with him . I loved learning about Chicago history and architect
Review provided by Tripadvisor
Valg872
Nov 8, 2025
Recommended tour! - Rich was great! The tour was well organized and his communication was prompt and helpful. We saw iconic Chicago sites as well as hidden gems! Highly recommend!
Review provided by Tripadvisor
Dianahp1000jo
Nov 7, 2025
Well done and well spent morning!! - Amazing!! Well paced and interesting!! Garrets popcorn a nice treat too! Rich was knowledgeable about the buildings! Favorite was the cultural museum
Review provided by Tripadvisor
Phillip_b
Oct 14, 2025
Dash Around Chicago With Dash - Energetic, informative and engaging tour guide. Kept our attention the entire 2 hours.
Open to questions and was prepared with interesting details.
Review provided by Viator
Paulette_j
Sep 26, 2025
Remarkable Walking Tour! - This 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!
Review provided by Viator
Christinee_k
Sep 5, 2025
Great intro to Chicago - Lots of walking, Dash is a very interesting and dynamic tour guide. Loved it!! Get a great idea of Chicago past & present.
Review provided by Viator
Kristinbh5550by
Jun 25, 2025
Good introduction to Chicago! - A 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!
Review provided by Tripadvisor
I586ewjohnf
May 29, 2025
A Dash through architecture - Dash 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.
Review provided by Tripadvisor
