Chicago Downtown Walk: History, Mystery, Comedy, Tragedy
46 Ratings
Embark on a profound, downtown walk-around in Chicago to uncover incredible stories and secrets of the city. Discover the history, mystery, comedy, and tragedy that shaped this Great Big Onion Town.
Duration: 2 hours
Cancellation: 1 day learn more
  • Chagall’s Four Seasons - Oogle your eyes over the most marvelous mosaic mural by the renowned Marc Chagall as we discover some of Chicago’s most incredible feats.
What's Included
  • Keepsakes
Additional Information

Begin a deep, urban exploration, to unveil the astounding tales and hidden secrets of the city on this essential urban experience! During our circular tour of ‘Da Loop’, we will delve into the complexities of this impressive Big Onion Town, popping in and out of remarkable structures, appreciating magnificent art and designs in the process as we discover their origins. Look forward to a captivating, amusing and revelation-filled journey of the day through my beloved home, Chicago.

  • Please bear in mind that this tour is an adventurous 2-hour, 2-mile, indoor/outdoor, downstairs/upstairs, elevator/escalator experience.
1 N Dearborn St
North Dearborn Street
Meet your guide under the RED "1" ROOF ENTRANCE of the 1 NORTH DEARBORN BUILDING located between Washington and Madison Streets, just beside the Sweetgreen, bus stop and Blue Line station. Look for the guy with a RED, WHITE and BLUE BACKPACK.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(46 Ratings)
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Mar 29, 2024
Best walking tour in Chicago - Colin was an outstanding tour guide! You can tell his enthusiasm for Chicago history! Very thoughtful, informative and interesting tour. Great value, meeting point was easy to find. Highly recommend this tour, best walking tour in Chicago!
Review provided by Viator
Mar 29, 2024
Day in Chicago - Great tour for our family. Colin provided a nice walk around downtown, with stops both indoors and outside. Little known insights and stories made it an enjoyable time for adults and children.
Review provided by Tripadvisor
Mar 26, 2024
Fantastic tour - Superb tour. Accessible, amusing, well-paced, interactive. My kids joined the tour and loved it. Would recommend. Thanks Colin!
Review provided by Tripadvisor
Mar 23, 2024
Brilliant tour with Colin - This was a great tour with Colin, he was so knowledgeable about Chicago- history, interesting facts & anecdotes. He took us to some beautiful buildings which we would never had discovered on our own. We very much enjoyed his company & chats - lovely guy Would definitely recommend this tour.
Review provided by Tripadvisor
Mar 22, 2024
Highly recommend! - Colin was very knowledgeable and fun. I was on a mobility scooter and he did a great job making sure I didn’t drive into potholes and had access to all of the places we visited.
Review provided by Tripadvisor
Mar 18, 2024
Two hours well-spent! - Colin did a great job of keeping the entire family interested on the tour. I really appreciated his story-telling skills, with a few accents peppered in occasionally. Highly recommend!
Review provided by Tripadvisor
Mar 15, 2024
Great walking tour! - Colin was funny, courteous, and knowledgeable. His tour includes spots that a tourist wouldn’t likely know about. Highly recommend!
Review provided by Tripadvisor
Jan 11, 2024
Interesting and lively intro to Chicago - Great introduction to the city, with plenty of interesting historical bits and tours of beautiful architectural spots. Colin is a great guide, keeps it lively and interesting throughout the walk. Would definitely recommend.
Review provided by Tripadvisor
Dec 17, 2023
Fascinating insight into the city - I’ve been on several Chicago walking tours. I learned so much interesting history and saw the inside of so many gorgeous buildings. Colin is personable, funny and knowledgeable
Review provided by Tripadvisor
Nov 18, 2023
Colin gives amazing tours of Chicago— check out his walking tour if you’re visiting! - Colin did an amazing job of sharing interesting facts about Chicago and showing us inside some places we never would’ve known to check out. He has a great combination of knowledge, humor, and fun that made the tour incredible. Highly recommend booking a tour with Colin if you’re interested he Chicago area and want to learn more about this amazing city!
Review provided by Tripadvisor
Select Date and Tickets
up to 12 guests
April 2024