Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour
Recommended by 100% of travelers
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Chicago, USA
- 2 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about the city’s past. See the stunning interiors and exteriors of noteworthy buildings and leave with a comprehensive understanding of the city’s downtown.
- See art like Calder’s Flamingo and Picasso's 50 foot sculpture
- Look at Chicago Theatre and learn about the city’s greatest entertainers
- Learn about Chicago’s role in shaping the modern-day department store
- Pick the time that works for you with morning and afternoon tour options
What's Included
- All Fees and Taxes
Meeting and Pickup
Meeting point
- 1 N Dearborn St, Chicago, IL 60602, USA
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.
End point
- Chicago Cultural Center78 E Washington St, Chicago, IL 60602, USA
We will conclude our tour at the magnificent "People's Palace", The Chicago Cultural Center.
Itinerary
1
Chagall's Four Seasons
15 minutes • Admission Ticket Free
2
Marquette Building
10 minutes • Admission Ticket Free
3
Calder’s Flamingo
10 minutes • Admission Ticket Free
4
The Rookery Building
15 minutes • Admission Ticket Free
5
The Picasso
10 minutes • Admission Ticket Free
6
The Chicago Theatre
15 minutes • Admission Ticket Not Included
7
Macy's on State Street
10 minutes • Admission Ticket Free
8
Chicago Cultural Center
15 minutes • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Wheelchair accessible
- Service animals allowed
- Near public transportation
- Surfaces are wheelchair accessible
- Not recommended for travelers with back problems
- Not recommended for pregnant travelers
- No heart problems or other serious medical conditions
- Travelers should have a moderate physical fitness level
- Please bear in mind that this tour is an adventurous 2-hour, 2-mile, indoor/outdoor, downstairs/upstairs, elevator/escalator experience.
- This tour/activity will have a maximum of 10 travelers
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
5.0
based on 237 reviews
Sort by: Most insightful
Michelle_R, Jul 2026
Collin was very knowledgeable and a lot of fun. We were in a small group of people for the tour. It felt like we were all friends by the end. We loved learning about Chicago.
Bob_R, Jul 2026
First, Colin is an excellent tour guide. His knowledge of the city and its unique history. He is very extensive. I would give him an A+ or a higher grade if I could. I like the fact he used lies his iPad to enhance his presentations. He was very accommodating to our questions needs and interest. I have taken this tour before with someone else and I learned so much more on his tour.
Elise_D, Jul 2026
Loved the history, delivered with humor and full of interesting details. Colin is an expert on Chicago history! So fun to get into places that we’ve walked by for years to reveal treasures of the city. A must-do tour!
David_B, Jul 2026
Colin was an excellent tour guide. He took us to great examples of architecture and filled us in on some of the history of the city. 2 1/2 hours flew by, and was a pleasant tour, even in the heat!
Kristin_E, May 2026
Colin is really knowledgeable about the city and showed us some incredible buildings and lobbies. While the architectural boat tour is great - getting a close look with Colin was amazing. We never would have known the true history and the beauty of the various places he shared with us. I would love to go back and take my family on his tour. Thanks Colin!
Jacquelyn_F, May 2026
Colin's varied experiences in life, and his enthusiasm about Chicago, make for a very enjoyable tour of the city. He took us to many interesting buildings and shared their history. We were a small group of four on his tour so we could hear well and ask a lot of questions. I would certainly recommend it to anyone.
Christy_L, Apr 2026
I highly recommend this tour! Colin brings you into some amazing buildings that you would have just walked on by not knowing what you’re missing. I even went back later in the day to show my husband some of my favorite spots since he was unable to go on the tour.
Julie_B, Apr 2026
Colin was a great tour guide. He clearly knew his history. The tour was amazing. I was able to tour the sites of Chicago supported with the immense local knowledge from Colin.
Lynn_H, Apr 2026
Colin was an outstanding guide who brought Chicago's history alive in a very unique way. He used an iPad throughout the tour to show us historical images and visualizations of the exact locations we were visiting. We had plenty of opportunities to ask Colin questions, and he was always ready with thoughtful and detailed answers. It was an engaging, memorable tour that combined storytelling, visuals, and genuine passion for Chicago's history. We couldn't recommend it highly enough.
HyeSeung_B, Mar 2026
Colin was very knowledgeable about Chicago history! He was friendly and easy going! Loved the tour!!
CRAIG_B, Mar 2026
He knows what went on and what is going on. Great walk! He points out something almost every block. He even has ideas for you to do after the tour for your whole stay in Chicago.
Shawna_L, Feb 2026
Lots of walking, beautiful sights, and history. Bring a fully charged phone/camera. Colin is really nice, thoughtful in knowing where the good restrooms are!
Connie_M, Nov 2025
Nice to be able to see steller building Tiffany glass domes and much more, Collin if fun is giving out the history stories.
Amy_F, Nov 2025
We have done several tours in Chicago over the years, including one that was architectural-specific. Collin was by far the most knowledgeable. He took us to several hidden gems that other tours didn't even hint at. On top of his witticism, we are still discussing some of the historical stories he shared. Best time investment of our visit! Now we just need Collin to do a Chicago foodie tour.
Susan_G, Sep 2025
Colin is very knowledgeable and provided so much cool information about Chicago, its sites, and its history
Karin_D, Sep 2025
We really loved this walking tour! Colin is really informative, enjoyable and you can tell he has a passion for the content. Loved the supporting pictures and footage he shared.
Natalie_B, Sep 2025
Colin took us to beautiful architectural sites that even long time Chicagoans likely never admire. He was informative, articulate and moved at a good pace for our group of 8. I highly recommend this tour to even the most seasoned Chicago residents!!
Jamil_M, Sep 2025
The walk was easy. Great and knowledgeable tour guide (Collin). Gave good reception for what else to see not on the tour. Throughly enjoyed this tour.
Gloria_F, Sep 2025
Great tour. Fun facts & real history. Colin was just right, beautiful architecture & historical information….Daisy didn’t do it. 😂
Amanda_S, Aug 2025
The tour was a lot of fun, and I feel like we learned a lot. He is very knowledgeable about the city
Karen_M, Aug 2025
We enjoyed a fun tour with very knowledgeable guide. Lots of interesting history and beautiful architecture!
Hinda_D, Aug 2025
We were the only ones on our very hot, but super fun and interesting tour of downtown Chicago. It was an excellent, informative tour with lots of tidbits of history and photos that made everything memorable.
Melissa_L, Aug 2025
It was an exceptional tour, he made it funny, enjoyable, and very informative with abundant facts. It was the best tour by far during our visit to Chicago. I would higher recommend this tour.
Yasmina_A, Jul 2025
Amazing experience ! Collin was super friendly and the explanations were great. Would highly recommend ! Thank again !!
Kathleen_T, Jul 2025
This was a fantastic tour! Colin was very knowledgeable and upbeat! He kept us interested for the entire tour. It was a great variety of stops. I learned lots that I never knew about Chicago and have lived here 68 years! Take this tour!!!
Gary_G, Jul 2025
Colin was extremely knowledgeable about the history and architecture of Chicago. The tour was interesting, entertaining, and highly enjoyable. He puts a tremendous amount of effort into preparation with added electronic images to supplement the discussion. Lots of hidden gems that are well worth seeing and photographing. The walking pace was not strenuous and time is allowed for a brief break if needed. Just bring an umbrella if it’s raining, and you will still have a great time. I highly recommend this tour.
Larry_S, Jul 2025
Colin was an interesting and knowledgeable tour guide. He shared details about Chicago history and walked us through historic buildings and amazing architecture. You will enjoy joining him for a tour
Karen_V, Jul 2025
Colin is very personable and knowledgeable, even though he’s relatively young. He’s interested in art and will show you a bunch of cool things in the city. He’s also very adaptable when we started getting rained on and he just pivoted to underground walkways.
Michael_M, Jul 2025
Walking with Colin is part history, part comedy, part mystery and totally unforgettable. It's super interactive, and Colin's storytelling is so vivid the stories really stick with you. You'll laugh, learn, and see the city in a whole new way. I’d absolutely recommend this tour to anyone visiting Chicago!
sandra_e, Jul 2025
Colin was a good guide as far as showing us interesting buildings on our walk but not as attentive as he could have been. He crossed the street several times before all of us were at the cross walk, leaving those of us who were taking photographs or who were slower walkers behind.
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