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Beyond Chicago

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Recommended by 100% of travelers
Badge of Excellence
Chicago, USA
Popular pick
Booked 5+ times last week!
  • 2 hours (approx.)
  • Mobile ticket
  • Offered in: English

Why travelers loved this

5.0
·
· Wesley_S ·
Jul 2026
Great tour! Colin is very charismatic and engaging, very knowledgeable of the city, we learned a lot of little interesting details that would otherwise be skipped on a large group tours. This was a small group and felt almost personalized. Definitely recommend.
· Maria_G ·
Jul 2026
Great start to our trip! Colin was very knowledgeable and resourceful. Helped us to learn about the city’s history and insightful on what’s happening today. Love that he offered suggestions on things we could do, etc. Thank you!

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 Center
      78 E Washington St, Chicago, IL 60602, USA

      We will conclude our tour at the magnificent "People's Palace", The Chicago Cultural Center.

    Itinerary

    1

    Palmer House Hilton Historic Lobby

    15 minutesAdmission Ticket Free

    2

    Marquette Building

    10 minutesAdmission Ticket Free

    3

    Calder’s Flamingo

    10 minutesAdmission Ticket Free

    4

    The Rookery Building

    15 minutesAdmission Ticket Free

    5

    The Picasso

    10 minutesAdmission Ticket Free

    6

    The Chicago Theatre

    15 minutesAdmission Ticket Not Included

    7

    Macy's on State Street

    10 minutesAdmission Ticket Free

    8

    Chicago Cultural Center

    15 minutesAdmission 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

    Cancellation Policy

    You can cancel up to 24 hours in advance of the experience for a full refund.

    Traveler Photos

    Gallery picture 1 (from a traveler's review)
    Gallery picture 2 (from a traveler's review)
    Gallery picture 3 (from a traveler's review)
    Gallery picture 4 (from a traveler's review)
    Gallery picture 5 (from a traveler's review)

    Reviews

    5.0
    based on 245 reviews
    Total reviews and rating from Viator & Tripadvisor
    Sort by: Most insightful

    Very informative and engaging!

    Brittany_W, Sep 2026
    Colin's tour was very informative and engaging, covering a good range of topics (history, architecture, art, etc.). I estimate our total walking distance was somewhere around 1.5 miles, and it took about 2 hours. I would definitely recommend this tour to future travelers. It also ends in a convenient location for continued exploration (Cultural Center / Millennium Park).

    Must Do! Colin is Fantastic.

    Wesley_S, Jul 2026
    Great tour! Colin is very charismatic and engaging, very knowledgeable of the city, we learned a lot of little interesting details that would otherwise be skipped on a large group tours. This was a small group and felt almost personalized. Definitely recommend.

    Great start to the trip!

    Maria_G, Jul 2026
    Great start to our trip! Colin was very knowledgeable and resourceful. Helped us to learn about the city’s history and insightful on what’s happening today. Love that he offered suggestions on things we could do, etc. Thank you!

    Colin is great! A must while in Chicago.

    Elizabeth_A, Jul 2026
    Fun and engaging tour of Chicago. His pace is perfect and his voice is clear and loud enough to hear without being obnoxious. Good stories and interesting facts. Get it done!!!

    Chicago tour.

    Sade_S, Jul 2026
    Omg we loved loved loved Colin. He was the best tour guide ever. If you're in need of a tour please consider him.🥰

    Amazing tour!

    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.

    Chicago’s skyscrapers interior hidden treasures

    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.

    Highly recommended!

    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!

    Walking Tour with Colin

    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!

    Colin is really...

    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!

    Colin's varied...

    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.

    Fantastic tour!

    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.

    Excellent. Must do.

    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.

    Colin's Fabulous Historical Tour

    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.

    Chicago walking tour

    HyeSeung_B, Mar 2026
    Colin was very knowledgeable about Chicago history! He was friendly and easy going! Loved the tour!!

    He knows what went on and...

    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.

    Wear your walking shoes

    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!

    steller

    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.

    Even Stevie Wonder Would Give 5 Stars

    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.

    Colin is very...

    Susan_G, Sep 2025
    Colin is very knowledgeable and provided so much cool information about Chicago, its sites, and its history

    Fantastic tour - take this!

    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.

    Outstanding

    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!!

    The walk was easy. Great...

    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.

    Chicago 101

    Gloria_F, Sep 2025
    Great tour. Fun facts & real history. Colin was just right, beautiful architecture & historical information….Daisy didn’t do it. 😂

    The tour was a lot of...

    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

    Chicago Walking Tour

    Karen_M, Aug 2025
    We enjoyed a fun tour with very knowledgeable guide. Lots of interesting history and beautiful architecture!

    A very worthwhile tour.

    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.

    Exceptional Tour

    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.

    Amazing experience

    Yasmina_A, Jul 2025
    Amazing experience ! Collin was super friendly and the explanations were great. Would highly recommend ! Thank again !!

    Excellent Tour!

    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!!!

    From $44.00

    per person

    up to 24 hours before the experience starts (local time)

    Book ahead!
    On average, this is booked 19 days in advance.

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