Chicago Architecture & Dark History Tour

331 Ratings

Chicago

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Explore Chicago’s skyline and dark past with our expert guide. Discover architectural marvels and infamous crime stories in one thrilling tour.

Duration: 1 hour, 45 minutes

Cancellation: 24 hours

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Highlights

Palmer House Hilton Historic Lobby - Step back in time at the historic Palmer House while uncovering the dark history.
Downtown / The Loop - We’ll also explore other stunning buildings and learn more about Chicagos dark past.
Chase Tower - We’ll conclude the tour at Chase Tower, a building known for its fascinating illusion.

What's Included

Local guide

What's Not Included

Gratuity

Additional Information

Experience the perfect blend of Chicago’s breathtaking architecture and its intriguing history. Inspired by “Devil in the White City,” this expertly guided walking tour unveils the mysteries of the city’s skyline and its darker stories. The Christmas Edition is primarily indoors, featuring two festive stops and concluding near the Christkindlmarket….

Location

118 S Wabash Ave

South Wabash Avenue

We’ll meet under the Palmer House canopy on the Wabash side, right next to Poké Poké.

Cancellation Policy

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

Customer Ratings

5.0

(331 Ratings)

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Nottoosoon

Oct 22, 2025

Great reviews of some of the city's best architectural sites - David provided us with some great insights into Chicago's architectural sites and local crime lore that was very interesting. So nice to have a local expert to share the secrets and less well known facts of the city's iconic buildings.

Review provided by Tripadvisor

Grace5678

Oct 21, 2025

Highly recommend! - Joseph was great! I really enjoyed the tour! Learned some cool new things and some crazy true crime facts!! Highly recommend!

Review provided by Tripadvisor

Erinomiles

Oct 21, 2025

Wonderful walking tour! - Great walking tour exploring architecture and crime. Joseph did a wonderful job explaining the architecture and telling intriguing stories of crime!

Review provided by Tripadvisor

854deannek

Oct 20, 2025

Great walking history tour for Halloween! - David was an excellent tour guide and storyteller. He was able to take us inside several buildings, which was really interesting. When we were walking on the sidewalks, the noise from traffic was loud, but he made sure we could hear him when we gathered. I loved learning the history of Chicago and the infamous people who lived there. And Death Alley!

Review provided by Tripadvisor

Nathan_m

Oct 19, 2025

The guide was great and... - The guide was great and very knowledgeable. The tour was informative and we saw some cool buildings.!

Review provided by Viator

Freedom52877122659

Oct 19, 2025

Fantastic - Super interesting and fun, and I would honestly do it again. It wasn’t too long or too short, and perfect for my family’s time in the city

Review provided by Tripadvisor

Dave_l

Oct 19, 2025

My date and I were fans... - My date and I were fans of Jonas - she described him as likable, charming, and sarcastic in a good way. Tour was fun and learned quite a few things

Review provided by Viator

531anneisabelles

Oct 18, 2025

Fantastic tour! - Thank you Jonah for this amazing tour! We have learned so much and we had so much fun. We will be recommending this tour to anyone who visits!

Review provided by Tripadvisor

P6366jasamantham

Oct 18, 2025

spooky silly architecture crime tour 10/10 - Very informative and interesting! Makes me see Chicago in a new light, definitely recommend to anyone visiting the city !!

Review provided by Tripadvisor

Kymberleeg2025

Oct 18, 2025

Tour - They were very accommodating and helpful and had a lot of information about the tour. They provided a lot of support and guidance. It was very fun and safe

Review provided by Tripadvisor

Check Availability

From $35

up to 15 guests

1 - Adult