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Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking tour reveals the secrets of the city’s skyline and its shadowy history. Now with 2 Christmas related stops, and the tour ending right by the Christkindlmarket. Led by a passionate local guide, you’ll visit architectural gems and hidden landmarks that boat tours miss bringing Chicago’s rich and eerie past to life.
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
All areas and surfaces are wheelchair accessible
Suitable for all physical fitness levels
For a full refund, cancel at least 24 hours before the scheduled departure time.
Local guide
Gratuity
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.
320 reviews
Total reviews and rating from Viator & Tripadvisor
Margaret S,
Nov 25, 2025
- Review from Viator
My husband and I had a great time on this tour. Our guide David was very knowledgeable and passionate. The buildings were spectacular and the true crime stories were wild.







sailorwc,
Nov 25, 2025
- Review from Tripadvisor
Great tour and loved seeing the inside of several historic buildings. Great info and fun stories! Definitely would recommend!
285melindan,
Nov 24, 2025
- Review from Tripadvisor
The tour was interesting and informative. David did a great job. It was a small group. Good blend of architecture and historical crime.
Connector05274549595,
Nov 24, 2025
- Review from Tripadvisor
Awesome! David was very enthusiastic and told GREAT stories. He was also great at communicating ahead of time on where to meet him and how the tour would work. Highly recommend!
Jen S,
Nov 24, 2025
- Review from Viator
There is quite a bit of walking, partly indoors partly outdoors. Very enthusiastic and knowledgeable guide.
Stefanie H,
Nov 24, 2025
- Review from Viator
Great tour with a perfect combination of architecture and crime. David was a great guide and answered all our questions and more!
Genevieve G,
Nov 23, 2025
- Review from Viator
Joseph is obviously super passionate about this tour. Loved his extra timid bits in between the spiels. Will definitely be recommending this tour to people in the future.
J6348JLcourtneyk,
Nov 22, 2025
- Review from Tripadvisor
David was an enthusiastic and knowledgeable guide. I know he is studying to be a teacher and it clearly showed that this is his calling.
Excursion14862543487,
Nov 21, 2025
- Review from Tripadvisor
The tour was fun, well paced, and very informative. David’s knowledge and enthusiasm for each location kept us engaged and demonstrated how much he cares about what he does. I’d highly recommend this tour to anyone visiting Chicago. We really enjoyed it!

jfab31,
Nov 17, 2025
- Review from Tripadvisor
Great experience!! Since it was a solo tour I was able to ask questions and learn even more about the Chicago Loop area :))
Operated by Local Chicago Tours