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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. The Christmas Version is almost all INDOOR, 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.
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.
Local guide
Gratuity
330 reviews
Total reviews and rating from Viator & Tripadvisor
Kaitlyn K,,Dec 13, 2025
- Review from Viator
Great tour! Joseph was very informative and gave a great tour hitting all the highlights. Also stops inside a lot which is nice for the cold days. Would definitely recommend!
Lauren S,,Dec 13, 2025
- Review from Viator
This tour was fascinating and Joseph was such an engaging tour guide! A majority of the tour was spent inside looking at interior architecture, with brief walks outside to get to the next destination (much appreciated on this 10 degree winter day!) Would definitely book again
Lucy W,,Dec 7, 2025
- Review from Viator
I was a little worried to do this in the winter, but it was a wonderful balance of time spent indoors and outdoors. Kris was so knowledgeable and engaging and we both had a great time!
NorthStar700512,,Nov 30, 2025
- Review from Tripadvisor
This was a unique experience, as this was our first time in Chicago. The time allotted for our small group to learn about architecture and crime was fabulously tied together. It was so much fun and interesting to learn about facts that change the history of Chicago. I would take this tour again nd highly recommend it to visitors.
omansha2025,,Nov 30, 2025
- Review from Tripadvisor
It was a great experience with David. Thanks alot, he was very knowledgeable and fun to talk to. Would definitely recommend this.
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.
Operated by Local Chicago Tours