




Available languages
1 hour 30 minutes
Mobile ticket
Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past. Visit Prohibition Era speakeasy bars, sites of real life mob shootouts, and haunted tragedies that shape the city's legacy.
This walking tour blends ghost stories, true crime history, and architectural landmarks to reveal the beauty and horror from one of America's most famous time periods, right where it happened.
You'll gain special access to architectural interiors tied to famous history, as you are led by a trained historian tour guide through these famous sites. Learn where Chicago's history still whispers after dark!
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
This is a walking tour, 1.0 Miles over 1.5 Hours
Not recommended for travelers with a cold
Chicago River
Our expert host will meet you at the starting point and begin to explain the architecture and haunted history along the Chicago River.
River North
You will see historic buildings that operated as speakeasy bars of the Prohibition Era, and see famous spots connected to legendary bank robber John Dillinger.
Expert Tour Guide
Go Inside Famous Hotels
Tips and Gratuities for Tour Guide
For a full refund, cancel at least 24 hours before the scheduled departure time.
239 reviews
Total reviews and rating from Viator & Tripadvisor
F8022LPmichellew,Jun 13, 2026
- Review from Tripadvisor
Our guide Braeden was great. Interesting facts and friendly guide. We enjoyed our tour very much.
Global25577869434,Jun 13, 2026
- Review from Tripadvisor
Brayden was an amazing tour guide, who ended up giving our small family group a private tour all over Chicago. He was extremely knowledgeable and personable, even letting us walk in to taste the first ever brownie! I would recommend this tour for anyone who has not been to Chicago before. Also involves a good amount of walking, and sprinkles in more than just crime and gangster discussion, including some talks about the Chicago fire and little known maritime accident. Great time!
Micah W,Jun 13, 2026
- Review from Tripadvisor
Andre is the most phenomenal tour guide we’ve had. He brings the back of an alley wall to life with an engaging story that draws you in. Highly recommended. Don’t hesitate to book it.
W8570LZjoshuas,Jun 13, 2026
- Review from Tripadvisor
Really fun tour and Andre's knowledge of chicago history was impressive. His delivery and theatre background made it even more fun. Highly recommend for a memorable slice of Chicago history.
145artv,Jun 13, 2026
- Review from Tripadvisor
Very charismatic and answered all questions
Sherpa569755,Jun 13, 2026
- Review from Tripadvisor
Andre was super knowledgeable, passionate, and guided us well. Shared the history of much of the city. Sort of a movie format too since he shared many stories as well.
Happiness718043,Jun 13, 2026
- Review from Tripadvisor
Super entertaining and educational. Andre is a great storyteller. If you like true crimes, you’ll love this tour.

sgoldman87,Jun 13, 2026
- Review from Tripadvisor
Andre has wealth of knowledge and is super animated and enthusiastic! I was fully engaged the whole time, wanting to learn more!
ggopman,Jun 13, 2026
- Review from Tripadvisor
It’s fun and charming. He’s very knowlegable.

brandongoldman,Jun 13, 2026
- Review from Tripadvisor
Andre is the best tour guide ever. He led an incredible tour for my 40th birthday with more than a dozen of my friends. Andre is the man! Take his tour

Operated by Magnifico Tours