Haunted Mysteries of Chicago Mob Tour
Fight and fright in the Windy City
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Local experts
Personal stories and insider travel tips -
Top-rated
Thousands of reviews averaging 4.9 stars -
Worry-free booking
Flexible scheduling and refunds
$34
€30
£26
C$48
A$52
-
Local experts
Personal stories and insider travel tips -
Top-rated
Thousands of reviews averaging 4.9 stars -
Worry-free booking
Flexible scheduling and refunds
Highlights
- Visit the favorite hangouts of Chicago’s most infamous gangsters.
- Walk the streets and alleyways that once hummed with illicit activity.
- Hear the ghostly story of the hitchhiking flapper girl who roams the roads as you walk by the start of the legendary Route 66.
- Feel the echoes of departed souls as you stand atop of the remains of the Great Chicago Fire.
- Learn how mobsters used Lake Michigan as their dumping grounds — and for what.
What you'll do
As the sun sets on Chicago’s Magnificent Mile, you’ll walk with the spirits of gangsters and condemned ghosts through the alleys, waterways, backstreets, and famous landmarks of the city.
If you love history, true crime, and spooky ...
As the sun sets on Chicago’s Magnificent Mile, you’ll walk with the spirits of gangsters and condemned ghosts through the alleys, waterways, backstreets, and famous landmarks of the city.
If you love history, true crime, and spooky mysteries, this is the tour for you! On this haunted Chicago walking tour, you’ll hear harrowing tales of how mobsters once ruled the city, ghost stories about historical events and figures, and much more.
Each tour is led by an expert guide with a passion for this city’s unique legacy. Whether you’re visiting Chicago for the first time or have lived here your whole life, this tour’s spine-tingling tales offer exhilarating thrills and chills. Join us as we uncover some of Chicago’s darkest secrets.
Chicago mobsters tour itinerary
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Congress Plaza Hotel
Considered the most haunted hotel in America
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Exchequer Restaurant AKA the 226 Club
Al Capone’s favorite hangout
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Under the “L”
Once a hotbed of crime and vice
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Alley of Death
Known for strange and supernatural activity
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Chicago River
A scenic waterway of age-old tragedy
Plan your trip
Tour ending point
This tour ends near N. Michigan Avenue and Wacker Drive.
Refund policy
We offer a 100% refund up to 24 hours before the start time.
Chicago mobsters tour reviews
Meeting point
Meeting Point
The Congress Plaza Hotel & Convention Center, South Michigan Avenue, Chicago, IL, USA
Meet your tour guide in front of the Congress Plaza Hotel & Convention Center. The hotel address is 520 S. Michigan Ave, Chicago, IL 60605.
FAQs
How much walking is there?
This tour covers about 1.5 miles at a leisurely pace.
What is the cancellation policy?
We understand plans change. We offer a 100% refund or the option to reschedule up to 24 hours before your tour start time. Cancellations within 24 hours aren’t eligible for refunds or rescheduling.
When should I get there?
Plan to show up 15 minutes early. The tour starts promptly, and you may not be able to catch up if you arrive late.
What if it rains?
Our tours run rain or shine. If there’s extreme weather and we have to cancel, you’ll get a full refund.
Are gratuities included?
Tips aren’t included but are always appreciated by our guides. If you think your guide did an outstanding job, a tip is a great way to show that.
