Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
Overview
Discover Chicago’s dark side on a chilling 2-hour walking tour. Strolling just under 2 miles at an easy pace, we reveal stories of gangsters, tragedies, and restless spirits hidden behind the city’s glamorous façade. Hear of hidden mob headquarters, psychopaths in plain sight, and disasters like the Iroquois Fire and Eastland Disaster.
Join us in exploring historic interiors where gangsters once gathered and ghosts are said to linger. Along the way, explore the roots of ghost lore—are they real sightings or tricks of architecture? Decide for yourself if Chicago’s most haunted tales are fact or fiction. Perfect for fall nights and curious minds, this tour blends true crime, gangster history, and ghost stories into an unforgettable experience.
What's Included
- Expert guide
- Gratuities
Meeting Location
34 West Erie Street
Chicago, IL 60654, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
520 South Michigan Avenue
Chicago, IL 60605, USA
This tour ends near (or inside) the most haunted hotel in the country!
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
River North
1 hour Admission Ticket Free
Chicago
1 hour Admission Ticket Free
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Not recommended for travelers with spinal injuries
- Travelers should have at least a moderate level of physical fitness
- Infants and small children can ride in a pram or stroller
- This tour/activity will have a maximum of 20 travelers
Frequently Asked Questions (8)
Q: What is the cancellation policy for the Chicago’s Dark Side: Ghosts, Gangsters, and True Crime Tour?
Cancellation Policy
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Activity code: C-30994P17
Traveler Photos
Reviews
Average 4.89 out of 5 stars based on 81 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (8)
The answers provided below were previously given in response to questions from City Sky Diving customers.
Filter by:
- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (CST).
- Expert guide.
- Gratuities.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025The minimum age to participate is 5. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour is as follows:
- Service animals allowed
- Public transportation options are available nearby
- Not recommended for travelers with spinal injuries
- Travelers should have at least a moderate level of physical fitness
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Chicago’s Dark Side: Ghosts, Gangsters, and True Crime Tour will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- Expert guide
- Gratuities
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Not recommended for travelers with spinal injuries
- Travelers should have at least a moderate level of physical fitness
- Infants and small children can ride in a pram or stroller
- This tour/activity will have a maximum of 20 travelers
