Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
Active
2h
For a full refund, cancel at least 24 hours before the scheduled departure time.
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Mobile or paper ticket accepted
About this experience
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.
Available options
Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
What's included
Expert guide
Detailed itinerary
1
We will surprise you with our itinerary -- half in River North, half in Chicago's Loop neighborhood. We will visit various dark sites in both neighborhoods, including the hotel where a psychopathic serial killer stayed after committing his crimes, and a gangster hangout with a hidden vault.
2
We are purposely giving a vague description of where we'll be so that you'll be surprised at every turn with the tales of ghosts, gangsters, disasters, and more! From cold spots, to dead energy, to stories of the macabre, this tour will show you the darker side of Chicago.
What's not included
Gratuities
Available languages
Guide guide
EN
Reviews breakdown
Viator
4.6
5 reviews
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1
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Tripadvisor
5.0
21 reviews
5★
21
4★
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Important information
Not recommended for travelers with spinal injuries
Service animals allowed
Public transportation options are available nearby
Infants and small children can ride in a pram or stroller
Travelers should have at least a moderate level of physical fitness
Meeting point
We meet directly in front of the Fedex store, near the corner of Erie & Dearborn. Please check in with your guide upon arrival!
About Chicago
Chicago is a vibrant city known for its stunning architecture, rich cultural heritage, and world-class cuisine. Situated along the shores of Lake Michigan, it offers a unique blend of urban excitement and natural beauty, making it a must-visit destination for travelers from around the globe.
Top Attractions
Millennium Park
Millennium Park is a famous public park in downtown Chicago, known for its modern art and architecture. It's home to the iconic Cloud Gate sculpture, also known as 'The Bean'.
Park
1-2 hours
Free
Art Institute of Chicago
One of the oldest and largest art museums in the United States, the Art Institute of Chicago houses an impressive collection of artworks from around the world.
Museum
2-3 hours
$25 (adults), Free for children under 14
Skydeck Chicago
Located on the 103rd floor of the Willis Tower, Skydeck Chicago offers breathtaking views of the city and Lake Michigan. Visitors can step out onto The Ledge, a glass balcony extending out from the building.
Observation Deck
1-2 hours
$28 (adults), $20 (children 3-11)
Navy Pier
Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.
Entertainment
2-4 hours
Free to enter, individual attractions have varying costs
Wrigley Field
Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.
Sports
2-4 hours (game duration varies)
Ticket prices vary depending on the game and seating
Must-Try Local Dishes
Deep-Dish Pizza
A thick, buttery crust filled with layers of cheese, toppings, and tomato sauce. It's a Chicago classic and a must-try for pizza lovers.
Dinner
Contains gluten and dairy. Vegetarian and vegan options are available at some restaurants.
Chicago-Style Hot Dog
A steamed or grilled all-beef hot dog topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato wedges, pickled sport peppers, and a dash of celery salt, all served on a poppy seed bun.
Snack
Contains gluten and dairy. Vegetarian and vegan options are available at some hot dog stands.
Italian Beef Sandwich
Thinly sliced beef cooked in its own juices and served on an Italian roll. It's typically dipped in the juices and topped with sweet or hot peppers.
Lunch/Dinner
Contains gluten and beef. Vegetarian and vegan options are available at some Italian beef restaurants.
Chicago-Style Popcorn
A sweet and savory snack made with caramel and cheese-flavored popcorn, often sold in colorful boxes at street corners and ballgames.
Snack
Contains dairy. Vegetarian and vegan options are available at some popcorn stands.
Popular Activities
Kayaking on the Chicago River
Biking along Lake Michigan
Rock climbing at First Ascent
Picnicking in Millennium Park
Yoga in the park
Spa treatments at The Peninsula Chicago
Visiting the Art Institute of Chicago
Attending a performance at the Chicago Symphony Orchestra
Best Time to Visit
May to September
This is the best time to visit Chicago for outdoor activities, festivals, and sightseeing. The weather is warm and pleasant, making it ideal for exploring the city's parks and attractions.
15°C to 30°C
59°F to 86°F
Practical Information
Language
- Official: English
- Widely spoken: Spanish, Polish, Chinese
- English: Widely spoken
Currency
United States Dollar (USD)
Time Zone
Central Time Zone (CT) (GMT-6)
Electricity
120VV, 60HzHz
Safety Information
Overall Safety Rating: Generally safe
Chicago is generally safe for tourists, but visitors should be aware of their surroundings and take precautions to protect themselves and their belongings. Some areas of the city have higher crime rates, and visitors should research their destinations before traveling.
Important Precautions:
- • Be aware of your surroundings and keep valuables secure
- • Use licensed taxis or ride-sharing services
- • Avoid walking alone in isolated or poorly lit areas, especially at night
Getting there
By air
- O'Hare International Airport • 27 km (17 miles) from city center
- Midway International Airport • 13 km (8 miles) from city center
By train
Union Station, Ogilvie Transportation Center
By bus
Greyhound Station, Megabus Terminal
Getting around
Public transport
The 'L' is a convenient and affordable way to get around Chicago. It consists of eight color-coded lines.
Taxis
Available • Apps: Uber, Lyft
Rentals
Car, Bike, Scooter
Neighborhoods
The Loop
Lincoln Park
Wicker Park
Magnificent Mile
Pilsen
Day trips
Navy Pier
2 km (1.2 miles) • Half day to full day
Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.
Wrigley Field
10 km (6.2 miles) • Half day to full day
Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.
Museum Campus
3 km (1.9 miles) • Half day to full day
The Museum Campus is a 57-acre park located on the southern tip of Grant Park in Chicago. It's home to several world-class museums, including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.
Festivals
Lollapalooza • Early August (4-day festival)
Chicago Jazz Festival • Late August to early September (weekend festival)
Chicago Food Festival • Early September (weekend festival)
Pro tips
- Visit popular attractions early in the morning or late in the afternoon to avoid crowds and long wait times
- Use the Ventra card for easy and convenient payments on public transportation
- Explore the city's diverse neighborhoods and culinary scene to get a true sense of Chicago's character and culture
- Take an architecture river cruise to see the city's stunning skyline and learn about its architectural history
- Visit the city's many parks and outdoor spaces to enjoy nature and outdoor activities, even in the heart of the city
Get Price
per person
Price varies by option
Secure booking
Free cancellation available
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