Embark on a history-based guided walking tour and discover the stories of Chicago’s gangsters and ghosts. Learn about the city’s darker side and creepy past as you explore the Chicago Loop district.
About this activity
- Free cancellation
- Cancel up to 24 hours in advance for a full refund
- Reserve now & pay later
- Keep your travel plans flexible — book your spot and pay nothing today.
- Duration 2 hours
- Check availability to see starting times.
- Live tour guide
- English
- Wheelchair accessible
Experience
Itinerary
Starting location:
Chicago Gangsters and Ghosts Tours
Chicago Riverwalk
The Chicago Theatre
Palmer House A Hilton
Cloud Gate
Art Institute of Chicago
The Congress Plaza Hotel & Convention Center
Finish at:
The Congress Plaza Hotel & Convention Center
Main stop
For reference only. Itineraries are subject to change.
Highlights
- Learn about the dark history of Chicago's South Loop from a historian guide
- Hear true tales of Chicago's gangster past and learn how Al Capone ran his empire
- Listen to eerie tales of ghosts that are said to lurk around historic landmarks
- Explore Death Alley, Chicago Riverwalk, the Palmer House and the Chicago Theatre
- Visit the Congress Hotel and learn about the creepy incidents on the 12th floor
Full description
Discover a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn.
Meet your guide in the heart of the Chicago South Loop, known as a notorious vice district during the 1920s and 30s. Stroll through his now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers.
Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". You will also enjoy a short rest stop at a famous former gangster hangout.
Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing with a visit to the Congress Hotel, one of the most haunted places in Illinois.
Includes
- Guided walking tour
- Historian guide
- Visits inside the Congress Hotel and the Palmer House
- Tips (optional)
Not suitable for
- People with mobility impairments
Select participants and date
Participants
Date
Meeting point
Meet your guide outside the Wyndham Hotel building in front of the large "Hoyt's" restaurant sign.
Open in Google Maps ⟶Important information
What to bring
- Comfortable shoes
- Water
- Comfortable clothes
Not allowed
- Luggage or large bags
Know before you go
- This tour is not recommended for people with infants
- The tour is 1.5 miles total walking, with a 20-minute break at a famous gangster hangout
- Children aged 6 and under can join this tour for free