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Explore more things to do in Chicago

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Chicago: Gangsters and Ghosts Guided Walking Tour

Top rated
4.7181115 out of 5 stars
4.7
4.7181115 out of 5 stars
1419 reviews
allyalmorephoto@allyalmorephoto
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Chicago: Gangsters and Ghosts Guided Walking Tour
Top rated
4.7181115 out of 5 stars
4.7
4.7181115 out of 5 stars
1419 reviews

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 tour

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

Highlighted reviews from other travelers

S
Samer – Germany

Allain was amazing . Very informative and funny. The tour wouldn’t have been the same without him :)

I
Ian – United Kingdom

Great fun tour from an entertaining guide, Adam gave us some interesting background on the city mixed with tales of its darker side.

Select participants and date

Participants

Itinerary

  • Timeline stop icon

    Starting location:

    Chicago Gangsters and Ghosts Tours

  • Timeline stop icon

    Chicago Riverwalk

  • Timeline stop icon

    The Chicago Theatre

  • Timeline stop icon

    Palmer House A Hilton

  • Timeline stop icon

    Cloud Gate

  • Timeline stop icon

    Art Institute of Chicago

  • Timeline stop icon

    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, either on foot or by bus. 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 and kick off your guided walk through Chicago's notorious South Loop, known as a 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

Meeting point

Please meet your guide outside "Hoyt's Tavern", which is adjacent to the Royal Sonesta hotel.

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

From $36 per person

Reserve now & pay later to book your spot and pay nothing today
Reserve now & pay later to book your spot and pay nothing today

Customer reviews

Overall rating

4.7 /5

based on 1419 reviews

Review summary

  • Guide
    4.8/5
  • Value for money
    4.6/5

Customer photos

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S
Samer – GermanyJune 6, 2025 – Verified booking
Allain was amazing . Very informative and funny. The tour wouldn’t have been the same without him :)
I
Ian – United KingdomJune 5, 2025 – Verified booking
Great fun tour from an entertaining guide, Adam gave us some interesting background on the city mixed with tales of its darker side.
C
Chantelle – CanadaJune 1, 2025 – Verified booking
Max was our tour guide! He gave great descriptions of the haunted past of Chicago. We learned lots about Chicago's history and how the influence of the gangsters shaped the city into what it is today. Max’s storytelling was engaging and full of personality—he really brought the stories to life. Highly recommend this tour for anyone looking to explore a darker, fascinating side of Chicago's past!

Product ID: 234682

Activity provider:Chicago Gangsters and Ghosts Tours
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