Guided tour

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

From US$ 35 per person

Explore Chicago from the perspective of ghosts and gangsters. Take a history-based guided tour and discover Chicago’s gangsters and ghost stories. See the city’s darker side as you walk through the famous Chicago Loop district.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details. Learn more
Duration 2 hours
Check availability to see starting times.
Live tour guide
Wheelchair accessible


2 hours
  • Chicago Riverwalk

  • The Chicago Theatre

  • Palmer House A Hilton

  • Cloud Gate

  • Art Institute of Chicago

  • The Congress Plaza Hotel & Convention Center

Main stop
End point
  • Acquaint yourself with the dark history of Chicago
  • Enjoy amazing views from Chicago's most famous sightseeing districts
  • Visit notable ghost and gangster locations including the Palmer House
  • Learn how Al Capone ran his empire
Full description

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn.

Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business.

Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

  • Palmer House A Hilton entry ticket
  • The Congress Plaza Hotel & Convention Center entry ticket
  • Access to Chicago Riverwalk
  • Access to Art Institute of Chicago
  • Live tour guide
    Not suitable for
    • People with mobility impairments
    Covid-19 precautions

    You must book this activity online because the ticket office is closed

    Safety measures in place
    • The number of visitors is limited to reduce crowds

    Select participants and date



    Meeting point

    The tour meets outside of 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
    Customer reviews

    Overall rating

    4.7 /5

    based on 455 reviews

    Review summary

    • Guide
    • Value for money
    • Service
    • Organization

    Sort by:

    Traveler type:

    Star rating:

    Nice trip filled with histories of mistery and crime. Our guide Conor was super knowlegable and was able to host us in professional and attractive way. The guide was super passionate about telling is insights and interesting facts about Chicago of the earla 1900’s. Highly recommended if you want to get some knowledge and have some fun.

    Read more

    August 31, 2022

    This was one of the best experience I’ve had in the city! The stories and history Connor told on this tour gave me a deeper love for the marvels of the city! It was like learning the behind the scenes of what Chicago was really like from a gangster point of view. 10/10 would do again.

    July 24, 2021

    Myself, husband and 2 teenage children attended this tour. We all had a lot of fun. Our tour guide Kai did an excellent job of telling us the important and interesting facts about Chicago that we were unfamiliar with. We enjoyed hearing the spooky and chilling events of Chicago's past. We loved hearing about the rival gangs of Chicago during the time of prohibition. Some of the unknown tragedies of Chicago are truly surprising that they have not been talked about more. We definitely recommend this tour!

    Read more

    July 17, 2021

    Product ID: 234682