Guided tour

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

From $27 per person

Explore Chicago from the perspective of ghosts and gangsters. Take a 2-hour 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
Covid-19 precautions
Special health and safety measures apply. Learn more
Mobile ticketing
Use your phone or print your voucher
Duration 2 hours
Check availability to see starting times.
Instant confirmation
Live tour guide
Wheelchair accessible


  • 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
Take a 2-hour guided walking tour through the Chicago Loop and discover the stories of gangsters and ghosts from the city’s past. The Loop was known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone use to party, make deals, and carry out threats. Visit haunted locations and old crime scenes on a tour led by historians. Spooky tales of the ghosts and gangsters of Chicago’s street will be shared along the way. Stop at the Congress Hotel, Death Alley, and the Palmer House. This is a family-friendly tour. with frequent stops and a refreshment and restroom break.
  • 2-hour tour
  • Guide
  • Visits inside the Congress Hotel and the Palmer House
    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



    Prepare for the activity

    Meeting point

    The tour meets outside of the Wyndham Hotel building in front of the large "Hoyt's" restaurant sign.

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    Important information

    What to bring

    • Comfortable shoes

    Not allowed

    • Luggage or large bags

    Know before you go

    • This tour is not recommended for people with limited mobility or with infants
    • Walking shoes are recommended
    • 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 298 reviews

    Review summary

    • Guide
    • Value for money
    • Service
    • Organization

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    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!

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    July 17, 2021

    Conor was our tour guide, my husband and I have an entertainment time with him. We learned interesting and historical stories from Chicago. He was friendly and made the stories interesting. After the tour I was reading all about of some of people he mentioned on his stories. It was sensational standing and seen places where part of the Chicago history occurred. I wished to heard more frightful and scary stories like one he talk to us. Thank you for your guide Conor.

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    May 19, 2021

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    Product ID: 234682