Guided tour

Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour

Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour

From US$ 75.60 per person

Thrills, gangsters, murder, and mayhem are all on the agenda on this fun but chilling nighttime Segway tour of Chicago. Guides become ghost hunters as you creep through the shadows to sites such as Haunted Fort Dearborn, Death Alley and so many more.

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
Small group
Limited to 8 participants


  • Visit Chicago's most frightening ghosts at the Congress Hotel, Death Alley,the site of the Eastland Disaster and Fort Dearborn.
  • Hear gruesome tales of Al Capone's yacht and the most fearsome hotel in the city
  • Zip along Michigan Avenue listening to spooky stories
  • Cruise through the loop as you are entertained by professional guides
  • See the skyline illuminated in its evening glory
Full description
If you are looking for fun things to do in Chicago at night, then this haunted Segway tour of the Windy City’s ghoulish murders and gruesome disasters, ghastly gangsters and ghostly tails is just for you. You will glide eerily around the streets escorted by an expert Segway guide. Creep through the shadows to hear true stories of ghosts and view the sites where some of Chicago's most appalling tragedies took place. You will sneak down to Lake Michigan for a look at Al Capone's haunted yacht, and pass by a Michigan Avenue hotel, alleged to be the most haunted in the city. Get the shivers as you hear accounts of the many unexplainable deaths and tales of the self-playing piano. Continue through the dark streets of downtown Chicago to Death Alley, site of the Iroquois Theatre fire where over 600 Chicagoans perished in a single day. Glide along the Chicago River to view the site of the worst maritime disaster in the city’s history, when 800 people perished. Then slope along the River Walk to see the site of the Fort Dearborn Massacre. If you haven’t got the shivers by now, then you must be made of stone. Perhaps you are even one of the walking dead…
  • Helmets
  • Thorough segway orientation by a certified Segway instructor
  • Professional guide
    Not suitable for
    • Children under 12 years
    • Pregnant women
    • People with mobility impairments
    • People over 260 lbs (118 kg)
    • People under 99 lbs (45 kg)
    Covid-19 precautions
    Safety measures in place
    • All areas that customers touch are frequently cleaned
    • The number of visitors is limited to reduce crowds
    Traveler requirements
    • You are required to bring and wear a mask

    Select participants and date



    Prepare for the activity

    Meeting point

    Office is located at the NE corner of Columbus Drive and Monroe Street. When you are on the intersection of Columbus Drive and Monroe look for the orange flag signs that say "Segway Tours." The supplier is located one level below the street and has Orange A-frame signs with arrows pointing the way. Please call 312.552.5100 if you get lost. Please arrive 15 minutes before scheduled tour for check-in. Late arrivals will not be able to join tour.

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    Important information

    Not allowed

    • Sandals or flip flops
    • Pets
    • Luggage or large bags
    • Alcohol and drugs

    Know before you go

    • All participants must sign a waiver and release. You must be over 12 years old to participate, and under-18s must be accompanied by an adult. Participants must weigh a minimum of 100 pounds and less than 260 pounds. Please do not wear shape-up shoes or any shoe without a flat sole. Pregnant women may not participate in this activity. Those suffering from seizure disorders, unable to climb stairs without assistance, with recent joint replacements, or the unable to stand for more than 1 hour should not participate. Further restrictions may apply.
    • The bathrooms near the office are closed for maintenance. Please use the washroom prior to your arrival. There are several bathroom stops along the tour route.
    Customer reviews

    Overall rating

    4 /5

    based on 2 reviews

    Review summary

    • Guide
    • Transportation
    • Value for money

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    Haunted Chicago Segway Tour

    After a brief practice session on the segways (which I needed quite badly it turns out!) we set out after dark on a tour of Chicago's demons! Dan was great fun and stuffed full of info! Obviously being on segways it isn't the most chilling of ghost tours but never the less a hoot! Reccommended

    March 21, 2013

    Not scary but really fun!

    Not scary but fun with loads of interesting stories and anecdotes. Very good value for a segway tour and frankly a relief to be rolling around in the evening after a day of trecking through the streets in the sweltering heat! Paul was an exemplary guide -- entertaining, helpful, informative, and full of tips to do around town for the duration of your stay.

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    July 11, 2013

    Chicago ghost tour

    Very enjoyable right from the beginning with the hilarious instructional video! The guide was great and the other guys in our tour group were nice too, we even hung out with some of them afterwards. Very nice way to see Chicago after dark and hear some funny ghost stories instead of the normal sight-seeing. Probably best for people who are in town for a week or so rather than just a couple of days.

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    August 31, 2013

    Great option for touring the city with teenagers

    The views of the city at night were fantastic! It’s a great way to tour the city with teenagers. There’s not a lot that interests them when it comes to hanging out with parents but this is a win!

    October 12, 2019

    Jay told great stories and led us around the beautiful city of Chicago

    October 21, 2019

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    Product ID: 16045