Haunted Chicago Segway Tour: Ghosts & Gangsters
Roll through Chicago's dark past: haunted theaters, mob assassinations, and the Outfit's secret tunnels
A 2-hour Segway tour through Chicago's haunted and criminal history, where you glide past the Iroquois Theater Fire, Marshall Field's, and mob-run speakeasies while a certified guide recounts ghost stories and tales of Al Capone's reign. The tour includes helmet, Segway orientation, and a guide in English; groups stay under six riders, and you need to arrive 15 minutes early for training and waivers.
2h
Step-by-step itinerary
Segway tour of haunted Chicago sites
- Arrive 15 minutes early to check in
- Fill out waivers and get helmet fitted
- Watch introductory video
- Receive one-on-one Segway training
- Begin Segway tour of haunted locations
- Visit Iroquois Theater Fire site
- Ride past Marshall Field’s haunted spots
- See mob-run speakeasies and crime scenes
- Hear stories of Al Capone and The Outfit
The Experience
You'll start with a 15-minute arrival window to check in, sign waivers, and get fitted with a helmet. The guide walks you through a one-on-one Segway orientation—even if you've never ridden one, the training is thorough enough that nervous riders leave feeling steady. Once everyone is comfortable, the tour rolls out and the stories begin: the Iroquois Theater Fire, one of the deadliest disasters in U.S. history; Marshall Field's, where staff and visitors have reported ghostly sightings; the sites where The Outfit ran speakeasies and where Antonio Lombardo was assassinated. The route weaves through the city's most infamous locations, and the guide layers in details about Capone's rule, secret tunnels, and the crime scenes that shaped Chicago's reputation.
The Segway itself is the point—you're not walking and stopping, you're gliding through neighborhoods at a pace that lets you take in the architecture and the stories at once. Two hours is long enough to hit the major haunted and mob sites without the day becoming a slog. Tours run in all weather, so dress for the conditions; summer bookings fill fast, so reserve ahead if you're planning a peak-season trip.
What’s included
- Certified Segway tour guide leading the full 2 hours.
- helmet and Segway orientation before departure.
- bag for your personal belongings during the ride.
Operated by Absolutely Chicago Segway Tours
Is this one for you?Book the standard 2-hour tour if you want the full arc of Chicago's haunted and mob history without a time crunch; choose the Halloween Eve or Halloween option if you're visiting during the season and want the atmosphere and crowds that come with it.
Traveler reviews
Compare the 13 similar options
Haunted Chicago Segway Tour: Ghosts & Gangsters★ 4.71 (38)2hENUS$ 75
Chicago Crime Mob Bus Tour: Al Capone, MassacreTour Chicago's crime history on a climate-controlled bus with a live guide—walk crime scenes including the St. Valentine's Day Massacre site★ 4.60 (3,547)1h 30m–2hENUS$ 49View ›
Chicago River Architecture Cruise: 40+ buildings from the waterArchitecture cruise on the Chicago River. See the John Hancock Center, Willis Tower, Wrigley Building and 37 more landmarks. Pet-friendly, full bar.★ 4.84 (16,994)1h–1h 30mEN · ESUS$ 39View ›
Chicago River: 90-Minute Architecture Boat TourChicago River architecture tour covers 130+ years of design on a 90-minute narrated boat ride. Indoor & outdoor seating, professional guide, all three river branches.★ 4.71 (10,933)1h 30mENUS$ 45View ›
Serial Killer & Chicago Landmarks Bus Tour: True Crime HistoryNinety-minute guided bus tour exploring Chicago's true crime history and landmarks like Wrigley Field and the Mag Mile with a live English-speaking guide.★ 5.00 (1)1h 30mENUS$ 46View ›
Chicago River: 45-Minute Architecture Boat TourGlide past Marina City, Wrigley Building, and Merchandise Mart on a 45-minute Chicago River cruise with a local guide. Includes restroom and climate-controlled lounge.★ 4.65 (3,586)45mENUS$ 28View ›
Chicago Skyline Boat Tour: River & Lake Michigan viewsChicago Lake and River Architecture Tour with professional guide, climate-controlled seating and taxes included. Covers 200+ years of architecture.★ 4.69 (2,440)1h 30mENUS$ 45View ›
Chicago: 90-Minute River & Lake Cruise with Skyline ViewsChicago River and Lake Michigan boat tour with Marina City, Wrigley Building, Grant Park, and Field Museum. 90 minutes with live guide. Daily departures, all ages.★ 4.70 (723)1h 30mENUS$ 46View ›
Chicago: Gangster & Ghosts Walking Tour with Speakeasy BarsFeel Chicago’s haunted past on a walking tour with real crime stories, Prohibition speakeasy bars, and exclusive access to historic interiors. Includes expert guide.★ 4.97 (406)1h 30mENUS$ 35View ›
Chicago Flag Bus Tour: city landmarks and historyA 90-minute bus tour through Chicago's landmarks with a live English-speaking guide—learn how Fort Dearborn, the Great Chicago Fire1h 30mENUS$ 42View ›
Chicago: Lake Michigan Sunset Cruise from DowntownDepart near Michigan Avenue Bridge on Wendella's boat, cruise the Chicago River and Lake Michigan at sunset. Climate-controlled lounge, expert guide, restroom. 1.5–2 hours.★ 4.51 (1,689)1h 30mENUS$ 45View ›
Chicago Walking Tour: Loop Architecture & Picasso SculptureDowntown Chicago walking tour of the Loop's landmark buildings, Chagall mosaic, Picasso sculpture and Chicago Theatre. 2 hours, 2 miles.★ 4.98 (245)2hENUS$ 44View ›
Chicago Skyline Boat Tour: 30–45 minute Lake Michigan cruiseLake Michigan skyline cruise from downtown Chicago with narration, onboard bar, and views of Willis Tower, John Hancock Center, Navy Pier.★ 4.44 (950)30m–45mUS$ 34View › 
Top questions
What's the Iroquois Theater Fire and why is it part of this tour?
The Iroquois Theater Fire was one of the deadliest disasters in U.S. history, and the tour passes the site while the guide recounts what happened there and the ghost stories connected to it.
Do I need Segway experience to join this tour?
No. The tour includes a comprehensive one-on-one training session before departure, and the guide ensures every rider—even nervous ones—feels comfortable for the full 2 hours.
What's included in the tour price?
The tour includes a certified guide, helmet, Segway orientation, and a bag for personal belongings; gratuities and hotel pickup are separate.
How many people can book together, and is there a minimum?
Groups are capped at 6 people per booking, and you need at least 2 people to reserve a tour.
What should I know about weight and age requirements?
Riders must be at least 12 years old and weigh between 100 and 260 pounds; the tour is suitable for all fitness levels but is not recommended for travelers with poor cardiovascular health.
Can I book this tour during Halloween?
Yes, the tour runs on Halloween Eve and Halloween itself as a separate option at checkout, though summer dates book quickly—reserve in advance if you're planning a specific date.
Haunted Chicago Segway Tour: Ghosts & Gangsters
2h · EN
from US$ 75 per person
★★★★★★★★★★4.7138 reviews
