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.

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.

Before you book

Days and timesNext departure: 3 Jun 2027

Book up to8h before

AgesAdult (12 and older) · Under 12: can't be booked

GroupUp to 8

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated yesterday

Good to know

Low physical effortNot recommended with heart problems

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.

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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.