Glide through downtown Chicago by Segway and trace the city’s darker chapters — from the Iroquois Theatre tragedy to the Chicago Outfit’s bloody legacy. This compact, two-hour tour pairs easy riding with hard history.
More ways to explore the area's outdoor wonders
You roll out of the shadow of Millennium Park onto the wide sweep of Monroe Street, Segway humming underfoot, as the city’s stone facades lean in with stories. Streetlights and theater marquees throw pools of light across the pavement; your guide threads history and rumor into a steady cadence that keeps the past feeling immediate rather than theatrical.
Difficulty
easy
Duration
2 hours
Fitness Level
Minimal aerobic fitness required; participants should be able to stand and balance for up to two hours and walk short distances.
Wildlife
History
The tour threads together incidents from Chicago’s rapid growth: the Iroquois Theatre fire (1903) influenced national fire-safety codes, while the Chicago Outfit shaped organized crime and civic politics through the 20th century.
Conservation
This is an urban experience—respect historic markers and private property, stay on sidewalks and designated paths, and minimize noise at memorial sites to preserve the experience for others.
Reserve your spot on the Haunted Ghosts & The Chicago Outfit Segway Tour today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Complete the waiver online
Fill out the operator’s online waiver before arrival to avoid delays; arrive 15 minutes early for check-in and helmet fitting.
Wear closed-toe shoes
Sturdy, flat-soled shoes improve balance on the Segway and during brief walking stops.
Bring a light rain layer
Tours run in most weather—ponchos are provided but a breathable, packable rain shell keeps you comfortable.
Avoid alcohol before the tour
Operators may refuse service to visibly intoxicated guests; be sober and steady to participate.
Closed-toe walking shoes
Provides stability on the Segway and during short on-foot stops.
Light rain shell or poncho
Chicago weather can change; a compact rain layer keeps you dry on wet days.
spring
Small daypack
Carry water, your phone, and a light layer without restricting movement.
Fully charged phone with camera
For photos and emergency contact; guides often point out photo opportunities from the Segway.