Chicago Segway Tour: Mob Stories & Hidden History

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Free cancellationExcellent quality

1/8

Duration2h

GroupUp to 5

LanguagesEN

Mobile ticketAccepted

Two hours on a Segway, four eras of Chicago stories

A two-hour Segway tour of Chicago's downtown and lakefront with a live guide who covers the city's mob past, political history, architectural innovations and lesser-known tales. You glide through Millennium Park, past Cloud Gate and Crown Fountains, through the Lakeshore East neighborhood, along the Chicago River, and to Navy Pier, hearing stories rarely told about the 1968 Democratic National Convention, the Chicago Syndicate, and the city's elite. Training and a helmet are included; minimum age is 12.

Step-by-step itinerary

Explore Chicago's iconic landmarks by Segway

Glide around Millennium Park
See Crown Fountains and Cloud Gate
Pass by notable Chicago buildings
Learn about 2020 skyline addition
Hear stories along the River
Discover history of Navy Pier

The Experience

You start with a thorough training and orientation session before stepping onto your Segway. The guide covers how to balance, accelerate and brake, so even first-time riders move with confidence. Once everyone is steady, the group glides into Millennium Park to see Crown Fountains and Cloud Gate—the Bean—while the guide walks you through what these landmarks mean to the city's reinvention. A bag on your Segway holds your phone, keys and anything else you need to carry.

The route moves through Lakeshore East, the neighborhood that rose in 2020, then follows the Chicago River where the guide stops to share stories about the city's power brokers and the deals made along the water. Navy Pier comes next, and here you learn how this structure shaped Chicago's relationship with Lake Michigan and what it meant to the people who built it. Throughout the two hours, the narration weaves together mob history, the truth behind the 1968 Democratic National Convention, and innovations that changed how cities work—the kind of stories that make you realize how much of Chicago's real past stays hidden from the usual tourist route.

The tour runs rain or shine; ponchos are provided if weather turns. You'll need to wear closed-toe shoes and be comfortable standing for the full two hours. All riders must weigh between 100 and 260 pounds and be able to climb and descend stairs without help. A live guide in English leads every tour, and the pace is set so the group stays together.

What’s included

Professional local guide and live narration throughout the two hours.
thorough training and orientation before the tour starts.
Segway with a storage bag for your belongings.
helmet for safety.

Good to know

Easy physical levelNot for heart conditions

Operated by Absolutely Chicago Segway Tours

Is this one for you?The tour departs from downtown Chicago, so it works best if you're staying near Millennium Park or the lakefront, or if you're comfortable getting to the starting point on your own—the guide covers the city's stories at a pace that keeps everyone together, and the Segway does the legwork so you cover far more ground than walking would allow.