Chicago Segway Tour: Mob Stories & Hidden History

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.

Before you book

Days and timesNext departure: 20 Apr 2027

Book up to12h before

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

GroupUp to 5

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.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated 2 days ago

Good to know

Low physical effortNot recommended with heart problems

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.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What stories does the guide tell on the Chicago Segway tour?

The guide covers Chicago's mob history, the 1968 Democratic National Convention, the city's political elite, and architectural innovations that changed urban design: stories that are rarely told on standard tours.

Do I need experience to ride a Segway on this tour?

No experience is necessary. The tour includes a thorough training and orientation session before you start, so first-time riders learn to balance and control the Segway before the group moves out.

What's included in the two-hour tour?

The tour includes a professional local guide, live narration, a Segway with a storage bag, a helmet, and the training session. Ponchos are provided if it rains.

Can children ride on this Segway tour?

Yes, children can ride if they are at least 12 years old and weigh between 100 and 260 pounds. Anyone under 18 must be accompanied by a guardian.

What neighborhoods and landmarks does the tour cover?

The tour covers Millennium Park (including Cloud Gate and Crown Fountains), the Lakeshore East neighborhood, the Chicago River, and Navy Pier, gliding along the lakefront and downtown as the guide shares stories about each area.

What should I wear and bring on the Segway tour?

Wear comfortable closed-toe shoes and dress for the weather. The tour operates in all conditions and ponchos are provided if it rains. Bring your phone and keys. The Segway has a bag to store personal items.