Chicago Bike & Segway Tours — Lakefront Trail & City Routes Compared
Chicago's flat lakefront trail is made for two wheels — the choice is a guided bike tour, a food-tasting bike tour, a Segway tour, or a self-guided rental.
Available
4 options
Avg. rating
4.7 - 3,842 reviews
From
$60 USD
Cancellation
Free up to 24h before
Bike & Segway Tours: what to know before booking
Chicago's flat lakefront trail is made for two wheels — the choice is a guided bike tour, a food-tasting bike tour, a Segway tour, or a self-guided rental.
- Availability
- 4 ticket options compared
- Starting price
- Tickets currently start around $60 USD before checkout fees.
- Rating signal
- Compared options average 4.7 stars across 3,842 traveler reviews.
- Location
- Most tours and rentals start near Millennium Park, the Riverwalk, or the lakefront
- Best time
- Morning for calm trails, or a sunset Segway tour for the skyline as it lights up
- Ticket note
- Date- and time-specific; arrive 15 minutes before departure for training and fitting
Bike & Segway Tours in Chicago
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Everything you should know before you book
Chicago's 18-mile Lakefront Trail is flat, scenic, and almost entirely car-free, which makes it ideal for biking. Guided bike tours roll past Grant Park, Museum Campus, and Navy Pier with a guide setting the pace, while food-tasting bike tours add stops for the city's signature bites between stretches of riding.
Segway tours are the lowest-effort way to cover the lakefront. Every tour starts with a short training session, then sticks to wide paths along the lake and through the parks. Prefer to go solo? Bike rentals let you set your own route, and the lakefront is hard to get lost on.
Frequently asked questions
Is biking in Chicago easy for beginners?
Yes — the Lakefront Trail is flat and separated from traffic, so it suits casual riders. Guided tours set an easy pace and stop often for photos.
Is a Segway tour beginner-friendly?
Yes — every Segway tour begins with a training session, and routes stay on wide lakefront paths and park trails away from traffic.
How long are the tours?
Most bike and Segway tours run 2–3 hours along the lakefront and through the parks. Food-tasting bike tours run longer to allow for the stops.