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Discover Chicago from a fresh perspective on this 1.5-hour sunset Segway tour, exploring top landmarks with expert guides for just $75 per person.

The Chicago Sunset Segway Tour offers a unique way to see the city’s iconic landmarks in just 1 hour and 30 minutes. For $75 per person, this small-group adventure takes you through some of Chicago’s most notable sights, all while riding a Segway, making it accessible even for beginners. With just 10 people per tour, the experience feels personal and relaxed, perfect for those who want to explore without the fatigue of walking or the hassle of vehicle traffic.
Starting at 34 S Michigan Ave, the tour begins at 5:30 pm, coinciding with the sunset, which means you’ll witness Chicago’s skyline transform as lights come on. The tour includes comprehensive instruction and helmet use—so no prior experience is necessary. While the tour does not include hotel pickup or meals, its focus on sightseeing and the small group size make for an intimate and engaging experience.

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This tour kicks off at 34 S Michigan Ave, right in the city’s downtown area. The meeting point is easy to access, and the tour begins at 5:30 pm, aligning with the late afternoon glow that turns Chicago’s skyline into a picturesque backdrop.
This starting location allows you to immediately learn about the city’s vibrant atmosphere. Since hotel pickup and drop-off are not included, visitors should plan to arrive on time. The focus remains on the sightseeing experience, with all necessary gear, including helmets, provided by the tour operator Bike and Roll Chicago.

One of the most praised aspects of this tour is the comprehensive instruction. The guides are known for their patience and clear explanations, making it straightforward for first-timers to get comfortable on a Segway. The guides also share interesting stories and local insights, which enrich the sightseeing experience.
For those worried about maneuvering, the easy-to-learn nature of the Segway makes it accessible to any age within the age range of 12 and up, and a weight limit of 100 to 260 lbs. Pregnant women are advised not to participate, but most people find the activity enjoyable and manageable.

Throughout the 90-minute ride, the tour visits several of Chicago’s most renowned landmarks:
The stops are carefully chosen to showcase the richness of Chicago’s architecture, sports history, and lakeside beauty, all while the twilight enhances the visual appeal.

Riding through Chicago as the sun sets offers a special atmosphere. The city lights start to twinkle, and the skylines glow against the evening sky, making for great photo opportunities. The fountains and lakeside views are particularly captivating during this time, creating a sense of calm and wonder.
The hour and a half duration allows ample time to enjoy these sights without feeling rushed. The guided narration adds context to each stop, making the experience both fun and educational.
Reviews highlight guides like Andre, Vincent, Lola, and Alicia for their knowledge, patience, and enthusiasm. They share local stories, Chicago history, and personal insights that make each stop meaningful.
Guests appreciate guides who personalize the experience, assist with photography, and ensure everyone’s safety. Their friendly demeanor contributes greatly to the overall enjoyment of the tour.
The tour is suitable for most people aged 12 and above who weigh between 100 and 260 lbs. Riders must be comfortable standing and balancing on the Segway for the duration. Pregnant women are not permitted to participate.
Since the tour involves riding a Segway, participants should be prepared for some physical activity, but the easy learning curve ensures most can manage. Weather conditions can affect the experience; if it’s too dangerous to ride, the tour may be canceled or rescheduled.

The tour is weather-dependent. Bad weather such as heavy rain or storms can lead to cancellations. In such cases, the operator offers a full refund or rescheduling options. It’s advised to check the forecast before booking to ensure a smooth experience.
Reservations are typically made 13 days in advance, ensuring availability during peak times. The free cancellation policy allows full refunds if canceled more than 24 hours before the start. Cancellations within 24 hours are non-refundable, so planning ahead is wise.
Since the tour is limited to 10 participants, booking early is recommended to secure a spot, especially during busy seasons or sunset times.
What sets the Chicago Sunset Segway Tour apart is its combination of accessible riding, personalized group size, and the opportunity to see Chicago’s landmarks during the magical sunset hour. It appeals to those looking for a fun, unique, and informative way to explore the city.
The tour’s focus on top attractions like Millennium Park, Buckingham Fountain, and the Museum Campus offers a well-rounded experience in a compact time frame. It’s perfect for visitors who want to cover a lot of ground without tiring themselves out.
This tour is ideal for first-time visitors eager to see Chicago’s highlights, families with older children, or anyone interested in trying a new way to explore the city. Because of the easy instruction, it welcomes beginners and those who might be hesitant about riding a Segway.
Sunset views and small-group intimacy make it especially suited for those who appreciate scenic photos and personal attention. It’s a great option for groups wanting a laid-back, visually striking city tour.
The $75 investment provides a memorable experience through Chicago’s most iconic spots at a beautiful time of day. The combination of expert guides, easy Segway riding, and stunning sunset scenery delivers great value for the duration.
While it doesn’t include meals or transportation from hotels, the focused sightseeing and small group setup create a relaxed, engaging atmosphere. This tour represents a fun, practical way to appreciate Chicago’s skyline, lakeside beauty, and architectural treasures.
“Great tour guide.very knowledgeable . Beautiful lakeside tour!!! Buckingham fountain was breath taking!”
Is the Chicago Sunset Segway Tour suitable for beginners?
Yes, the tour includes comprehensive instruction and easy-to-maneuver Segways, making it accessible for beginners of any age (12 and older).
What landmarks will I see during the tour?
You will visit The Field Museum, Adler Planetarium, Soldier Field, Buckingham Fountain, and Millennium Park, along with lakeside views at sunset.
How long does the tour last?
The tour runs for approximately 1 hour and 30 minutes, offering a relaxed pace that covers multiple sights without feeling hurried.
Are there any physical restrictions?
Participants should weigh between 100 and 260 lbs and be comfortable standing on a Segway. Pregnant women are not allowed to join.
What happens if the weather is bad?
The tour may be canceled if the weather makes riding unsafe. In such cases, a full refund or rescheduling is offered.
How far in advance should I book?
Most bookings are made about 13 days ahead, but early booking is recommended, especially during peak sunset times or busy periods.