If you’re planning a trip to Chicago and want to see plenty without exhausting yourself, a Segway tour of the city’s key sights might just be your best bet. We’ve come across this highly-rated, small-group experience and thought it’s worth sharing what makes it stand out — and what to keep in mind.
What we love about this tour is how it combines fun transportation with educational stops, letting you cover a good chunk of the city in just a couple of hours. Plus, it’s capped at eight people per guide, which means you’re not lost in a crowd and get plenty of personalized attention. The fact that it’s beginner-friendly also makes it accessible to most, even if you’ve never ridden a Segway before.
One thing to consider is that the tour runs rain or shine and is weather-dependent, so it might be a good idea to dress accordingly. Also, the price of $70 per person is reasonable, considering how much ground you cover and the guided experience you get, but it’s worth noting that food and drinks are not included. This tour is perfect for first-time visitors who want a lively, quick overview of Chicago’s most famous spots.
If you enjoy a mix of sightseeing, light adventure, and engaging guides, then this tour could be a fantastic way to kick off your Chicago adventure. It’s especially suited to those who want to maximize their sightseeing time with a bit of fun — and a bit of glide.
Key Points

- Efficient sightseeing: Cover 7-8 miles of Chicago’s highlights in just 2 hours, saving time and energy.
- Small group: Max of 8 travelers ensures personalized guidance and a more relaxed experience.
- Beginner-friendly: Easy-to-ride Segways and comprehensive training make this accessible for most.
- Stunning views: Glide along the lakefront, past iconic landmarks and city skylines.
- Value for money: For $70, you get a guided tour, equipment, helmets, and a memorable experience.
- Ideal for first-time visitors: It’s a great starter tour to get your bearings and see the city quickly.
What to Expect on the Tour
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Starting Point and Check-in
Your adventure begins at 300 E Monroe St, right in the heart of downtown Chicago. Arriving 15 minutes early helps with check-in, waiver signing, and getting fitted for your helmet. The staff is friendly and professional, making the initial setup feel smooth and straightforward.
Guided Segway Training
Before hitting the streets, you’ll get a quick, friendly training session. We’ve read reviews praising guides like Clark and Tammy for their patience and clear instructions, even for nervous first-timers. You’ll practice balancing and steering, and once confident, you’re ready to roll.
The Landmarks and Stops
- Buckingham Fountain: This is a Chicago icon, with its impressive water display and scenic location in Grant Park. Posts here last about 10 minutes, enough for photos and a quick look.
- Soldier Field: Home of the Chicago Bears, it’s a stadium with a significant sports history. You’ll see it up close and learn a bit from your guide.
- The Field Museum and Shedd Aquarium: Gliding past these cultural landmarks, you get a glimpse of Chicago’s educational and entertainment hotspots. Although you don’t go inside, the exterior views and commentary make it worthwhile.
- Lakefront: For about 30 minutes, you’ll cruise along Lake Michigan’s shores, enjoying stunning skyline views and photo opps. Multiple reviews highlight how memorable and scenic this part is, with many commenters noting how perfect the backdrop is for pics.
The Experience
Throughout, guides share tidbits and fun facts about the city, from architecture to sports. Guests consistently mention how engaging and knowledgeable their guides are, making the tour both fun and informative. Several reviews mention guides like Marshall, Jeremy, and Matt, who go above and beyond with their patience and stories.
Practicalities
The whole tour lasts about 2 hours, making it a manageable and enjoyable activity. The group size ensures you’re not rushed, yet it’s quick enough not to overextend your sightseeing day. Since helmets and training are included, there’s no extra hassle, and the price feels fair for the experience.
The Value of This Tour

While $70 might seem a little steep if you’re watching your budget, keep in mind what you’re getting: a fun, guided, and scenic overview of Chicago that’s suitable for most fitness levels. It’s especially appealing for first-time visitors who want a quick, engaging way to orient themselves. Many travelers say this tour helps you decide what attractions to explore more deeply later, making it a smart starting point.
Reviewers also highlight how easy it is to learn riding a Segway, even if it’s your first time. The professional guides are praised for their patience, with Wendy J sharing that her daughter, initially nervous, was helped along by a very patient Marshall. This kind of support makes the whole experience feel comfortable rather than intimidating.
Who Would Love This Tour?

This experience works beautifully for travelers eager to see a lot of Chicago in a short time, especially if they like a touch of adventure. It’s perfect for first-timers, groups of friends, or couples wanting to add some fun to their trip. If you’re traveling with family members over 12 who can stand unassisted and weigh at least 100 lbs, this could also be a fun activity for most.
However, those who dislike outdoor activities or have mobility issues might want to consider other options, as this tour requires standing and some basic physical activity.
FAQs
Is this tour suitable for beginners?
Absolutely. The tour is designed to be beginner-friendly, with a full training session beforehand to ensure everyone feels comfortable riding the Segway.
How many people are in each group?
The tour is capped at 8 travelers per guide, providing a more personalized experience and plenty of attention.
What should I wear?
Dress for outdoor activity—wear close-toed shoes and layers depending on the weather. Ponchos will be provided if it rains.
Can kids join?
Children must be at least 12 years old, and should be able to stand unassisted for the duration of the tour.
What is the minimum and maximum weight allowed?
Participants should weigh at least 100 lbs (45.5 kg) and no more than 260 lbs (118 kg).
What’s included in the price?
The tour price includes a professional guide, helmet, Segway use, and training.
Are food or drinks included?
No, food and drinks are not included in the tour price.
What happens in bad weather?
The tour operates in all weather conditions, but if weather causes cancellation, you’ll be offered a different date or a full refund.
How long is the tour?
It lasts approximately 2 hours, covering about 7-8 miles of city sights and Lake Michigan.
Where do I meet for the tour?
At 300 E Monroe St, Chicago, easily accessible downtown.
Chicago Landmarks & Museum Campus Small Group Segway Tour
“This Segway tour was amazing! Our tour guide, Clark, was informative and funny. We enjoyed our tour!”
Final Thoughts

If you’re looking for an engaging way to check out Chicago’s top sights without overexerting yourself, this small-group Segway tour hits the mark. The combination of scenic lakefront views, iconic landmarks, and expert guides ensures your experience is both memorable and informative. Plus, the limited group size means it’s personal enough to feel special.
This tour is particularly well-suited for those new to the city, families with older kids, or anyone wanting a quick, fun overview of Chicago’s most famous spots. The price offers good value, especially when you consider how much ground you cover and the quality of the guides. Just remember to dress appropriately for the weather, and arrive a bit early for check-in.
Overall, it’s a lively, upbeat way to kick off your visit or break up a busy sightseeing schedule. Whether you’re snapping photos along the lake or learning fun facts about Soldier Field, you’ll walk away with plenty of great memories — and a big smile.
Happy sightseeing, and enjoy your time in the Windy City!
More Museum Experiences in Chicago
- Chicago: American Writers Museum Flexible Date Entry Ticket
- Chicago : The Field Museum Skip the Line 2H Guided Tour
- 2-Hour Chicago Lakefront & Museum Campus Segway Tour
- Chicago: Lakefront, Parks, and Museums E-Bike Tour
- Volo Auto Museum: Admission Ticket
- Lincoln Park Nature Museum and Zoo Public Walking Tour
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