Chicago Lakefront Segway Tour: Parks, Skyline & Museum Stops

4.58

(145 reviews)

What’s the experience like?

Honestly, I was a little nervous about getting on a Segway for the first time — I’m not exactly graceful. But our guide (her name was Tasha) had us rolling outside the shop within ten minutes, laughing at my wobbly start. The air off Lake Michigan felt sharp but fresh, and you could smell popcorn from some vendor carts even though it was barely noon. We zipped along the Chicago Lakefront Trail and I kept catching myself grinning at how easy it was to move — way more fun than I expected.

Tasha knew every shortcut through Grant Park, pointing out where locals play chess under the trees or just nap in the sun. At Buckingham Fountain, she told us a story about her uncle proposing there back in the 80s — apparently it’s “a thing” for Chicagoans. The water sparkled so much I squinted; someone’s dog barked at our little convoy and made half of us jump. We stopped by Millennium Park too — yes, we did the Cloud Gate selfie (I look ridiculous in mine), and then coasted over to Soldier Field. It’s wild seeing that stadium up close instead of just on TV.

I didn’t expect to feel so connected to Chicago by gliding through its parks like this. When we paused outside the Field Museum, Tasha pointed out where Máximo the Titanosaur stands inside (you can actually see him through one window if you lean just right). There were families everywhere — kids squealing about dinosaurs or pretending to be explorers. The whole ride felt like being part of city life instead of just watching it go by. I still think about that view back toward downtown as we headed home; something about sunlight bouncing off glass buildings and water together gets stuck in your head for days.