Chicago Segway Tour: Grant Park, Riverwalk & Lakefront Ride

Summary

Glide past buckingham fountain and riverwalk sights with a chicagoan guide

You’ll zip through downtown Chicago on a Segway with a local guide who knows every shortcut and story. Glide past Grant Park, Buckingham Fountain, and along the lakefront or Riverwalk — even catch Navy Pier from afar. Expect small surprises (like street music or city smells) and plenty of laughs as you see Chicago from an entirely new angle.

What’s the experience like?

The first thing I noticed was the quiet whir of the Segway under my feet — honestly, I was nervous I’d wipe out in front of everyone. But our guide, Marcus (he’s lived here his whole life), just grinned and told us to relax, “Chicago’s got your back.” We started near Grant Park, where the grass smelled sharp after last night’s rain, and zipped by Buckingham Fountain. The spray caught the morning light and for a second it felt like we were in some old movie set. I kept thinking how different everything looks when you’re gliding instead of walking — even the pigeons seemed to give us side-eye.

We rolled past families setting up picnics, joggers waving at Marcus (he knew half of them), and this one street musician playing something bluesy by the lakefront. The city sounds — sirens somewhere distant, laughter echoing off glass buildings — mixed with that weirdly satisfying hum from our wheels. At one point, Marcus pointed out a spot near Museum Campus where he used to sneak out as a kid to watch fireworks. He made us stop so we could see Navy Pier in the distance — kind of hazy but still unmistakable. It’s funny how you can live in a place or visit it ten times but miss all these little stories.

I picked the Riverwalk route because I wanted to see those famous Chicago bridges up close (they really do look like something out of a comic book). We passed Millennium Park too — there was a wedding photo shoot happening and for a second I almost crashed trying not to photobomb them. The wind off the river was colder than I expected; should’ve brought gloves. But honestly, that just made the hot dog stand smell even better when we finally stopped for a break. Two hours went by fast — maybe too fast? Still thinking about that view over Michigan Avenue as we headed back.

Step-by-step itinerary

Day 1 — 2-hour guided Segway tour in Chicago

• Begin Segway tour with guide
• Glide through downtown Chicago
• Explore Grant Park and Buckingham Fountain
• Visit Museum Campus and lakefront
• Option to tour Chicago Riverwalk
• View Navy Pier and Chicago bridges
• Travel up Michigan Avenue
• Pass by Millennium Park
• End tour with memorable experience

Top questions

How long is the guided Segway tour in Chicago?

The guided Segway tour lasts 2 hours.

Which Chicago landmarks are included on this tour?

You’ll see Grant Park, Buckingham Fountain, Museum Campus, Riverwalk, Navy Pier (from a distance), Michigan Avenue, and Millennium Park.

Is this Segway tour suitable for beginners?

Yes, it’s suitable for all physical fitness levels and includes instruction from an experienced guide.

Does this tour include pickup?

No hotel pickup is included; you meet at the starting location in downtown Chicago.

Are pregnant travelers allowed on this Segway tour?

No, it’s not recommended for pregnant travelers.

Can I use public transportation to reach the meeting point?

Yes, public transportation options are available nearby.

What are my route options for this Chicago Segway tour?

You can choose between touring Grant Park/lakefront or taking the Riverwalk route up Michigan Avenue.

What’s included

Your day includes a 2-hour guided Segway ride through downtown Chicago with an experienced local guide leading you past major sights like Grant Park, Buckingham Fountain, Museum Campus or along the Riverwalk toward Navy Pier—routes are flexible depending on your preference before heading back together at the end.