A Segway tour lets you cover a surprising amount of Chicago's lakefront, parks, and skyline views without walking your legs off. Expect to spend about two hours total: 20-30 minutes on a quick training session, then riding in a small group (usually 6-10 people) at a relaxed pace. You'll roll past Millennium Park, Navy Pier, and parts of the Museum Campus while the guide points out history and architecture. It's smoother than it looks once you get the hang of it, but you will feel a bit silly at first. The experience is mostly outdoors, so weather matters a lot.
Summer is peak season and the most pleasant, especially mornings or early evenings when it's not blazing hot. Spring and fall can be nice if you're okay with wind; winter tours are rare and usually miserable. Expect to pay around $75–$110 per person depending on tour length and group size. Longer skyline-focused tours sit at the higher end.
Tip: Pick a tour that sticks to the lakefront path rather than one that tries to squeeze in downtown streets with traffic. Skip any tour promising you'll "see everything" in under 90 minutes; it's rushed and you'll mostly just follow the leader. Wear comfortable closed-toe shoes and bring a light jacket even in summer—the lake breeze hits hard once you're moving.