Answers from Our Experts (1)
I’ve mentioned it many times, but it’s still my favorite: The best way to float down the Chicago River is with the Chicago Architecture Foundation's architectural boat tour, which runs during the warm months. The 90-minute tour takes you through the heart of the city with unparalleled, up-close views of the skyscrapers, and the water is calm and true-blue beautiful.
If you’d rather get out onto Lake Michigan, there are dozens of opportunities to cruise with or without a guide, or even in a speedboat. Wendella Boat Tours is a trusted family-owned operation that’s been around for decades, offering a handful of different ways to cruise the lake and river.
Though I’ve never signed up for a tour, I’ve heard great things about Kayak Chicago, which offers all kinds of tours exploring both the serene Chicago River and the more adventurous Lake Michigan. Kayak Chicago does individual rentals, too, for more experienced paddlers who want to go out on their own.