Top 4 Kayak Trips in Chicago

1.Classic Food & Walking Tour with Free Bike or Kayak

★★★★★★★★★★4.9 · 145 reviews · 3 hours · from $84Our pick

Spend three relaxed hours tasting deep dish, a Chicago dog, Italian beef, brownie or gelato, and Garrett’s popcorn while your local guide leads you through downtown sights. Guides such as Jeff, Julia, James, and Gabe are known for lively city stories. Your ticket also includes a two-hour bike or kayak rental.

“Gabe made it so fun & interesting. Felt very safe. He was great at navigating around crowds, etc. We plan on repeating this tour with friends!!”

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2.Chicago’s Lake Michigan Downtown Kayak Rental at Ohio Street Beach

★★★★★★★★★★5.0 · 22 reviews · 1 to 2 hours (approx.) · from $39Best value

Rent a single or tandem kayak, or a SUP, for one or two hours at Ohio Street Beach beside Navy Pier. You will paddle protected Lake Michigan waters, with the option to stop at nearby beaches and extend your time. Adults rent, while younger riders join with an adult.

“Ethan is a great guy, very helpful. Location is a bit hidden at first. Its off the beach in a trailer to get the registration & waiver done. Once you have the kayak, the lake is pretty much yours explore. Surreal & mesmerizing.”

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3.2-Hour Downtown Kayak Rental

★★★★★★★★★★4.5 · 19 reviews · 2 hours · from $62

You’ll receive an English-language paddling and safety lesson, choose a single or tandem kayak, then follow the Chicago River through downtown’s steel canyons. The small group is limited to six, and the dock sits near Chicago transit and downtown sights.

“The person checking us in and giving us our kayaks gave the worst advice on where to kayak. Also, there were so many dead fish and birds floating and a lot of trash. My husband who ended up finishing it and going the opposite way, said it was much better and cleaner.”

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4.Sunset Kayak Tour on the Chicago River

★★★★★★★★★★4.2 · 5 reviews · 1h 30m · from $57

You will paddle a downtown stretch of the Chicago River during golden hour, passing Willis Tower, the Civic Opera Building, and Merchandise Mart. Wateriders provides the kayak, safety briefing, and English-speaking guide. The small-group format suits beginners with basic swimming skills.

“Eindrückliche Kanu-Tour inmitten von Chicago beim Einnachten… Leider etwas chaotisch organisiert mit Kanus, die viele Reparaturen nötig hätten. Von den Guides keine Hinweise/Erklärungen zur Tour 😳”

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