Top 9 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.Moonlight Paddle Tour on the Chicago River

★★★★★★★★★★4.2 · 9 reviews · from $58

Set out after dark with a guide from Wateriders Kayak Tours & Rentals for a 90-minute Chicago River paddle. You’ll receive a safety briefing, use a single or double kayak, and pass Willis Tower and Marina City. Check group size before booking, as one recent outing was much larger than the advertised six people.

“The experience was good, but I didn't feel so safe because of the different motor boats that constantly pass by.”

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5.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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6.Best of Attractions Walking Tour +Bike/Kayak Rental

★★★★★★★★★★5.0 · 5 reviews · 2 hours · from $44

Walk from the Palmer House to the Chicago Water Tower with an English-speaking local guide, stopping at Millennium Park, Cloud Gate, the Chicago Riverwalk, Wrigley Building, and Magnificent Mile. You also receive a free 2-hour bike or kayak rental within three days, weather permitting.

“Bobby’s Bike Hike Tours was amazing! Thanks so much for accommodating my daughter and I on the Chicago Favorites Food & Walking Tour! Our Tour Guide James was very knowledgeable, energetic, and entertaining! This tours is the absolute BEST way to see and taste Chicago!”

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7.Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

★★★★★★★★★★5.0 · 5 reviews · 2 hours (approx.) · from $44

Walk from the Palmer House to the Water Tower with a guide such as Mikey or Mickey, pausing at Millennium Park, the Riverwalk, the Chicago Theatre, and more. Your $44.99 ticket also includes a free 2-hour bike or kayak rental, subject to dates, weather, and seasonal limits.

“I appreciated being able to see the sites. Even more, however, I appreciated learning more about Chicago’s history and people, past and present. Thanks, Mikey, for a great tour. The bonus of the bike rental was also appreciated. We had a nice ride along the lake and even a short visit to the Lincoln Park Zoo.”

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8.History and Architecture Guided Kayak Tour

★★★★★★★★★★5.0 · 3 reviews · 2 hours · from $64

Join a small English-language group of up to six for a two-hour Chicago River kayak tour. Your guide covers the city’s past, engineering feats, drawbridges, wildlife, and skyline views. Single and double kayaks are available, with equipment included.

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9.Chicago in a Day: Food & Walk Tour+Free Bike or Kayak Rental

★★★★★★★★★★4.2 · 3 reviews · 5 hours · from $99

Spend five hours walking Chicago with an English-speaking local guide, tasting deep dish, a hot dog, Italian beef, brownie, and Garrett’s popcorn. See the Riverwalk, Millennium Park, Cloud Gate, and more, then use your included two-hour bike or kayak rental within three days.

“We had a terrific time exploring the food and city with an excellent guide.”

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