11 Chicago Kayak Tours Worth an Afternoon

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

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

Walk downtown with a local guide, stopping for deep-dish pizza, a Chicago hot dog, Italian beef, Garrett’s popcorn, and a sweet finish. The route links landmarks such as Millennium Park, Cloud Gate, the Riverwalk, and the Chicago Theatre on daytime tours. Your ticket also includes a two-hour bike or kayak rental, subject to seasonal and schedule limits.

“Our guide Jeff was incredibly knowledgeable, not only about the food we tried but about the history of the city, as well as the architecture. Jeff kept things moving and very upbeat throughout! I would rate Jeff as a five star guide! My husband and I just finished a two week tour of Greece and had many great guides during that time but Jeff was by far the best! Thank you Jeff from Rob and Shannon.”

Check availability →Read our full review

2.Starved Rock State Park: Guided Kayaking Tour

★★★★★★★★★★4.9 · 26 reviews · 2 hours · from $74

Launch from Kayak Starved Rock Campground for a guided two-hour paddle along the Illinois River, below Starved Rock’s sandstone bluffs and beside shoreline canyons and lotus plants. Guides such as Rich, Matt, and Dave mix local history with jokes. Kayaks, paddles, and life jackets are included. Bring waterproof shoes; dogs can join in a tandem kayak.

“Rich and Matt were great guides! We had so much fun! Would definitely come again”

Check availability →Read our full review

3.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, from Ohio Street Beach beside Navy Pier. Paddle Lake Michigan at your own pace, with a chance to stop at a nearby beach or extend your rental. Staff members named Evan, Ethan, and Mau have helped paddlers get started.

“I sat on the rock ledge while my 17 year old grandson kayaked from Ohio Street Beach. It was awesome to see him out with the yachts on Lake Michigan, and was a great event to end our five days in Chicago!”

Check availability →Read our full review

4.2-Hour Downtown Kayak Rental

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

At the downtown Chicago River dock, Wateriders Kayak Tours & Rentals provides a paddling lesson, safety briefing, and a two-hour kayak rental. Choose a single or tandem kayak, then paddle among the city’s skyscrapers. The group is limited to six, and the activity is led in English.

“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.”

Check availability →Read our full review

5.Tandem Guided Kayak Tour Near Chicago

★★★★★★★★★★4.5 · 6 reviews · 2 hours (approx.)

Set out from Kayak Starved Rock Campground for an approximately two-hour guided tandem kayak tour on the Illinois River. Guides such as Rich and Dave lead the way past towering St. Peter’s sandstone bluffs, with chances to spot bald eagles, pelicans, and lotus flowers. Kayaks, paddles, and life jackets are included.

“Rich and his partner were the best tour guides! We had so much fun and saw so many great things! We would totally recommend this trip!”

Check availability →Read our full review

6.Sunset Kayak Tour on the Chicago River

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

Join Wateriders Kayak Tours & Rentals for a 90-minute guided paddle through downtown Chicago at golden hour. You’ll pass Willis Tower, the Civic Opera Building, and Merchandise Mart in a small group of up to six. Kayak rental and a safety briefing are included. Bring water, sunscreen, comfortable clothes, and a camera.

“This was a fun activity that puts you right in the middle of Chicago! All of the guides are great and take their time to make sure you are comfortable before the fun starts. Highly recommend!”

Check availability →Read our full review

7.Best of Attractions Walking Tour +Bike/Kayak Rental

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

Walk from the Palmer House through the Loop, Millennium Park, Cloud Gate, the Chicago Theatre and along the Riverwalk toward the Water Tower. Your English-speaking local guide shares city history and current context. The $44 tour also includes a two-hour bike or kayak rental to use within three days, subject to seasonal and weather limits.

“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!”

Check availability →Read our full review

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

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

This two-hour Chicago walk runs from the Palmer House Hilton to the Historic Water Tower, with stops for Millennium Park, the Riverwalk, the Chicago Theatre and more. Expect a guide-led history lesson for up to 18 people, plus a free two-hour bike or seasonal kayak rental to use within three days of your tour.

“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.”

Check availability →Read our full review

9.Single Guided Kayaking Tour near Chicago

★★★★★★★★★★5.0 · 4 reviews · from $69

Meet at 1170 N 27th Rd in Ottawa for a two-hour guided kayak tour near Starved Rock. You’ll start with a land-based lesson and safety briefing, then paddle beneath St. Peters sandstone bluffs, watching for bald eagles, white pelicans, herons, turtles, and American lotus flowers. A guide called Turtle Rick has been noted for his personable manner and knowledge of the area.

“We ended up with beautiful weather, and our guide "Turtle Rick" was very knowledgeable about the area as well as personable.”

Check availability →Read our full review

10.History and Architecture Guided Kayak Tour

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

Wateriders Kayak Tours & Rentals leads a two-hour, English-language paddle through downtown Chicago for groups of up to six. You’ll use a single or double kayak, pass beneath distinctive ironwork bridges, see the skyline and riverfront, and hear how the river helped shape the city, including why it flows in reverse.

Check availability →Read our full review

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

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

Spend five hours walking downtown Chicago with a local guide, stopping for deep-dish pizza, a Chicago-style hot dog, Italian beef, brownie, and Garrett’s popcorn. You’ll pass Millennium Park, Cloud Gate, the Riverwalk, and more. Your ticket also includes a two-hour bike or seasonal kayak rental, valid within three days.

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

Check availability →Read our full review