Many years ago, when I moved from Seattle back to Chicago, I was looking for more outdoor activities. Kayak tours were something I did a few times on vacation in cool places like Maine or Hawaii, but I hadn’t given it much thought as a regular hobby. Luckily, I found Chicago Kayak, a great kayaking club in Evanston, and thus began a several-year affair with the waterways of Chicago. Opportunities to kayak Chicago continue to grow, as more access points open up and more outfitters offer Chicago kayak rentals and tours. After spending at least a decade kayaking around Chicago, I have compiled a list of the top ten places to go kayaking in Chicago.

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A note of caution: I was taught to always take Chicago kayaking very seriously. Kayaking Lake Michigan especially is not to be taken lightly. Weather and waves can change quickly, and water temps can be deceiving on a hot summer day. Always make sure you are prepared with proper clothing and paddling skills. Don’t end up on the evening news!

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Top Ten Chicago Kayaking Spots

• Downtown – Chicago River
• Leone Beach – Lake Michigan
• Winnetka – Lake Michigan
• Illinois Beach State Park – Lake Michigan
• Skokie Lagoons
• Busse Woods
• Chain of Lakes State Park
• Indiana Dunes National Park
• Des Plaines River
• Yorkville Whitewater Park

Chicago River Kayaking

Chicago River kayaking gets the nod for most interesting and most improved over the years. When I first kayaked the Chicago River through downtown in 2008, there was nowhere to exit your boat between the Chicago River north branch boat launch at Rockwell (way up north!) and Navy Pier at Lake Michigan. If you had to use the restroom, you had to hold it until we got out into the non-sewage waters of Lake Michigan and then go for a freezing swim. Today, the Chicago Riverwalk adds a whole new level of fun to kayaking the Chicago River. You can stop for a beer or bite at one of many establishments and you can even paddle through the Chicago River locks out into Lake Michigan, or paddle south of the city and visit Chicago’s Chinatown for some dim sum!

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Lake Michigan Kayaking – Leone Beach

Leone Beach, on the north side of the city near Loyola, is a favorite spot to launch a Lake Michigan kayak outing. I led many full moon paddles out of Leone Beach, where we would paddle south towards the city, watch the lights of downtown start to twinkle, and then head back to the beach as the full moon rises over Lake Michigan.

Extra caution is required for kayaking at dusk! Make sure you have the right gear, including waterproof lighting on your boat!

Lake Michigan Kayaking – Winnetka

Another favorite Lake Michigan kayak spot is at the Lloyd Beach/Boat Launch just south of Tower Road Beach in Winnetka. Since I worked in the northern suburbs, this was a great spot for an after-work paddle in the evenings. Lloyd Beach has a nice sandy beach, with a breakwater that makes entry and exits a bit easier. If you like to gawk at huge lakefront mansions and try to guess which CEO or NBA player lives there, this is the paddle for you!

Illinois Beach State Park

Illinois Beach State Park is a bit of a drive from the city, but it’s well worth it if you have the time. You can even stay overnight at the campground or at Illinois Beach State Park resort! We had some fun outings here with a potluck at the picnic sites after a day of paddling. They are pretty strict about closing times, so keep an eye on your watch and make sure you are back in time to get off the beach. It’s a bit of a long carry to the water, so it’s good to have friends along for this one! This is more of a nature experience and you’ll paddle along the dunes of the state park, but you’ll still see boat traffic from nearby marinas.

Skokie Lagoons

Skokie Lagoons in Winnetka is where I really learned to kayak and it’s a great place for beginners or for seasoned paddlers looking to practice rescue skills. Chicago River Canoe & Kayak rents kayaks and canoes at the Lagoons and holds special tours throughout the year, such as a sunset dinner paddle. This is a great backup spot if the waves, wind, or water temperature on Lake Michigan are not conducive to kayaking. There are many hidden spots to explore in the lagoons, and lots of wildlife to see as well. Just pay attention to where the dams are (they are well signed) and don’t paddle near them!

Busse Woods

Busse Woods is another great beginner location for kayaking near Chicago. Located in Schaumburg not far from Woodfield Mall, Busse Woods Forest Preserve is popular for walking and biking, but I rarely saw other kayakers out on the water. While it may be a deterrent for some, I loved that Busse Woods is in the O’Hare flight path and you can see lots of planes coming in for a landing. It does disrupt the peace a bit, but I do love watching planes!

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Chain of Lakes

Paddling around the Chain of Lakes in northern Illinois is a fun adventure, but you should note this is also a huge party spot for boaters, so you have to be super careful around the motorboats and jet skis. It’s best done on a weekday or in the shoulder seasons. That said, you can roll your kayak right up to any number of bars and restaurants along the lake, and make a day of it!

Indiana Dunes National Park

Indiana Dunes National Park is a great day tour from Chicago and one of the newest National Parks in the Midwest! My first visit to the beach at Indiana Dunes did not leave a good impression, as I found the beach to be crowded and dirty. However, paddling there was an entirely different experience. We launched from the State Park side and had great views of the dunes as we paddled around the shore and up a nearby river. There is also great hiking in the area, plus camping too if you want to make it an overnight trip! Don’t forget to buy a National Parks Pass before you go!

Des Plaines River

If you prefer a river paddle along a water trail, the Des Plaines River has several options in the northern suburbs of Chicago. In the far north, you can have a very quiet, nature experience, while segments closer to the city offer a more urban experience. There are many sections to paddle, but there are also dams along the way so you have to research your launch and takeout ahead of time. Every May, you can join the Des Plaines River Canoe & Kayak Marathon, and for many years a local kayak club organized a New Year’s paddle on the Des Plaines River. I am a fair-weather paddler, so I never did that one!

Yorkville Whitewater Park

Did you know that Chicago has a whitewater park? Technically, the Marge Cline Whitewater Course is in Yorkville, about an hour from the city. But it’s pretty cool! Even if you don’t kayak, it’s fun to come to see all the boaters playing in the waves. You’ll see little whitewater boats, canoes, and regular kayaks. It’s a pretty short run, so you get your exercise shuttling your boats back up, but you can run the waves as many times as you want! The Yak Shack has plenty of rentals and gear if you don’t have your own.

More Kayaking Near Chicago

A few other places that get an honorable mention for kayaking near Chicago are Nippersink Creek, which I never got to paddle myself. Water levels are finicky, so the timing never worked out. In the western suburbs, the Du Page River is a great casual paddle. Farther afield, the Rock River and Kishwaukee Rivers near Rockford, as well as Rock Cut State Park, have nice scenery and fewer crowds than you’ll find in Chicago.

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Chicago Kayak Rentals

Kayak rentals on the Chicago River are a great way to try kayaking without committing to an expensive investment in equipment. These Chicago kayaking shops offer rentals, private tours, and guided tours. Make sure to call ahead on busy summer weekends to ensure they have availability. Need a gift idea for an outdoorsy Chicago friend? Gift certificates for these outfitters are perfect!

• Urban Kayaks has two locations: one on the Riverwalk and another at Monroe Harbor on Lake Michigan. Tours include a Historic Chicago Tour, Sunset Tour, Moonlight Paddle, and paddleboarding classes. They even offer a season pass, which is a great option for city dwellers who don’t have room to store a kayak!
• Wateriders has locations at Rockwell, Bridgeport, and the East Bank Club. Tour options include a fireworks paddle on the lake shore at Navy Pier, an Architecture tour, a sunset paddle, and a moonlight paddle.
• Kayak Chicago has three locations to rent kayaks: Chicago River near Goose Island and North Ave, as well as locations on Lake Michigan at Montrose Beach and North Avenue Beach.

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