Best Places for Kayaking in the Chicago Area

Only an hour and a half from the city, paddling on the Fox River offers a perfect day or weekend getaway. My overnight trip on the Fox River was a surprising delight. The cliffs and towering foliage that line the narrow river create an illusion of otherworldliness — a total oasis from bustling city life. The river’s gentle current makes it perfect for families or groups looking for a leisurely paddle. My friends and I lucked out with clear skies and warm weather, and were able to kick back and float our way down most of the route, soaking up the warm sun and cool waves. 

Overall, the river is very shallow, with plenty of areas along the way for picnicking, recreation, or camping. There are dedicated campgrounds with reservable sites, but we opted to camp along the river instead and I can’t recommend it enough. Rather than squeezing between other campers in a typical drive-in campsite, we chose to explore the riversides and picked a gorgeous and secluded spot to set up camp.

There are several convenient spots to pitch a tent, and we ended up with a pretty perfect site that gave us sweeping views of the river and an abundance of beautiful foliage. You need to bring all your camping gear along for the ride, but it’s worth the extra work to experience a night here. The rocky ground makes for a less-than-comfortable sleep though, so pack a mat or inflatable. 

This river provides the perfect antidote to city burnout. It’s close enough for an afternoon trip if you’re not wanting to spend the night, but the beautiful riverside camping makes this an ideal overnight option for weekenders. The Fox River also has a rich history, and floating down these waters can leave you in timeless awe. Famous French explorers Rene-Robert Cavelier and Sieur de LaSalle traversed its waters in the 1600s. Prior to that, Native Americans inhabited the area; as you paddle today, you can spot a large hilltop monument which commemorates the Fox Wars.

Kayaking is a pretty popular activity in Chicago, though most people only think to explore the river within the city itself. The Chicago River is a wonderful option and takes a spot lower on this list, but kayaking Lake Michigan is truly a hidden gem. There are free-to-access launch points all along the lakeshore, making it obscenely easy to launch your own craft at a convenient spot. If you don’t have your own boat, you can rent one at North Avenue Beach. 

I stumbled onto this find on the 4th of July last summer. I found myself frustrated by the heavy crowds that flock to the lakeshore for the firework shows and sought an alternative. I envied the great view boaters had out on the lake, with hundreds of fireworks littering the lakefront and a perfectly situated front row seat to each one. And then it hit me. We grabbed our kayaks, donned a few safety lights, and set out just before sunset. 

We were rewarded with an evening we’ll never forget. There were more firework shows than we could count, with all of them shooting off over the lake — and we had the most covetable view in the city. While we were admittedly out on the best night of the year for firework viewing, Chicago’s Navy Pier fires off a show every Saturday and Wednesday night. After viewing them just once from the floating serenity of your kayak, you won’t want to watch them any other way. 

One of the greatest things about Chicago is that almost 100% of the waterfront is public access. So when summer (finally) comes around, I take full advantage of the beautiful beaches and sunny days. If you’ve got access to a kayak, your options don’t have to stop at the shoreline. Setting off along the coast is a great and unique way to experience the city, with stunning skyline views throughout and miles of coastline and beaches to explore.

If you’re looking to give this a shot, make sure to check the weather and water conditions beforehand. Lake Michigan isn’t your average lake, and its waves can reach some pretty gnarly heights. Make sure you’re prepared for whatever’s out there — make sure to have life vests and safety lights if you’re going for a night ride. Be aware of boaters at all times, particularly inebriated ones. Even if your craft technically has the right of way, be cautious, as some boaters aren’t paying attention; stay out of their path, stick to the shore, and avoid any potential disasters. 

Kayaking or canoeing the Wisconsin River is a true treat. The beautiful, open waters and scenic setting make this trip the picture of tranquility. The river is packed with idyllic sandbars seemingly designed for having a good time — you can picnic, camp, run around or lounge at a number of spots along the way. The river is famous for these sandbars, making it one of the most popular overnight kayak and canoe destinations in the region. And rightfully so. We ended up with an ideal spot about halfway through our route. On our private beach island, with its 360° views and pristine white sand beaches, we had found our own personal paradise.

Though we were there on a particularly slow day, the Wisconsin River typically has a fairly steady current which makes it an easy paddle. This is great for families, beginners or leisure trips. Combined with optimum camping conditions provided by the soft sand and wide open beaches, this spot will turn first-timers into life-timers. 

The only real downside to paddling the Wisconsin River is that, well, it’s in Wisconsin, making it a tricky day trip from Chicago. But with camping like this, it’d be a shame not to stay overnight anyway. Just like the Fox River paddle, there are more standard campgrounds at designated areas, but to pass up these beautiful, secluded sandbars to stay at a packed roadside campsite would be doing yourself a disservice. It’s hard to dream up more perfect conditions and if you’ve never camped off-site before, this is the trip to try it out.

The Skokie Lagoons are an interesting and easy to paddle network of twisting and turning channels, connecting together a set of seven lagoons on the Skokie River. The channels themselves are very narrow, which I personally prefer — something about paddling through low-hanging tree branches and shoelace streams makes the experience feel much more intimate, kind of like kayaking in Oregon. Having access to nature in such close proximity to the city makes the lagoons a great, convenient option for an afternoon trip that’s both kid and pet friendly.

It does take a bit of paddling to feel like you’ve truly left city life behind, though. When you first hit the water, you can still see and hear the busy traffic nearby. But if you explore deeper into the lagoon channels, thick with lush trees, greenery and wildlife, you’ll find those sounds start to fade away. It might not be a full disconnect from the chaos of the city, but it is still a great oasis and a healthy dose of nature’s medicine.

The fun of navigating through the dense and splintering pathways of the Skokie Lagoons is perfect for kids. The sense of adventure in discovering your route is a great way to foster kids’ love for outdoor exploration, and the overall simplicity of the network system makes it an easy and rewarding challenge for little ones. However, this leisurely and relaxing paddle might leave seasoned kayakers wanting more.

Chicago is known for its incredible architecture and the classic guided kayak tour is an awesome way to explore it. Having been on several tours throughout the city via busses, trolleys, and boats, I can say that there’s nothing like the view you get from gliding on the water. This city has enough history to fill a dozen tours, and every one I’ve been on has taught me fascinating facts about the city I call home. Even if you’ve already been on an architecture tour, don’t count out your chance to see the cityscape from the vantage point of a kayak. You’ll paddle past sights like the infamous “Corn Cob Towers” and the 4.2 million square foot Merchandise Mart — the largest commercial building in the world, (it even has its own zip code!).

A warm summer day is the perfect backdrop for this tour, but the lesser-looked-at sunset tours can offer stunning views of the city. On Saturdays, you can take a firework tour to catch the show at Navy Pier. If you’re not looking to stick with a guide and a tour group, there’s the option to rent kayaks from a few companies along the river. If you kayak this route, just stay alert. There’s lots of boat traffic along the river and it can get a bit chaotic on busy days; know the rules and follow them.

If you’re visiting Chicago and looking for an adventurous way to see it, this is the perfect option. You can soak in the towering architecture while floating down a lazy river flanked by wineries, restaurants, and gelato shops. Take note, this isn’t a city river known for its cleanliness, so you’ll definitely want to remain upright in your kayak, which shouldn’t be difficult as this is a tour most beginners will feel comfortable doing. Despite the less-than-stellar water quality, paddling the Chicago River is a wonderful way to explore a really beautiful city. Similar to what you can do while kayaking in Oregon on the Willamette River.