Chicago is famous for many things—astonishing skyscrapers, Art Deco architecture, the blues, Al Capone, Michael Jordan and the Bulls, Navy Pier—but kayaking isn’t generally one of them.
Ask a local about must-have Chicago experiences, however, and they might recommend a sunset tour up the city’s central artery, the Chicago River; or an afternoon in the surf when the wind is blowing over Lake Michigan.
Heading up the Chicago River from the lake, paddlers are immediately engulfed by the city. A chasm of glass and limestone towers a thousand feet above the river—it’s a landscape every bit as dramatic and improbable as the Grand Canyon.
“This is the paddle we do when people come to visit,” confirm Chicago locals Alec and Sharon Bloyd-Peshkin, founders of Have Kayaks Will Travel. “It’s just spectacular, especially in the fall or in the evening with the sun setting behind the city.”
The Best Places to go kayaking In Chicago
For a guided kayak trip
Kayak Chicago
For a memorable, half-day kayaking or paddleboard tour, join Kayak Chicago. From their location just off North Avenue, tours lead through what they call the “Wild Mile” around Goose Island before leading into the canyon of the city skyline. Kayak Chicago also has evening tours under the city lights for an unforgettable way to experience the city on a spring or summer night.
Have Kayaks Will Travel
Have Kayaks Will Travel offers informative, small-group tours, including a Devil in the White City trip based on the Erik Larson page-turner. “We paddle kayaks or canoes in the area the book is set in, on Chicago’s south side,” says Sharon, “exploring what happened here during the 1893 World’s Fair.”
Urban Kayaks
Founded by two brothers, Urban Kayaks provides kayak tours and rentals at two locations: the Riverwalk on the Chicago River and at the Monroe Harbor on the Lake Michigan lakefront. The Riverwalk location launches kayakers in a spot instantly surrounded beneath the city’s stunning skyscrapers. The Monroe Harbor offers a lakefront launch for kayak and paddleboard tours and rentals with expansive 360-degree views of the skyline and Lake Michigan.
Wateriders
Since 1997, Wateriders has been leading kayaking tours of Chicago. Their East Bank location puts paddlers near Wolf Point and the confluence of the three branches of the Chicago River for a most impressive view of the city. They also have some fascinating kayak tours including history and architecture, and ghost and gangster paddles. For those seeking the under appreciated natural side of Chicago, Wateriders Bridgeport tour offers a contrast to skyscrapers, where you’ll glide past blue heron and painted turtles.
To paddle the Chicago River like a local
“Put-in on the Chicago River just west of Chinatown and head north, turning east on the Main Branch right through the heart of the city,” says Sharon.
She suggests launching from the dock at kayaker-friendly Lawrence’s Fisheries and making the four-mile trip to the lock at the river mouth. Fried seafood fans can follow up with a plate (or paper bag) of Lawrence’s famously crispy fish and shrimp.
To kayak and dine
Start as above from Lawrence’s Fisheries on the Chicago River, but proceed through the lock when you reach the lake. Paddle out to the end of Navy Pier, admiring its century-old amusement park, Crystal Gardens and phenomenal skyline views. Head south on Lake Michigan alongside the city’s world-renowned waterfront park system. Landing is permitted at select beaches during summer; pull ashore at 12th Street Beach (eight miles one-way) and grab a bite at tasty Del Campo Tacos.
If you’re Craving waves on Lake Michigan
“Look at Google Maps and you’ll see why Montrose Beach gets the most amazing reflective waves,” says Alec. He also recommends Rainbow Beach for excellent surfing when the wind is north or east, with maximum fetch out of the northeast. “Both of these beaches have a fishhook shape that catches the northeast waves really well.” Launch at the north end of Montrose, by Wilson Park.
Kayak Rentals in Chicago
Many of these tour operators and even city parks also provide kayak rentals and a convenient launch site to get you on the water around Chicago without a guide or boat of your own.
Paddling the Chicago River Water Trail Safely
The Chicago River provides one of the most incredible urban waterscapes for kayaking and paddleboarding in the U.S. However, kayakers, paddleboarders and other recreational users need to be aware the river corridor, especially at the city center, is an active waterway they will be sharing with motorized traffic.
The city has a free online guide to help safe recreation on the river. The guide provides an understanding of the traffic levels paddlers can expect and guidance to have a safe experience. The info page also includes a link to a Chicago River Water Trail Map, which includes access points throughout the city for both human-powered and motorized watercraft.
Considering the weather when paddling in the city
It isn’t called the “Windy City” for nothing. Whenever you are planning to paddle in Chicago, you want to know what conditions will look like throughout the course of your outing. This means wind, and even the waves it can produce in exposed water like Lake Michigan. You should also check water and air temperatures to dress for kayaking accordingly.
Lightning storms are another factor to take into account in the late spring and summer months when conditions can change rapidly and lightning poses a danger to anyone on the water. Be sure to check not only the current weather and water conditions, but what the forecast looks like in the hours ahead when you plan to enjoy your trip.
Feature Photo: Joshua Mellin
