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DC Kayaking » A tourist guide to Chicago kayak rentals

A tourist guide to Chicago kayak rentals

A Chicago kayaking flag

CHICAGO — When I learned I would be headed here for a mid-October conference, I investigated whether I could rent a kayak. I found several options though given the time of year, the weather would be a big factor, just as it is in Washington, D.C.

Thankfully, the day I arrived, Sunday, October 16 the weather was just good enough for rental availability. I rented from two separate vendors.

Kayak Chicago

My first destination was Kayak Chicago on Goose Island. I rented a bicycle at Navy Pier and biked up. Kayak Chicago wasn’t busy on the overcast, windy day. I was welcomed warmly by staff and had the most thorough instruction from a kayak vendor to date. 

I paddled the North Chicago River around Goose Island in a clockwise direction. The skyline loomed in the distance with the Willis (nee Sears) Tower in the distance straight. The John Hancock building was off to my left. In the foreground, drawbridges, new big box development, old industry, a few docks and trees in their autumn glory. 

All told, it took me about 40 minutes to circumnavigate the island. I was told 45 to 60 minutes was more typical.

Kayak Chicago offers tours and covers more than just the Goose Island loop. If I get back again, I’d be inclined to head down to the confluence of the two branches of the river.

The conditions are suitable for entry level kayakers.

Urban Kayak 

Next, I headed downstream for the Riverwalk in the Loop. There I rented from Urban Kayaks . They are right on the south side of the river not far from Lake Shore Drive. A 5½ minutes long safety video with a “talking dog” was required before heading out. 

Paddling on the Chicago River is a much different experience. Visually, both sides are lined with Riverwalk and skyscrapers. The water itself is much busier with countless tour boats pulling in and out. Kayakers are instructed to keep close to the sides and yield to other water traffic. The boats create wakes, so it’s not flat water like upriver. It’s a blast though, between the swells and the scenery. I paddled between the Lake Shore Drive bridge and where the river forks. If I had more time on my bike rental, I’d have explored the forks more.

I recommend intermediate-level kayakers and above inside the Loop.

Urban Kayaks also has a Lake Front location, but that was closed for the season.


There are a few other kayak rental options in Chicago in-season:

Chicago River Canoe & Kayak | Wateriders