Paddle the Chicago River and learn downtown architecture in 3 hours
3 Hours
Guide, safety lesson, kayak
Kayak through downtown Chicago’s architectural canyons with guides who share stories of the city’s past, present, and future. Start with a lesson on paddle strokes, safety, and rules of the water before launching onto the river.
Children under 12 must ride with an adult on a double kayak; single kayaks are for ages 12+. Sea kayaks are only for guests with previous kayaking experience and equivalent rescue skills.
Cancel at least 48 hours before your tour or rental time to be refunded. Within 48 hours, you can reschedule for a $25/person rescheduling fee but will not be refunded.
You do not need kayaking experience. Some athletic ability is recommended, and you start with a lesson on paddle strokes, safety, and rules of the water.
Yes. Children under 12 must ride with an adult on a double kayak. Single kayaks are for ages 12+.
Sea kayaks are only for guests with previous kayaking experience who have completed the sea kayaking courses or have equivalent rescue skills. If you qualify and want a sea kayak, select a single kayak online and you will be sent out in a sea kayak.
1220 West Le Moyne Street Chicago, IL US 60642
Kayaking through downtown Chicago with this crew is genuinely hard to beat. Guides like Adam, Matt, and Antonio consistently earn praise for being knowledgeable, funny, and attentive, and the routes themselves are spectacular, whether you're paddling through calm wake-free zones around Goose Island or catching the river turn green on a seasonal tour. First-timers especially seem to feel well looked after, with solid instruction before hitting the water and staff who go out of their way to make sure everyone's comfortable. The experience itself is the star here. Calm water options make it approachable for beginners, while more adventurous paddlers can venture into the busier stretches of the Chicago River. A couple of negative reviews flag some concerning situations around safety response and customer service, so it's worth keeping that in mind. That said, those experiences appear to be outliers in an otherwise overwhelmingly positive track record. Overall, this is a well-run operation with genuinely passionate guides and a product that delivers a pretty unforgettable perspective on the city.
Fantastic experience and professional staff. Aaron was a terrific guide- very chill and friendly. He even had to tow a grown woman who registered and somehow didn’t realize paddling was involved in a 3 hour kayak tour (full disclosure: it is). Aaron then proceeded to tow her to the river bank after she somehow managed to flip out of her kayak (a feat that requires a lot of effort). I’ve kayaked many different times and places, including downtown Chicago on several occasions but never w Kayak Chicago or this far up the north branch of the river. I would definitely do it again and recommend to others- just be prepared to paddle.
Chris W
June 22, 2026
Fantastic experience and professional staff. Aaron was a terrific guide- very chill and friendly. He even had to tow a grown woman who registered and somehow didn’t realize paddling was involved in a 3 hour kayak tour (full disclosure: it is). Aaron then proceeded to tow her to the river bank after she somehow managed to flip out of her kayak (a feat that requires a lot of effort). I’ve kayaked many different times and places, including downtown Chicago on several occasions but never w Kayak Chicago or this far up the north branch of the river. I would definitely do it again and recommend to others- just be prepared to paddle.
Chris W
June 22, 2026
Cruise Chicago’s river in a vintage 1950s Milo Craft
Pilot a 2-person Craig Cat and cruise the Chicago River skyline
Cruise the Chicago River for 2 hours on a private, self-drive pontoon
Paddle the Chicago River after dark with city lights and stories from your guide
Paddle Lake Michigan’s shoreline for city views and guided instruction
Night kayak tour to watch Navy Pier fireworks
Paddle the Chicago River past the Wild Mile and downtown skyline
Choose your paddlecraft for a self-guided outing on the water
Paddle past the Wild Mile and Chicago's skyline in a single or double kayak