Learn essential sea kayaking skills with certified instructors
4 hrs
Classroom, beach & on-water
Build foundational sea kayaking skills with certified instructors. Practice essential techniques in classroom, beach, and on-water sessions.
Cancel at least 48 hours before your scheduled time for a refund. Cancellations within 48 hours can be rescheduled for a $25 per-person fee but are not refundable.
Product ID: 5WQAH3
200 West Montrose Harbor Drive, Chicago, IL 60640
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.
Amazing experience! Great people and great instructor, very patient, friendly and funny! Totally recommend it! Chicago at night is magical! Definitely the highlight of my trip!
Rebeca Lisboa
August 30, 2026
Amazing experience! Great people and great instructor, very patient, friendly and funny! Totally recommend it! Chicago at night is magical! Definitely the highlight of my trip!
Rebeca Lisboa
August 30, 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 the Chicago River and learn downtown architecture in 3 hours
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
Explore Chicago River routes by kayak or stand-up paddleboard at your own pace