About this Experience
What you'll do:
You'll launch onto the Chicago River or Lake Michigan with a guide leading the way while your group paddles past some of the city's most recognizable skyline views from the water.
Guided kayaking experience: A professional guide handles the route, pacing, and safety instructions so your group can focus on enjoying the ride and the scenery.
Choose your route: Paddle through downtown on the Chicago Riverwalk or head onto Lake Michigan for wide-open skyline and waterfront views.
Beginner-friendly setup: A quick orientation and all required safety gear are included before launch, making the experience approachable even for total first-timers.
Single or tandem kayaks: Choose between solo paddling or sharing a kayak with someone in your group depending on your comfort level and vibe.
Unmatched city views: The perspective from the water puts Chicago's architecture, bridges, and skyline directly in front of you for the entire ride.
Most tours cover around 2.5 miles over roughly 90 minutes on the water, with a pace that works well for both casual paddlers and more active groups.
Why we love it for your group:
Easy active outing: It gets the group outside and moving without turning into a hardcore workout.
Chicago photo payoff: The skyline views from both the river and lakefront make this one of the best group-photo experiences in the city.
Private group energy: Your crew stays together throughout the tour, which keeps the experience social and relaxed.
Works across occasions: Bachelorette weekends, birthdays, reunions, and casual friend trips all fit naturally into this format.
Memorable without being complicated: Show up, paddle, laugh a little, and suddenly you have one of the highlights of the trip.
About this experience partner:
Urban Kayaks is a Chicago-based kayaking outfitter operating guided tours and rentals from both the Chicago Riverwalk and the Columbia Yacht Club lakefront location. Their team focuses on approachable, group-friendly experiences for visitors and locals alike, with guides who balance safety, city knowledge, and relaxed energy on the water. The company has become one of the city's most popular ways to experience Chicago's skyline beyond street level.
Additional information:
Tours typically last about 90 minutes.
Arrive at least 15 minutes early before launch time.
Single and tandem kayaks are available.
Tours may be rescheduled or refunded in cases of severe weather.
No prior kayaking experience is required.
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LocationChicago, IL
Chicago, IL 60601, USAChicago, IL
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Frequently Asked Questions
What do I need to be aware of before my tour?
- Please arrive 15 minutes before your scheduled tour time to use the washroom and stow items you don’t want to bring on the water. - If you are late to a scheduled tour, we can get you caught up as long as the group is still on land. Once the group is on the water, though, you will need to reschedule. - Plan on being on the water for approximately 90 minutes. - A normal tour travels about 2.5 miles along the Chicago River with frequent rest stops.
Are there any age restrictions?
- For all single kayak rentals that are unguided, you must be 18 years of age or older. - Teenagers 15-17 may paddle single kayaks in guided or supervised situations with parental consent. - Children under 15 must be accompanied by a parent or guardian in a tandem (two-person) kayak. - Toddlers ages 2-4 who weigh under 40 pounds must ride in a toddler seat between two adults. Toddler life vests are limited, so if you have one, bring it! Only very experienced paddlers can/should bring toddlers with them on the river. - All minors must have signed liability waivers and parental consent.
What is your policy if the weather is bad?
- The weather changes quickly in downtown Chicago, and it is often hard to predict what will happen in advance. We will make a call on whether tours are safe to continue at the time of your appointment. - In the event of severe weather, such as heavy rain and thunderstorms, we will cancel and offer a refund or option to reschedule. - If there is light rain or scattered showers, we often stay open. If we are open and you would like to cancel, you must do so at least 24 hours in advance of your tour or rental time to receive a refund. You always have the option to reschedule. - Our Lakefront location may close in the event of high winds on the lake.
