What you'll do:

Hit the water and see Chicago from a whole new angle with a private group kayaking experience along the Riverwalk or Lake Michigan lakefront. Whether you're paddling past iconic skyline views or cruising calm waters with your crew, this is the perfect mix of adventure, chill vibes, and unforgettable scenery. With expert guides leading the way, you’ll get set up with everything you need before heading out for a fun, active experience that’s just as great for first-timers as it is for seasoned paddlers. Expect laughs, team bonding, and plenty of photo-worthy moments along the way.

Why we love it for your party:

• A unique, active experience that gets everyone off their phones and on the water

• Unreal skyline views you won’t get anywhere else (hello, Insta moments)

• Great for any group vibe—birthdays, bach parties, friend trips, or reunions

• Private group options make it feel exclusive and customizable

• Equal parts fun and relaxing—paddle hard or just cruise and vibe

About this experience partner:

Founded by a team of Chicago locals, Urban Kayaks gives visitors the chance to experience the Windy City from the water. As native Chicagoans and avid adventurers, our goal is to showcase our hometown in a fun and unique way. While kayaking, guests can interact with our knowledgeable and courteous staff members and even say ‘hi’ to the office’s resident pooches. We absolutely love Chicago and can’t wait to share more about us, the city that raised us.

Additional information:

• Starting at $35 per person (pricing varies by location and group details)

• Locations:

  • Riverwalk (Primary location): 435 E Riverwalk, Chicago, IL 60601

  • Lakefront: Columbia Yacht Club - 111 N. Lake Shore Dr, Chicago, IL 60601

• Options for single and tandem kayaks

• Guided experiences led by professional instructors

• Safety equipment and basic instruction included

• Suitable for beginners and all skill levels