Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Chicago…
    3. /Water Activities
    4. /Kayaking Tours
    5. /Chicago River 2-Hour Kayak Rental
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Gallery image

    Chicago River 2-Hour Kayak Rental

    Paddle Chicago River routes in a single or double kayak

    4.7 stars• 487 reviews

    Duration

    2 hours

    Includes

    Single or double kayak rental

    Highlights

    Explore the Chicago River by kayak, from the Wild Mile to downtown's glass-and-steel river canyons. Choose a single kayak for solo paddling or share a double kayak with a partner.

    • Explore Goose Island and the Wild Mile
    • Paddle toward Wolf Point, Lake Shore Drive, the South Loop, or Chinatown
    • Look for ducks, turtles, beaver, and birds along the river
    • Navigate downtown beneath historic bridges and alongside city architecture
    • Enjoy recreational kayaks suitable for all experience levels

    Important details

    • Arrive 15 minutes early for orientation and safety instructions
    • Complete the waiver before you arrive
    • Children under 12 must ride with an adult in a double kayak
    • Sea kayaks require previous kayaking experience and completed sea kayaking courses or equivalent rescue skills
    • A credit card remains on file for added rental time and lost, missing, or damaged equipment
    • A credit card processing fee applies and is not included in the listed price
    • Added rental time is charged at hourly rates, with charges stopping after the first 3 hours
    • Return by closing time: 7 p.m. in summer or 6 p.m. in September

    Cancellation Policy

    Cancel at least 48 hours before your scheduled time for a refund. Within 48 hours, you can reschedule for a $25 per person fee but won't receive a refund.

    Product ID: QEXEMG

    FAQs

    Check out in the office with staff when you return so they know you are off the water.

    Meeting details

    1220 West Le Moyne Street, Chicago, IL 60642

    Experience provided by Kayak Chicago

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Single Kayak

    from $86.93

    Seats 1 Person

    0

    Double Kayak

    from $111.76

    Seats 2 People

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.7
    Excellent
    487 reviews•Google Maps
    389
    42
    11
    7
    15

    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.

    What people are saying

    Review 1 of 5
    5/5

    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!

    Photo of Rebeca Lisboa

    Rebeca Lisboa

    August 30, 2026

    Review 1 of 1
    5/5

    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!

    Photo of Rebeca Lisboa

    Rebeca Lisboa

    August 30, 2026

    Great for groups

    1950s Boat Rental on Chicago River
    Boat RentalsUp to 6

    1950s Boat Rental on Chicago River

    Cruise Chicago’s river in a vintage 1950s Milo Craft

    Cruise Chicago’s river in a vintage 1950s Milo Craft
    4.7 • 487 reviews
    $559/ boat
    Explore the Chicago River on a 2-Hour E-Boat Rental
    Boat Rentals2

    Explore the Chicago River on a 2-Hour E-Boat Rental

    Pilot a 2-person Craig Cat and cruise the Chicago River skyline

    Pilot a 2-person Craig Cat and cruise the Chicago River skyline
    4.7 • 487 reviews
    $211
    Drive an 18' Pontoon on the Chicago River
    Boat RentalsUp to 6

    Drive an 18' Pontoon on the Chicago River

    Cruise the Chicago River for 2 hours on a private, self-drive pontoon

    Cruise the Chicago River for 2 hours on a private, self-drive pontoon
    4.6 • 122 reviews
    $173

    Nearby activities

    Chicago Night Kayak Tour
    Kayaking Tours

    Chicago Night Kayak Tour

    Paddle the Chicago River after dark with city lights and stories from your guide

    Paddle the Chicago River after dark with city lights and stories from your guide
    4.7 • 487 reviews
    $82/ kayak
    3-Hour Chicago River Architectural Kayaking Tour
    Kayaking Tours

    3-Hour Chicago River Architectural Kayaking Tour

    Paddle the Chicago River and learn downtown architecture in 3 hours

    Paddle the Chicago River and learn downtown architecture in 3 hours
    4.7 • 487 reviews
    $82/ kayak
    Chicago River 1-Hour Kayak Rental
    Kayaking Tours

    Chicago River 1-Hour Kayak Rental

    Paddle the Chicago River past the Wild Mile and downtown skyline

    Paddle the Chicago River past the Wild Mile and downtown skyline
    4.7 • 487 reviews
    $43/ kayak
    Chicago River 2-Hour Kayak & Paddleboard Rental
    Kayaking Tours

    Chicago River 2-Hour Kayak & Paddleboard Rental

    Choose your paddlecraft for a self-guided outing on the water

    Choose your paddlecraft for a self-guided outing on the water
    4.7 • 487 reviews
    $87/ kayak
    Chicago River 2-Hour Kayak Rental
    Kayaking Tours

    Chicago River 2-Hour Kayak Rental

    Paddle past the Wild Mile and Chicago's skyline in a single or double kayak

    Paddle past the Wild Mile and Chicago's skyline in a single or double kayak
    4.7 • 487 reviews
    $87/ kayak
    Chicago River 1-Hour Kayak & SUP Rental
    Kayaking Tours

    Chicago River 1-Hour Kayak & SUP Rental

    Explore Chicago River routes by kayak or stand-up paddleboard at your own pace

    Explore Chicago River routes by kayak or stand-up paddleboard at your own pace
    4.7 • 487 reviews
    $43& up