We Found These Experiences For You (24)
1 Hour Kayak Rentals: Chicago River
All Ages & Skills • Single & Double Kayaks • Save $2 each by booking online!
Reserve online & Save $2 each! Single and double kayak rentals on the Chicago River. Chicago’s original kayak and paddleboard outfitter. Our kayak shops have everything you need for your urban adventure. Enjoy a single kayak on your own, or share the experience with a partner in a double kayak! ...
Chicago
1 Hour with the option to extend
Kayak
Kayak Chicago
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2 Hour Kayak Rental: Chicago River
Most popular! • All Ages & Skills • Single & Double Kayaks • Save $2 each by booking online!
Reserve online & Save $2 each! Single and double kayak rentals on the Chicago River. Chicago’s original kayak and paddleboard outfitter. Our kayak shops have everything you need for your urban adventure. Enjoy a single kayak on your own, or share the experience with a partner in a double kayak! ...
Chicago
2 Hours
Kayak
Kayak Chicago
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E-Boat Rental
Ages 21+ to rent • Ages 16+ w/ License to operate • Seats 2 People
Reserve online & Save The Craig Cat is a high-performance compact power catamaran designed for fishing, cruising, and, leisure, often described as a hybrid between a boat, jet ski, and go-kart More info You must check out in the office with our staff when you return, so we know you are off the water
Chicago
2 Hours
Boat Rental
Kayak Chicago
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Classic 1950's Milo Boat Rental
2 hours • Up to 6 people • Reserve in advance!
Reserve online & Save 1950s Milo Craft. a charming and elegant cruiser. Explore the Chicago River with stunning skyline views See historic bridges, architecture, and hidden river sections expert staff More info You must check out in the office with our staff when you return, so we know you are off ...
Chicago
2 Hours
Boat Rental
Kayak Chicago
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Architectural Tour
Most Popular • 3 Hours • All Ages • Online discount
Reserve online & Save $2 each! Paddle the architectural canyons of the Chicago River on our architectural tour! Join us as we embark on a voyage of history and architecture through downtown Chicago. Your tour begins with a lesson in paddle strokes, safety, and rules of the water. In addition, after ...
Chicago
3 Hours
Boat Tour, Kayak
Kayak Chicago
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City Lights Night Paddle
All Ages • 3 Hours • Online discount
Reserve online & Save $2 each! The city lights are gorgeous at night, and the Spring and Summer weather is perfect for an evening paddle. We will start at dark and paddle down the Chicago River to enjoy the city lights reflecting in the river and off the buildings. With lights on your boat we will ...
Chicago
3 Hours
Boat Tour, Kayak
Kayak Chicago
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Fireworks Tour
All Ages • 3 Hours • Online discount
Reserve online & Save $2 each! Paddle through the city at night to watch the Fireworks Spectacular at Navy Pier, which takes place from Memorial Day through Labor Day. Their fireworks display is a great show for you and your friends, especially on a kayak. Gift certificates are available if you would ...
Chicago
3 Hours
Boat Rental, Gift Card, Kayak
Kayak Chicago
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Sunset on the Chicago River
All Ages • 3 Hours • Online discount
Reserve online & Save $2 each! Enjoy the sunset on the Chicago River. See the sunset as it reflects off of the towers of glass and steel and onto the water beneath you. Your evening begins with an orientation to kayaking. You will begin the evening by meeting your guides near the North Branch of ...
Chicago
3 Hours
Boat Tour, Kayak
Kayak Chicago
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St. Paddy’s Day Green River Tour
All Ages • 3 Hours • Online discount
Reserve online & Save $2 each! Come join us for St. Paddy’s day as we paddle the emerald water for the annual dying of the Chicago River! Be one of the few to experience the green water as thousands of on-lookers crowd the bridges and river banks. Paddle a single or double kayak or embark in our ...
Chicago
3 Hours
Boat Tour, Kayak
Kayak Chicago
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Learn to Kayak
All experience levels welcome • 2 Hours
Learn to Kayak A great class for beginners looking for the basic techniques to get out and enjoy flat calm water. You will learn the different types and styles of boats, how to outfit your kayak, safety procedures, rules of the water, boat control, balance and basic paddling techniques skills. Class ...
Chicago
2 Hours
Kayak
Kayak Chicago
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1 Hour Kayak & SUP Rentals: Montrose Beach
All Ages & Skills • Single Double Kayaks & SUPs • Save $2 each by booking online!
Reserve online & Save $2 each! Single and double kayak rentals on the Chicago River. Chicago’s original kayak and paddleboard outfitter. Our kayak shops have everything you need for your urban adventure. Enjoy a single kayak on your own, or share the experience with a partner in a double kayak! ...
Chicago
1 Hour with the option to extend
Kayak
Kayak Chicago
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2 Hour Kayak & SUP Rentals: Montrose Beach
All Ages & Skills • Single & Double Kayaks • Save $2 each by booking online!
Reserve online & Save $2 each! Single and double kayak rentals on the Chicago River. Chicago’s original kayak and paddleboard outfitter. Our kayak shops have everything you need for your urban adventure. Enjoy a single kayak on your own, or share the experience with a partner in a double kayak! ...
Chicago
2 Hours
Kayak
Kayak Chicago
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Air and Water Show Tour
2 Days Only: 2026 August 15-16 • 4 hours • All Ages • Online discount!
Two days only. Reserve online & Save $2 each! Join us on the water during the air and water show for the best seat in the house! The tour begins at Montrose beach with an orientation, teaching paddle strokes, safety and rules of the water. Once on the water, we will paddle towards North Ave. Beach ...
Chicago
4 Hours
Kayak
Kayak Chicago
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Intro to Sea Kayaking
All experience levels welcome • 4 Hours
Sea Kayaking In this 4-hr. Introduction to sea kayaking course, you will learn kayak nomenclature, paddling techniques, rescues and everything you need to be safe and feel comfortable on the water. We will teach the basics of paddle stroke techniques, wet-exits, cowboy rescues, partner assisted T-rescues, ...
Chicago
4 Hours
Kayak
Kayak Chicago
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Intermediate Kayaking
Must have previous kayaking experience or completed our Introduction to Kayaking course • 4 Hours
Intermediate Kayaking Ready for the next level in your sea kayaking training? Our intermediate sea kayaking class will thoroughly advance your paddling skills and confidence on open water. Our certified instructor will cover: Hip snap development (controlling your boat with your body) Self rescues (paddle ...
Chicago
4 Hours
Kayak
Kayak Chicago
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Intro to Stand-Up Paddleboard
All experience levels welcome • 2 Hours
Intro to Stand-Up Paddleboard This Intro to SUP course is designed to provide you with the skills and knowledge to enjoy the sport of standup paddle boarding (SUP). You will learn board parts and types, how to easily stand up, balance and board control, paddling techniques, turning and controlling your ...
Chicago
2 Hours
SUP
Kayak Chicago
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1 Hour Kayak Rentals: North Avenue Beach
All Ages & Skills • Single & Double Kayaks • Save $2 each by booking online!
Reserve online & Save $2 each! Single and double kayak rentals on the Chicago River. Chicago’s original kayak and paddleboard outfitter. Our kayak shops have everything you need for your urban adventure. Enjoy a single kayak on your own, or share the experience with a partner in a double kayak! ...
Chicago
1 Hour with the option to extend
Kayak
Kayak Chicago
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2 Hour Kayak Rental: North Avenue Beach
All Ages & Skills • Single & Double Kayaks • Save $2 each online!
Reserve online & Save $2 each! Single and double kayak rentals on the Chicago River. Chicago’s original kayak and paddleboard outfitter. Our kayak shops have everything you need for your urban adventure. Enjoy a single kayak on your own, or share the experience with a partner in a double kayak! ...
Chicago
2 Hours
Kayak
Kayak Chicago
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Lake Shore Skyline Paddle
All Ages & Skills • 2.5 hours • Save $2 each online!
Your skyline paddle tour begins with an orientation to paddling. You will learn basic paddle strokes, safety, and rules of the water. Once on the water, our guides will lead you along the shoreline for an incredible view of the city. Together we'll paddle past beaches & breakwalls truly experiencing ...
Chicago
2.5 Hours
Boat Tour, Kayak
Kayak Chicago
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VIP Season Passes
Every tour, rental, lesson is free
Looking for great deals? The VIP is the all inclusive season pass that gives you total access to all of our instructional classes, guided tours and rentals. Accordingly, you can learn and expand your techniques with instructional classes, take each class as many times as you like. Also, you can join ...
Viewing 1 to 20 of 24 Experiences