Kayaking in Winnetka, IL


One or Two Full-Day Kayak Rentals with Beginner Land-Based Lessons from Kayak Morris (Up to 52% Off)

Kayak Morris

Morris

On-land lesson covers safety and essential strokes before students pilot craft on a nearby beginner waterway for the rest of the day

$80 $39

Two-Hour Kayaking for One or Two from Lake Katherine Nature Ctr/Botanic Garden (Up to 31% Off)

Lake Katherine Nature Ctr/Botanic Garden

Palos Heights

Guests rent kayaks for paddling past beavers, herons, and turtles of Lake Katherine, with walks through scenic botanical gardens afterwards

$16 $12

Architecture and History Kayak Tour or Shady Chicago Kayak Tour for Two or Four from Wateriders (Up to 42% Off)

Wateriders Kayak Tours

Riverwalk

Guides spin true tales of Windy City history and architecture; the gritty underbelly takes center stage in the Ghosts and Gangsters tour

$130 $78

Kayaking Class for One, Two, or Four with Naperville Kayak (Up to 51% Off)

Naperville Kayak

Naperville Kayak

Float on the waters of downtown Naperville’s Paddleboat Quarry in a kayak, and learn basic kayaking techniques

$59 $35

Full-Day SUP or Kayak Rental at Mill Race Cyclery (50% Off). Four Options Available.

Mill Race Cyclery

Geneva

Renters can choose to cruise the Fox River atop a stable standup paddleboard or sitting on a single-person or tandem kayak

$50 $30

City Lights Night Paddle

Kayak Chicago - Chicago River

Goose Island

$64.31 $38.91

Architectural Kayak Tour

Kayak Chicago - Chicago River

Goose Island

$75.21 $45.11

Sunset Paddle

Kayak Chicago - Chicago River

Goose Island

$64.31 $38.91

Climbing, Kayaking, Ziplining, or Outdoor-Adventure Combo for Two from Vertical Adventure Guides (50% Off)

Vertical Adventure Guides

Multiple Locations

Experienced guides lead participants on outdoor adventures, from top-rope rock climbing to kayaking to ziplining up to 20 ft. off the ground

$150 $75

Lake Paddle

Kayak Chicago - North Avenue Beach

North Side

$75.21 $45.11

Electric- or Pontoon-Boat Rental for Up to 12 from Vantage Boat Share (Up to 50% Off)

Vantage Boat Share

River North Marina on the Riverwalk

Passengers cruise the Chicago River on a luxury pontoon or electric boat

$200 $99

Pontoon-Boat Rental for 8 or 12 from Corporate Tailgate Boat Rental (Up to 56% Off). Three Options Available.

Corporate Tailgate Boat Rentals-Chicago

Chicago

Pontoon boats cruise leisurely up and down the Chicago River on a waterfront tour; see Navy Pier fireworks; bring your own food and drinks

$300 $139

Petting Farm and Animal Park Admission for Two, Four, or Six to Jo-Don Farms (40% Off)

Jo-Don Farms

Caledonia

Guests greet more than 200 animals, from camels to tigers, at zoo open for 40 years

$10 $6

"Learning The Ropes" or "Learning To Boulder" Classes for One or Two at First Ascent Climbing (Up to 49% Off)

First Ascent Climbing

Multiple Locations

Learn rope skills for climbing up to 6 stories tall, or learn technique for bouldering, a more powerful style of climbing on shorter walls.

$73 $39

Scuba-Diving Course with Option for Certification at Berry Dive Center (Up to 75% Off). Four Options Available.

Berry Dive Center

Northbrook/Glenview

Scuba instructors lead students in diving techniques during weekend lessons inside classrooms, pools, and open water

$75 $19

$29 for a Hobie Eclipse and Paddleboard Rental Package from Chicago Water Sport Rentals ($54.95 Value)

Chicago Water Sport Rentals

Online Deal

Glide across the water with a simple pedaling motion on a Hobie Eclipse standup pedal-board, and further explore the waters on a paddleboard

$54.95 $29

Intro to Climbing Class, Day Passes for Two, or Family Pass at Upper Limits Rock Climbing Gym (Up to 59% Off)

Upper Limits Rock Climbing Gym

Bloomington

Climbers of all experience levels learn to scale the rocks in this 20,000-square-foot climbing gym

$30 $15

Daytime or Sunset Cruise with Drinks from Tall Ship Red Witch (Up to 31% Off)

Tall Ship Red Witch

Kenosha Harbor

Passengers relax on Kenosha’s only wooden tall ship while enjoying three drinks; Readers’ Choice award winner

$37 $26

$269 for Scuba Certification Course with Equipment Rental, Materials, and Gear Credit ($500 Value)

Got Air Scuba

Elk Grove Village

PADI instructors let students try out equipment or lead classroom, pool, and open-water instruction for open-water certification

$500 $269

BYOB Lazy-River Tubing Trip for One or Two from Larsen's Landing Outfitters (Up to 40% Off)

Larsen's Landing Outfitters

Woodfield Mall

BYOB lazy-river tubing trips on the Kishwaukee River include round-trip transportation, tube rentals, and an all-you-can-eat taco bar

$125 $79

Two-Hour Sailing Charter for Up to Six from Come Sailing (Up to 70% Off). Three Options Available.

Come Sailing

Chicago

Captain and full crew take groups of up to six people out onto Lake Michigan, where they can see breathtaking views of the shore and skyline

$350 $105

$15 For $30 Toward Your Choice Of Sporting Goods

KIRHOFER'S SPORTS

Blackberry Countryside

$30 $15

Weekend or Weekday BYOB Sailing Charter at Millennium Sailing (Up to 50% Off)

Millennium Sailing

Millennium Sailing

Take in stunning skyline views while sailing on Lake Michigan during a two-hour BYOB chartered voyage

$360 $179

$130 for a Computer Nitrox Diver Scuba Diving Course with Online Materials and Certification Card at Dive Right In Scuba ($250 Value)

Dive Right In Scuba

Plainfield

Open Water Diver certification holders learn to dive using Nitrox as a breathing gas to reduce post-dive fatigue and increase safety margins

$250 $130

Two-Hour Private Cruise for Up to 6 from New Buffalo Sailing Excursions (Up to 44%Off). Four Options Available.

New Buffalo Sailing Excursions

New Buffalo

Groups climb aboard a 31-foot sailboat to enjoy a 2-hour cruise during the day, sunset or at night; BYOB friendly

$300 $173

Discover Scuba Class at Chicagoland Scuba (58% Off)

Chicagoland Scuba

Lake Zurich

Discover Scuba offers a brief introduction of all the ins and outs of underwater excursions

$60 $25

Private BYOB Sailboat Cruise for Up to Six People from The Salty Dog Sailing Co. (Up to 50% Off)

The Salty Dog Sailing Co.

Burnham Harbor

At Burnham Harbor, board a 34-foot yacht for a nautical adventure on Lake Michigan complete with BYO food and drinks and skyline views

$550 $275

Two- or Three-Hour Boat Rental for Up to Six from Chicago Adventure Club (Up to 39% Off)

Chicago Adventure Club

Burnham Harbors

Groups of up to six cruise the waters of Lake Michigan in a sleek Carver 350 Mariner yacht during two- or three-hour rentals

$740 $499

Up to 50% Off watersport rental at Apex Luxury Rental LLC

Apex Luxury Rental LLC

Far South Chicago

From the merchant: UNLIMITED Monthly Memberships, UNLIMITED Daily Wrist Bands & Tours for Half-Price Invest Today & begin your excursion

$230 $135

Rowing Machine, Scull Rowing, or Both Lessons for Up to Three People at Northshore Fitness Studio (Up to 60% Off)

Northshore Fitness Studio

Multiple Locations

Rowing Machine class works upper-body strength on indoor ergometers; Scull Rowing teaches fundamental moves

$75 $30

Select Local Merchants

  • The Northwest Passage Chicago
    Founder Rick Sweitzer started the adventure travel company in 1983 before leading one of the first amateur dogsled expeditions to North Pole. Driven by his vision, the guides and instructors of The Northwest Passage lead travelers of all skill and fitness levels to some of the most dramatic terrain on the planet. Locally, the team leads outings around the Chicago area, ranging from stand-up paddleboarding classes on Lake Michigan to kayaking and camping trips in Door County, Wisconsin. As for the rest of the world, Northwest Passage sends it adventurers to conquer it locale by stunning locale during programs that include hiking across Europe, trekking to remote Polar regions, and dressing up like scientists to infiltrate Area 51.
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    Wilmette, IL US
    +18479204409
  • Northwestern University Baseball Camps
    Evanston's Northwestern University Baseball Camps is a great place to stop in for some fun. Parking is plentiful, so guests can feel free to bring their vehicles. Northwestern University Baseball Camps is a place you'll love to visit, so don't wait around, give them a call today!
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    Evanston, IL US
  • Laserperformance Hedlund Marine Sports
    Take a nautical adventure around Evanston when you rent a vessel from Laserperformance Hedlund Marine Sports. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    Evanston, IL US
    +18478667765
  • SideTour - Leisure
    There's really no better place to spend the weekend with your family than at SideTour - Leisure in Highland. You may want to pack a change of clothes before heading to SideTour - Leisure, where students rave about the hot yoga classes. Take advantage of one of these aerial yoga classes and experience the thrill of flying and suspension. Enter into combat (paintball combat, that is) at SideTour - Leisure, and get ready to pull out the big guns. Parking is plentiful, so patrons can feel free to bring their vehicles. So head to SideTour - Leisure for some fun, laughs, and a great experience.
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    Highland, IL US
  • Midwest Paddlesport Adventures
    With an armada of kayaks, canoes, and stand-up paddleboards at their command, Midwest Paddlesport Adventures' team spearheads expeditions to bodies of water across Northern Illinois and Southern Wisconsin. Frequent trips include calming floats down the Fox River––which is densely populated by local wildlife––and Lake Andrea, a former quarry characterized by local rocks. The expert navigators safely guide groups to their destinations, pointing out animal tracks and majestic waterfowl and they commute to the office.
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    Rolling Meadows, IL US
    +18477674244
  • Urban Kayaks - Chinatown
    Brothers Aaron and Asher Gershenzon and friend James Morro grew up in the city but always possessed a passion for the outdoors. They practiced wilderness kayaking for most of their lives before earning their American Canoe Association certifications on Lake Superior. Each of them brings dual passions for their home city and outdoor sports to the company’s guided group and private kayak trips. Every paddle outing is different as guides blend downtown architectural commentary and little-known gangster stories with tie-ins to current events. Though each guide tells different stories, often interspersed with humor, all of them focus on environmentally friendliness. Paddling trips utilize a fleet of lime-green Confluence Watersports kayaks, and staffers often wear lime-green shirts—all of which render them easily identifiable from the Riverwalk but well-camouflaged in supermarket produce sections. Up to four guides lead groups of 15 or fewer kayakers, first preparing them with a briefing on paddling techniques, rules of the river, and assurances of the stability of their wide recreation kayaks. The guides' watchful eyes and constant advice have instilled confidence in even the most unsure participants. When not guiding trips, staffers extend their easygoing atmosphere to their office—nestled across the river from the Centennial Fountain's Water Arc—where the storefront lies amid the bustling city that surrounds it. Inside the shop, the owners' much-beloved pooches frolic around a hanging hammock.
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    Chicago, IL US
    +13129650035

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