Sailing in Des Plaines


Tall Ship Red Witch: Sail Aboard Tall Wooden Ship Red Witch in Chicago (Up to 52% Off)

Sail Aboard Tall Wooden Ship Red Witch in Chicago (Up to 52% Off)

Tall Ship Red Witch

Burnham Harbor - J Dock

Passengers relax on Chicago’s only wooden tall ship while viewing the skyline or fireworks; Readers’ Choice award winner

$60 $29

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The Salty Dog Sailing Co.: 2.5-Hour Private BYOB Cruise on a Sailboat for Up to Six People from The Salty Dog Sailing Co. (Up to 49% Off)

2.5-Hour Private BYOB Cruise on a Sailboat for Up to Six People from The Salty Dog Sailing Co. (Up to 49% 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

$490 $249

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Offshore Adventures Chicago: Two-Hour BYOB Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 70% Off)

Two-Hour BYOB Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 70% Off)

Offshore Adventures Chicago

The Loop

Daytime or sunset Lake Michigan cruises delight with views of the Chicago skyline; passengers can bring their own drinks and playlists

$220 $69

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Millennium Sailing: Up to 50% Off BYOB Sailing Charter at Millennium Sailing

Up to 50% Off BYOB Sailing Charter at Millennium Sailing

Millennium Sailing

Central Chicago

From the merchant: Experience the sport of sailing while enjoying the skyline from the lake, or just hang out at the Play Pen.

$400 $199

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3rd Coast Cruising: One or Two Three-Hour Introductory Sailing or Racing Lessons from 3rd Coast Cruising (Up to 68% Off)

One or Two Three-Hour Introductory Sailing or Racing Lessons from 3rd Coast Cruising (Up to 68% Off)

3rd Coast Cruising

DuSable Harbor

US Coast Guard–certified captains and certified instructors welcome sailors aboard 30-foot or larger boat

$300 $99

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Chicago Sailboat Charters: Luxury First-Class Sailing for Two or Six from Chicago Sailboat Charters (Up to 50% Off)

Luxury First-Class Sailing for Two or Six from Chicago Sailboat Charters (Up to 50% Off)

Chicago Sailboat Charters

Chicago

Captains ferry groups of up to six onto Lake Michigan for relaxing excursions and stunning views

$199 $99

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Select Local Merchants

  • Denna Lawn and Marine
    Get your sea legs ready! Denna Lawn and Marine in Bensenville provides quality vessels so you can have a boating experience that is both relaxing and fun. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    560 N York Rd
    Bensenville, IL US
  • Wilmette Park District
    Nature lovers will appreciate Wilmette's Wilmette Park District. From front kicks to roundhouses, these kickboxing classes will teach you the fundamentals. Parking is plentiful, so guests can feel free to bring their vehicles.
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    200 Lake Avenue
    Wilmette, 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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    2112 Jackson Avenue
    Evanston, IL US
  • Boater's World Discount Marine Center
    Cast away all your troubles and take a relaxing boating trip with Boater's World Discount Marine Center in Schaumburg. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    697 East Golf Road
    Schaumburg, IL US
  • SideTour - Leisure
    Sound Excursions describes their carefully curated group experiences as "field trips for adults." It's easy to see why: every outing takes groups to a new realm of Washington, whether it's the frothy shores of Puget Sound, inland forests and mountains, or tables at Seattle's thriving restaurants. The events held at these diverse locations range from culinary workshops on topics such as sushi-making and moonshine-tasting, to adventurous excursions with whitewater rafting or kayaking, to laid-back themed party cruises. For many outings, luxury transportation is provided.
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    111 North Avenue
    Highland, IL US
  • Marine Navigation
    If it's the boater's life for you, you'll want to check out the incredible seaworthy vessels for rent at Marine Navigation in La Grange. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    613 S La Grange Rd
    La Grange, IL US

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