Sailing in Oak Park, IL


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-Hour Sailing Charter for Up to Six from SeaBreeze Charter (50% Off). Two Options.

SeaBreeze Charter LLC

SeaBreeze Charter LLC

American Sailing Association–certified captain entertains passengers during two-hour charters on Lake Michigan; BYOB and food

$356 $179

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

Three-Hour BYOB Cruise or Four-Hour BYOB Fireworks Cruise for Up to Six from Celestial Sails (UP to 64% Off)

Celestial Sails

31st Street Harbor

Explore Lake Michigan aboard a 44-foot Beneteau Oceanis yacht; fireworks cruises include choice views of Navy Pier pyrotechnics

$250 $99

Semi-Private Sunset Cruise for Two or Basic Intro to Sailing Course at Chicago Yacht Share (52% Off)

Chicago Yacht Share

Lakeview/Lincoln Park

Instructor teaches basic sailing techniques to complete novices on Lake Michigan; couples enjoy a romantic sunset cruise

$400 $190

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

2.5-Hour Private, Hands-On Sailing Experience for Up to Six from Smelly Onion Sailing (Up to 41% Off)

Smelly Onion Sailing

Burnham Harbors

Private, hands-on sailing experience lets guests take over the role of the crew and sail the boat; captains teach them basic skills

$550 $325

$499 for Three-Hour BYOB Sailing Cruise for Up to Six on Luxury Yacht from Windy City Sailing ($600 Value)

Windy City Sailing

Lakeview

Take in one-of-a-kind views of Chicago on this three-hour BYOB cruise aboard a luxury sailing yacht

$600 $499

75-Minute Sailing Tour for One Adult with Optional Beverage on Tall Ship Windy (38% Off)

Tall Ship Windy

Navy Pier

A 148-foot-long, traditional four-masted schooner sails throughout Lake Michigan for about 75 minutes

$30 $20

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

$49 for a Mid-Day, Happy Hour, or Sunset Cruise for Two from Nauti Cat Cruises (up to an $80 Value)

Nauti Cat Cruises

Traverse City

Atop the largest commercial sailing catamaran on the Great Lakes, passengers take in the beautiful views and enchanting scents of the bay

$80 $49

One-Year Subscriptions to "Yachting", "Boating", or "Cruising World" Magazines (Up to 50% Off)

Yachting, Boating, & Cruising World Magazines

Online Deal

Get expert insight into the sailing industry & lifestyle with year-round subscriptions of Boating, Yachting, or Cruising World

$12 $6

Select Local Merchants

  • Go Sailing Chicago
    Gliding across Lake Michigan, the sailing party watches the sun sink beneath the Chicago skyline. As the last rays fade from view, the city's skyscrapers throw their light onto the lake's surface. The captain steers the ship past Grant Park and Millennium Park, and then veers out toward Navy Pier, where the ship's passengers find a prime viewing spot for the Saturday-night fireworks show. In addition to charters like these, the captains of Go Sailing Chicago—all holding US Coast Guard Master Captain licenses and certifications from the American Sailing Association and US Sailing—furnish beginner through advanced sailors with sailing gloves and life jackets before leading hands-on instruction in proper seamanship. Launching from DuSable and Monroe Harbor, and sometimes other points along the lakeshore, Go Sailing Chicago's four-boat fleet meets or exceeds the safety standards set down by the USCG and the most persnickety of ship-in-a-bottle builders.
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    400 East Monroe Street
    Chicago, IL US
  • Tall Ship Windy
    The massive schooner gently bobs in the Lake Michigan waters as the Chicago skyline towers on the shore. Onboard, hardy sailors relate tales of piracy as they train their passengers to tie knots and unfurl sails. Period lessons abound onboard Windy, the lone vessel helmed by US Coast Guard-certified captains and crews. The nostalgic steed is used to educate visitors on the lake's maritime traditions and explore coastal waters. Windy also plays host to themed adventures that include fireworks shows, pirates explaining city architecture, and pirates complaining about the popularity of pool noodles. Crews strive to make each tour unique, with sailors who expound on their skills as well as performers and educators versed in history, maritime lore, art, and theater.
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    600 E Grand Ave.
    Chicago, 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 South La Grange Road
    La Grange, IL US
  • Chicago Line Cruises
    Sometimes all it takes is a suggestion. Terry Johnson and Paul McCarthy founded their vessel-chartering business in 1980. But when a good friend recommended they offer expertly narrated tours on the history and the iconic architecture of Chicago, the pair jumped at the opportunity. Praised as the “Best architecture tour available” by the Chicago Sun-Times and “Most engaging tour of the bunch” by Time Out Chicago, their river cruises take passengers on three types of educational, 90-minute tours of the city. Chicago Line Cruises has transported more than three million Chicagoans and visitors along the river for entertainment, stunning views, and a deeper appreciation for architectural design. Architectural Cruises Learn how Chicago became the birthplace of the first buildings to be dubbed "skyscrapers." Hear how the Great Chicago Fire paved the way for an architectural renaissance. See a broad selection of modern architectural styles and discover the distinctive characteristics of each. Experience Chicago's first architectural river cruise. Enjoy a cocktail during one of the evening cruises. Historical Cruises Hear the overarching story of how Chicago transformed from a swampy marshland to a world-class city. Learn about the Chicagoans whose innovations helped influence architecture and commerce around the world. Savor a cup of Starbucks coffee while a guide recounts Chicago's triumphant and tragic moments. Historical tours are presented in partnership with the Chicago History Museum. Chartered Cruises Private outings are available for 20–173 passengers. Full-service bars and professional sound systems are available for special events. Celebrate while savoring views of the Chicago skyline from a different perspective. Choose from three vessels: the Ft. Dearborn, the Innisfree, and the Marquette.
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    465 N McClurg Ct.
    Chicago, IL US
  • Millennium Sailing
    What services does your business offer and what makes your business stand out from the competition? Large, comfortable, 40 ft pristine luxury sailing yacht; fully equipped with everything you need for your party including 2 bathrooms, refrigerator, serviceware, grill, pool toys, and play your own music with an iPod connection. Ice and water is also included. What is the experience customers can expect? Amazing views of the city skyline. Experience the quiet motion of the boat under sail and even take the helm if desired. Captain shares knowledge of local city history & architecture. Watch transformation from daylight to city lights on evening cruises. A safe, fun, memorable summer experience! What was the inspiration to start or run this business? After 30 years of sailing experiences while raising my family and entertaining friends on our sailboat, I wanted to share my love of sailing with others. What do you love most about your job? Sailing itself while making a boat move only under the power of the wind and sails, stimulating conversations with clients, Entertaining guests with humor and knowledge with personal stories while sharing information about the skyline and Chicago history and watching clients enjoy themselves!
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    400 East Monroe Street
    Chicago, IL US
  • Carefree Boat Club Chicago
    Carefree Boat Club was founded on the principle that adventuring on a boat is always more fun without the chores associated with ownership. Over time, the owners gathered a huge fleet of speedboats, pontoons, and sailboats, launching them into prime boating waters from 27 harbors around the nation. They also assembled a team of maintenance experts to care for the vehicles, removing cleanup and repair responsibilities from club members' agendas. Then, they set their membership rules, keeping a strict ration of ten members to every one vehicle in their fleet to ensure easy boating access. Today, the company maintains a fledgling branch of their operation out of the 31st Street Harbor in Chicago. Their growing fleet already includes a variety of speed boats ready to zip across the smooth surface of Lake Michigan, such as the Sea Ray 240s, 260s, and 270s. In addition to providing unlimited vessel access for members and rentals for non-members, they also arrange a variety of club events at each location. Members go on annual picnics, gather together on holidays, and host seminars for boating-related subjects such as safety, navigation, and how to trick everybody into calling you admiral.
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    3155 South Lake Shore Drive
    Chicago, IL US

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