Sail Charters

Charter Party with FairwindEnjoy the breathtaking sights of one of the world’s most spectacular sailing venues from your own captained yacht.

Fairwind offers pleasure sails with our highly experienced Captains for parties of up to six passengers. All Fairwind Captains are licensed by the U.S. Coast Guard and hold current First Aid and CPR certifications. With Fairwind, your safety is always our number one priority.

Sail a sunset cruise on Lake Michigan with Fairwind SailThere is nothing like a sail along Chicago’s magnificent lakefront. During the day the skyline shimmers like a mirage, the city laying quiet before you as all you hear is the water streaming by your yacht. At night the city lights blink awake to sparkle the imagination. Whether you are a first-time visitor or a life-long Chicagoan, it is an experience you will long remember.

Visit the world-class Field Museum, Shedd Aquarium, and Adler Planetarium and then cap your day with a relaxing sail along the lakefront. All of these attractions and more (Soldier Field, Grant Park, Buckingham Fountain) are within easy walking distance from Fairwind’s docks.

Charter Rates

Private sail charter for up to 6 passengers $395/two hours; $195/hour per add'l hr
Wednesday/Saturday fireworks charter $695
Air and Water Show $1100 (10:00 a.m. – 3:00 p.m.)
Please note: all charters subject to 9% Chicago Amusement Tax

For a special treat, try one of Fairwind’s Fireworks Sails. On Wednesday and Saturday evenings from June 1 through Labor Day, the City of Chicago hosts fireworks off Navy Pier. Enjoy a sunset sail and then celebrate the evening with a grand finale!

Chicago Air & Water Show 2011Chicago’s wonderful lake front also offers the perfect private viewing spot for the July 3rd fireworks and the incredible Air and Water Show.

Fairwind’s pleasure sailing charters make great gifts. Celebrate family and friends with a memorable Fairwind sail. Or reward that special company achievement with a private charter.

Fairwind is also your best choice for corporate team building events. Past customers include CIGNA, Eli Lilly, and Boston Beer Company (makers of Sam Adams beer). For an unforgettable corporate event contact us for details.