All Private Yacht Charters

Spend an unforgettable anniversary on board with Windy City Sailing. Our team is dedicated to giving you and your loved one a private charter sailing experience like no other. Witness the sunset while taking in the spectacular views of Chicago, the firework show of Navy Pier from the lake, or simply take the opportunity to enjoy one another's company while peacefully sailing.

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If you're looking for an exciting way to celebrate your birthday, look no further than a private birthday sailing charter. Our professional crew will take care of every detail, leaving you free to enjoy the beauty of the Chicago sunset or fireworks show with your friends. A sailing cruise is the perfect way to make sure your special day is remembered for years to come.

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Have a larger gathering? You can experience Chicago's majestic skyline with the luxurious touch of sailing a private yacht! Bareboat Chartering, also known as Demise Chartering, can accommodate up to ten people, and you provide your own food and drinks. Start planning your excursion and make it an unforgettable memory.

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To make a lasting impression on your clients, consider taking them on a client charter or company cruise. Doing so ensures that you don't take them to a crowded, noisy restaurant or sporting event. It is an effective way of conveying to them that you prioritize their time and are serious about your business. Our charters along the Chicago Lakefront offer unparalleled privacy and comfort. Show your attention to detail and sophistication with a memorable cruise.

Celebrate your bachelor or bachelorette party with a sailing adventure aboard Windy City Sailing! Make lasting memories and explore the picturesque shores of Chicago from the decks of the Nebula yacht. Indulge in the tranquility of the lakefront or use it as the perfect place for a grand celebration; the choice is yours!

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Making a proposal an unforgettable memory is something both of you will cherish for a lifetime. Experience a romantic occasion by taking a private proposal charter from Windy City Sailing. You can create an amazing backdrop of the gorgeous Chicago skyline or bask in the color of bursting fireworks for a spectacular atmosphere. And if you desire a more intimate setting, the options of morning, afternoon, or evening excursions can help you make your proposal one to remember.

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