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PRIVATE YACHT CHARTERS
Offered by Windy City Sailing
Experience Chicago like never before with a private yacht charter on Lake Michigan. Windy City Sailing offers customized excursions tailored to your group, whether you're planning a romantic sunset cruise, a special celebration, or an unforgettable event on the water. Our private yacht charters combine stunning skyline views, professional captains and crew, and the freedom to explore Chicago’s iconic shoreline at your pace. From Navy Pier firework cruises to bespoke corporate outings, every charter delivers comfort, luxury, and memories that last a lifetime.
Anniversary
Charter
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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Bareboat
Charter
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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Bachelor or Bachelorette Sailing Charter
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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Birthday
Sailing Charter
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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Client
Charter
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.
Proposal
Charter
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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4th of July
Sailing Charter
Each year, the Fourth of July Sailing Charter gives the citizens of Chicago the chance to witness some of the nation's most spectacular firework displays from the comfort of a boat. The tour has become increasingly popular and is one of the highest rated Independence Day activities.​
Chicago Air Show
Yacht Charter
Chicago Air and Water Show is a remarkable event that has long been captivating city dwellers. By taking a sailboat charter from us, you can experience the show from the lakefront. You won't need to fight the crowds for the best view, as you will be luxuriating on your yacht with an unparalleled outlook of the show.
Navy Pier
Firework Charter
During summer, the Navy Pier gives us breathtaking firework shows. For an unforgettable experience, there is no better way to appreciate these amazing visuals than to charter a yacht . Our dedicated captains and crew members make sure that all your needs are taken care of, so you don’t have to worry about anything else. With our exclusive amenities, it is not even worth considering any other way to view these displays.