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Writer's pictureIan Malanes

Why Choose Windy City Sailing for Your Private Yacht Charter Experience?

Looking for a top-notch luxury yacht charter in Chicago? Look no further than Windy City Sailing! Whether you're seeking an escape hosting an event or celebrating with family our exceptional service and top-of-the-line amenities guarantee an unforgettable experience on Lake Michigan.

View of the city and lake from the yacht

Our yacht at Windy City Sailing boasts a well-maintained yacht with state-of-the-art features like decks, elegant interiors, and advanced navigation systems. From the sailboat to the motor yacht, we have the perfect vessel to suit your preferences.


We believe that each yacht charter should be personalized to your liking. Our dedicated team collaborates with you to customize every aspect of your journey from planning the route to arranging catering. Whether you desire a sunset cruise, a sailing trip, or a lively celebration we make sure your dreams become reality.


Count on our crew members who are dedicated, to delivering service while prioritizing your safety and comfort throughout the voyage.

Our team has an understanding of Lake Michigan and the Chicago shoreline offering insights and recommendations to elevate your charter experience ensuring each journey is not only enjoyable but also educational.


Breathtaking Scenery and Excursions

Sailing with Windy City Sailing promises vistas of Chicago's skyline and access to stunning destinations along Lake Michigan. Take in the city's landmarks from a perspective explore neighboring harbors or drop anchor at picturesque spots for a swim or picnic. Our charters deliver a blend of leisure and excitement allowing you to discover Chicago in a new light.


Suitable for Every Occasion

Windy City Sailings private yacht charters are ideal for events. Whether you're planning a wedding celebration marking a birthday milestone or organizing an impressive corporate gathering for clients our diverse fleet and customizable packages cater to all occasions ensuring an exceptional experience for both you and your guests.


Environmentally Conscious Practices

We are dedicated to preserving the environment and the beauty of Lake Michigan. Windy City Sailing implements eco practices such as operations and waste reduction initiatives to minimize our impact on the environment while promoting responsible yachting.


Feedback from Our Clients

Let our satisfied customers do the talking—their positive experiences speak volumes about the service we deliver.

Check out the reviews and testimonials to discover why Windy City Sailing stands out as the pick for yacht charters in Chicago.


City lights and a the lake at night

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