Lake Michigan offers more than just stunning views—it’s the perfect backdrop for creating lifelong memories with friends, family, or...

1. Years of Expertise on the Water Our captains bring decades of combined experience to every sailing excursion. Whether they’re...

When creating unforgettable memories on the water, there’s no better choice than Windy City Sailing. Our flagship yacht, the Nebula, is...

There’s nothing quite like gliding across the sparkling waters of Lake Michigan aboard a sailboat, especially when you’re sharing the...

Embarking on a voyage on Lake Michigan alongside Windy City Sailing is an opportunity to take in the Chicago skyline and the serene...

When planning a memorable day on the water, choosing the right charter company can make all the difference. Whether you're celebrating a...

Starting out on your sailing voyage can bring a mix of excitement and a touch of nervousness. At Windy City Sailing we aim to ensure you...

Celebrating your wedding anniversary is an occasion that deserves an unforgettable experience. Picture commemorating this milestone on...

Looking for a top-notch luxury yacht charter in Chicago? Look no further than Windy City Sailing! Whether you're seeking an escape...

Experience the magic of observing the Chicago Air Show from the setting of a yacht! Say goodbye to the crowded beaches. Come aboard for...

Welcome to the summer guide for 2024 in Chicago also known as the Windy City! There are plenty of events amazing attractions and endless...

In today's paced world it's crucial to find ways to unwind and take care of your well-being. Sailing offers a blend of peace, excitement,...

The 4th of July is a time to come together show patriotism and create lasting memories, with loved ones. This year elevate your...

Picture yourself marking a moment surrounded by the views of Chicago's skyline and the calm waters of Lake Michigan. Whether it's a...

Lake Michigan, known as the gem of the Midwest is more than a body of water with picturesque views. Along its shoreline lie hidden...

Welcome to the sailing season on Lake Michigan! With the arrival of weather and calm waters now is the time to immerse yourself in the...

When it comes to creating memories there are things that can compare to a Navy Pier Firework Cruise with Windy City Sailing. Imagine...

Organizational getaways and team-building exercises are crucial, for promoting collaboration lifting spirits, and improving efficiency....

When it comes to summertime in Chicago there's nothing like the excitement and beauty of watching the Navy Pier fireworks display from...

When thinking about renting a yacht in Chicago timing plays a role. Chicago's yachting season provides views of the city skyline and...