Behind every great sailing experience is a vessel that captures the spirit of the sea, and for Windy City Sailing, that vessel is the...

There’s a unique magic that happens when you leave the shore behind and see Chicago from the deck of a sailboat. From the water, the city...

The bachelorette party is one of the most cherished celebrations leading up to a wedding, and it deserves to be unforgettable. While...

There’s something inherently magical about celebrating on the water. Whether it’s a birthday , anniversary, product launch, or...

Every couple has a unique love story, and what better way to celebrate yours than with a romantic sailing charter aboard the Nebula ?...

There’s something special about sailing in Chicago . It’s not just the skyline, or the breeze off the lake, or even the way the sun sets...

At Windy City Sailing , every charter aboard the Nebula is more than just a boat ride — it’s an experience crafted by two passionate...

Chicago is a city that truly shines during the summer months. With festivals, music, food, and fireworks lighting up the skyline, there’s...

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,...