About Us

Skyline Charter Yachts was born from a lifelong love of boating and a desire to share Chicago’s most breathtaking views from the best seat in the city—the water.

Founded by a seasoned hospitality and marketing professional (and lifelong boater), Skyline is more than a charter business. It’s a curated experience designed for people who appreciate comfort, privacy, and personalized service. Every detail—from how you book, to how you’re greeted, to the memories you leave with—has been thoughtfully designed to exceed expectations.

We operate on a bareboat charter model, which means you rent the yacht and select your own U.S. Coast Guard-certified captain from a trusted list. This gives you more flexibility and a private, customized outing every time you set sail.