Choose Between Two Options
- $99 for luxury first-class sailing for two ($199 value)
- $299 for luxury first-class sailing for six ($597 value)
Sailing trips are 2.5 hours long, and take place on Monday, Tuesday, Thursday, and Sunday evenings, or Saturday and Sunday mornings.
Chicago Sailboat Charters
The minds behind Chicago Sailboat Charters share their passion for the sailing experience by making waterborne adventuring accessible to the general public with group sailing charters. Fostering the atmosphere of a private charter, the captains ferry passengers out onto Lake Michigan for stunning views of Chicago's skyline. The crew encourages its guests to make the most of the trip by providing a bathroom, bottled water, ice for drinks, and plenty of cooler and storage space, while encouraging guests to bring their own, snacks, drinks, and an inflatable blanket for a picnic out on the lake.