Choose Between Two Options
- $99 for first-class sailing for two ($199 value)
- $299 for luxury first-class sailing for six ($597 value)
Sailing trips last for 2.5 hours, and take place on Monday, Tuesday, and Thursday evenings at sunset, or Saturday and Sunday mornings. All outings take place on 36'-39' boats, with the six-person outing guaranteed to take place on a 39' boat.
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.
91% of 23 customers recommend
“Be early, bring extra warm clothes and be ready for a great time on the water. Excellent Captains, Rob and Cory!”
“We enjoyed a lovely cruise out on Lake Michigan.”