How Much Does a Chicago Sailboat Charter Cost?

Planning a private sailboat charter on Lake Michigan and wondering what it will cost? Windy City Sailing charters are priced by the hour, which makes it easy to plan around your group size and the day you want to sail.

What is included

For groups of up to six guests, the hourly rate includes a licensed captain, crew, docking fees and taxes. Groups of seven to ten guests can sail aboard Nebula, our 40-foot sailboat, under a bareboat charter agreement in accordance with U.S. Coast Guard regulations. For those larger groups the captain fee is not included in the hourly rate.

Hourly rates for up to six guests

Monday through Friday charters are $250 per hour with a three hour minimum. Saturdays, Sundays and holidays are $275 per hour with a three hour minimum. Wednesday evening fireworks charters are $275 per hour with a three hour minimum, and Saturday fireworks charters at Navy Pier are $275 per hour with a 3.5 hour minimum.

Hourly rates for seven to ten guests

Monday through Friday charters for larger groups are $300 per hour with a three hour minimum. Weekends, including Saturday fireworks, are $350 per hour with a three hour minimum. The captain fee is not included for these larger groups.

Special events

Special event charters, including the Fourth of July and the Chicago Air and Water Show, are $400 per hour. These dates book early, so reserve as soon as your plans are set.

How to plan your budget

Because the three hour minimum applies, a typical weekday charter for up to six guests starts at $750 and a typical weekend charter starts at $825. Splitting the cost across your group often makes a private sailboat charter comparable to a nice dinner out, with the Chicago skyline as the view. Guests are welcome to bring their own food and drinks, and life jackets are provided for children.

Ready to sail? Visit the Sailing Charter Rates page at windycitysailing.com or tap Book Now to choose your date. Our team has been welcoming guests aboard from Belmont Harbor for two decades.