Windy City Sailing provides many options for your yachting pleasure. The most popular excursions are the private sailboat charters for 1-10 passengers and the power yacht charters for 1-6 passengers. Our sailing and power yacht firework charters to Navy Pier provide spectacular overhead displays on Wednesday and Saturday nights. Major attractions include July 4th fireworks, Chicago Air & Water Show, Jazz Fest, Blues Fest and Taste of Chicago. The best way to see Chicago is on a Lake Michigan cruise so charter a yacht and arrive in style!
Special occasions and holidays become fantastic when enjoyed on a yacht. Proposals, family reunions, marriages, birthdays, and other celebrations are memorable with Windy City Sailing!
View Terms and Conditions
Terms and Conditions
What is your cancellation policy?
We have a seven (7) day cancellation policy. If you cancel within seven (7) calendar days of your reservation will result in forfeiture of your deposit. If you cancel outside of seven (7) calendar days of your reservation the deposit will be refunded less a $50.00 service fee. We wish we could just sail for fun all the time but our business partners mean business. Thank you for understanding.
What is your rescheduling policy?
Our rescheduling policy is very simple: If you reschedule within seven (7) calendar days of your reservation there is a $100.00 rescheduling fee. If you reschedule outside of seven (7) days of your reservation date and there may be a $50.00 rescheduling fee.
Weather and “Captains Call”
Weather is part of the sailing experience – both the good and bad days. We must respect Mother Nature and we will not put anyone in danger. The Captain makes the final determination whether or not to sail. WCS has no liability or responsibility for delays, cancellations or failure to furnish services when caused by Acts of God, inclement weather, rough seas, storm warnings, lightening, thunderstorms, heavy fog, very strong winds, government orders, labor disputes, legal prohibitions, third-party interferences, or any other causes beyond the control of our Captains or WCS. When possible cancelled charters will be rescheduled. If this cannot be done due to time or other constraints, any deposits will carry over to the following year or we will provide a full refund.
In addition, the Captain may exercise good judgment and discretion to cancel any charter without refund for any of the following reasons: passengers over-intoxicated, unconsciousness, aggravation of previous injury, illegal drug use, unruly or reckless behavior, perceived risk or threat to the operation of the boat or to others, criminal act or violation of local law and boating regulations, or behavior that distracts the Captain or Crew from their duties.