Chicago Sailboat Charters

Private Charters

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Chicago Sailboat Charters provides the best variety, service, and value for any sailing experience you desire. With many sailboats to choose from, we can arrange the perfect sail to meet your wishes and fit your budget. Whether you are looking for a romantic sailing trip for two, or for a sailboat for up to ten people, we are open every day of the week and will be sailing any time you wish from early in the morning until late at night.

SUNNY DAY Insurance
(to see cancellation policy without insurance click here). Please note that for ALL sails (regardless of insurance), if there is persistent rain and/or lightning, we do not sail, and there is no cancellation or rescheduling fee.
We know that some people may need an 80+ degree and no clouds day, and others may only care about being out on the water, even if it it 65 degrees and cloudy. For those of you that need to be sure that the forecast calls for the conditions you desire, you can purchase our sunny day insurance. We can control just about everything to make your sail fantastic, but we can't control Mother Nature! So if you are planning a special event that has to be just right, this may be for you.

(Not available for special events)

Sunshine Insurance Terms (to see cancellation policy without insurance click here)

The fee is 30% of the cost of the charter.

Insurance must be purchased at least 10 days in advance of your sail.

You may cancel up to 8 hours prior to the sail for any reason at all, and pay nothing except the insurance. You may cancel by calling us (you can leave a voicemail) or by emailing us.

The insurance fee is non-refundable.

Not offered for special events, or rentals for more than 6 people.

Chicago Sailboat Charters 773-236-7245
info2011@ChicagoSailboatCharters.com