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.

Private Sailing Charters on our Chicago Boats

Day sail charters - Chicago boat trips in the sunshine, bring a lunch (and beverages of your choosing…). If you choose, go for a swim in the breakwater protected playpen or offshore in the waves of Lake Michigan.

Night sails - Watch the sunset and enjoy the night skyline on one of our night Chicago boat charters. Watch the sun set over the city from our boat, and the Chicago skyline light up! This is a peaceful way to spend an evening.

Fireworks sail charters - From May through September Navy pier puts on beautiful fireworks displays Wednesday and Saturday night. We sail our boat to Navy Pier so you can experience them close up from the water away from the crowds. Chicago also has several other fireworks nights, please see our fireworks page.

Moonlight sailing charters- On a few nights per month during the Chicago summers, the moon rises over the lake in a beautiful way. Come sail on our boat and see a Chicago moonrise in style.

Bed & Breakfast sail- Spend the night on our boat, and go for a morning sail to enjoy to enjoy the Chicago skyline.

Special event charters - Chicago has many special events that are best taken in from a boat. Come out on Venetian night or 3rd of July for the two best fireworks shows in the city. Spend the day anchored down out in front of North street beach to get the best view of the Chicago Air and Water show you can get (unless you are in one of the planes). The Chicago to Mackinac race day is a spectacular event to see from the water, hundreds of boats starting their race towards Mackinac Island. In 2010 when the tall ships come to Chicago, see them close up as they make their way to Navy pier in the Chicago Tall Ships parade.

Northerly Island Concerts sails - We sail to Chicago's Northerly Island (by the Shedd Aquarium) right near the stage. You can hear the show perfectly from our boat, and see the big screen.

Personalized sails - Tell us what you want, we will make it happen! Enjoy Chicago from our boat for your special occassion.

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