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LUXURY ACCOMODATIONS
Our sailing yachts accommodate 1 to 10 people. We offer charters with captain and crew for groups up to six (6) or a bareboat charter for groups up to ten (10) with a USCG Licensed Captain paid separately. With up-to-date amenities and two bathrooms onboard, we assure the comfort of all our guests.
CUSTOMIZED CHICAGO SAILING CRUISES
All private Chicago sailboat charters depart and return according to your schedule. All Chicago sailboat cruises have three-hour minimums. Charter extensions are available upon request. Yes, we encourage you to bring food and refreshments, including alcoholic beverages.
SAFETY
CONCERNS
Our yachts are professionally maintained and equipped. In addition, we certify, train and employ United States Coast Guard Captains with over 20 years of experience. Because of this, rest assured that you are in excellent hands. Also, all of our captains are enrolled in USCG mandated drug screening programs.
CONVENIENCE
FOR YOU
The yachts are at the North End of Belmont Harbor, just east of Wrigley Field—or 15 minutes from the Chicago Downtown area. Windy City Sailing is easily accessible via Uber, Lyft, taxis, and bicycles. Also, parking is available via the City of Chicago. Gift certificates are available for all Chicago sailboat cruises and bareboat charters.
We confirm reservations with a 50% deposit, fully refundable with a seven-day notice.
Gratuity is at your discretion (we recommend 20% to our outstanding crew).
SPECIAL EVENT YACHT CHARTERS
4th of July Sailing Charter
Each year, the Fourth of July Sailing Charter gives the citizens of Chicago the chance to witness some of the nation's most spectacular firework displays from the comfort of a boat. The tour has become increasingly popular and is one of the highest rated Independence Day activities.
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Chicago Air Show Charter
Chicago Air and Water Show is a remarkable event that has long been captivating city dwellers. By taking a sailboat charter from us, you can experience the show from the lakefront. You won't need to fight the crowds for the best view, as you will be luxuriating on your yacht with an unparalleled outlook of the show.
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Navy Pier Fireworks Charter
During summer, the Navy Pier gives us breathtaking firework shows. For an unforgettable experience, there is no better way to appreciate these amazing visuals than to charter a yacht . Our dedicated captains and crew members make sure that all your needs are taken care of, so you don’t have to worry about anything else. With our exclusive amenities, it is not even worth considering any other way to view these displays.
BOOK YOUR CHICAGO SAILING TRIP NOW
WITH WINDY CITY SAILING
We know you will have questions about sailing charters, so feel free to reach out via phone or email.
Please contact Edwina at 773.868.0096 or edwina@windycitysailing.com for details and pricing.
WHAT OUR CUSTOMERS SAY
What a fun afternoon sailing with an amazing Captain Josef! Extremely knowledgeable, friendly and AWESOME!!! His sailing professionalism made our experience fun and thrilling! The views of Chicago’s amazing shore and skylines are breathtaking!
Thank you Windy City for this amazing Summer afternoon, we can’t wait to be back!!
Elizabeth E.
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