.png)
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
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
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).
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.
Frequently Asked Questions
Have you ever wanted to sail but were unsure what it would cost to charter a private yacht? If so, Windy City Sailing is here to help with all your sailing–related questions. We have made things easy to find by categorizing our questions, and if there’s anything you can’t find, feel free to reach out. Our knowledgeable staff is here to answer all your questions about sailing along the wonderful Chicago Lakeside. From planning the perfect corporate outing for out-of-town guests to helping you witness the incredible 4th of July fireworks, we have it all covered!
Review our FAQ
Preferred Partners
Preferred Partners are the resources we depend on to deliver the highest quality service to our guests. We value them and appreciate their services.
WHAT OUR CUSTOMERS SAY
Leave us a review on Google. Leave us a review on Trip Advisor.