Would you like to get away from it all for a few hours? What about acharter sailing adventure on the lake with a professional captain as your sailing master and host? At Chicago Sailing we provide you and your guests the opportunity to enjoy a personal holiday for as long as you choose.

Your licensed charter captain will do all the work. You and your family and friends are free to sit back and enjoy Lake Michigan in comfort and safety. Or, take the helm and control your own destiny as captain of your ship.

Our charters are a creative alternative for entertaining important clients in a casual, outdoor setting. Sailing is easy for everyone to enjoy, regardless of his or her sailing experience. It is a great way to involve all members of your group in an activity that requires no level of proficiency.

We can provide the setting for that perfect date, an adventure that will remain a special moment forever. Chicago Sailing Charters have hosted many romantic occasions (and yes, a few marriage proposals). They are also an enchanting way to celebrate an anniversary, bachelor(ette) parties, showers and birthday parties.

We offer charters to fit your needs on a variety of boats. Choose from our J/22's, our J/30,and T-10 and our three Hunter 326's or our luxury Catalina 390.

J/22s are perfect for groups up to four who are looking for the thrill of zipping along on a performance keelboat. It is popular for its ease of handling and sports-car feel. J/30s are roomier, offering cabin space for a greater degree of comfort.  the J30 & T-10 accommodate six adults. The Hunter 326's offer additional room, luxury and comfort designed to a level not normally associated with charter boats.

The Catalina available for that very special occasion, when nothing but the best will do. She is a blue water yachts with sailing accommodations for up to 12 adults.