Riverside, Illinois, United States
Fairwind Sail Charters is situated in Riverside, Illinois, offering a relaxed and friendly environment for sailing enthusiasts. With nearly four decades of experience, the school emphasizes safety and seamanship, providing quality instruction on Lake Michigan, which offers a unique fresh water sailing experience reminiscent of blue water cruising. Whether students are interested in chartering in destinations like St. Somewhere or considering boat ownership, Fairwind Sail Charters aims to support sailors at all levels in a welcoming setting.
Contact for pricing
Contact for pricing
Contact for pricing
Located along the Des Plaines River in Riverside, Illinois, our school offers a convenient setting for learning to sail just outside Chicago. The nearby waterways provide an accessible environment for beginners to gain confidence and develop their seamanship skills. Our instructors focus on safety and practical sailing techniques, ensuring students build a solid foundation whether on small dinghies or larger cruising sailboats. The area’s calm waters and scenic surroundings make it an ideal place to start your sailing journey. With a well-equipped fleet and experienced staff, we guide students through fundamental skills, navigation, and boat handling in a relaxed yet professional setting. Our location is perfect for those looking to learn in a comfortable environment close to the city.
Fairwind Sail Charters is conveniently located at 147 Bloomingbank Road in Riverside, Illinois. If you're flying in from afar, the closest major airport is Chicago O'Hare International Airport (ORD), approximately a 20-minute drive away. Upon arrival, you can rent a car or use ride-hailing services like Uber or Lyft to reach the school. From the airport, simply take the I-90/I-294 east to the River Road exit, then head south to Bloomingbank Road. If you're traveling from Chicago's downtown area, you can also consider renting a car or taking a ride-share directly to the school, enjoying a relaxed drive through scenic suburban surroundings. Once you arrive at 147 Bloomingbank Road, you'll find our location easily accessible and ready to set sail.
The best time to sail in Riverside, Illinois, is from late spring through early fall, with warm temperatures and calm waters making for ideal conditions. Late June through August typically offers the most reliable weather for a comfortable and enjoyable sailing experience.
No reviews yet. Be the first to share your experience!
See something wrong or have a question? Message us at hello@sailingtree.com

60605, USA
Spinnaker Crew Sailing is dedicated to helping individuals explore their passion for adventure on the water. Located on Lake Michigan in Chicago, their team of experienced, ASA-certified instructors offers a range of sailing courses designed to build confidence and skills, whether you’re just starting out or looking to advance your knowledge. The school’s relaxed, friendly atmosphere makes learning fun and accessible, with beautiful views of the city skyline and lakefront serving as the perfect backdrop for your sailing journey.

Wilmette, Illinois, United States
Be-Nautical is a welcoming sailing school located in Wilmette, Illinois, offering a variety of courses to suit all skill levels. Whether learning individually, as a couple, or with family, students can explore everything from basic sailing to advanced navigation and weather forecasting. The school provides hands-on training through classroom instruction, practical courses, and experiential learning, including racing, night sailing, and cruising skills. With multiple Chicago area harbors as training locations, Be-Nautical also offers special programs like flotillas, offshore sailing experiences, and certifications, all in a relaxed setting that encourages learning and adventure.