Feel the breeze at your back while you avoid getting hit in the face by the boom (is that what it's called?)


Preferred Providers

⛵Two Brothers Sailing

📍Montrose Harbor

⚡Two Brothers Sailing offers sailing lessons, private group events, themed rides, sunset rides and more.

✔️Check out their charter packages 👉 here.

⛵‍ Chicago Sailboat Charters

📍 Belmont Harbor

⚡Chicago Sailboat Charters provides great variety, service, and value for any sailing experience you desire. With many sailboats to choose from, they can arrange the perfect sail to meet your wishes and fit your budget. Whether you are looking for a sailing trip for a few teammates, or a sailboat for up to ten people, they are open every day of the week and will be sailing any time you wish from early in the morning until late at night. They offer night sailing and fireworks sailing, too!

✔️Check out the events 👉 here.

⛵‍Chicago Sailing

📍 Belmont Harbor

⚡Chicago’s premier sailing school and charter facility. With a wide array of offerings, they are a complete one stop shop for all of your sailing needs. No matter what your sailing goals are, they will work with you to get you out on the water!

✔️Book a lesson (they offer lessons for all levels) 👉 here.

✔️Book a private charter 👉 here.

✍️ Add a provider

📍 Anywhere

⚡Don’t see what you’re looking for, or have something specific in mind? Get in touch with us and we’ll work with you to find something that fits your needs.

Get in touch 👉

🤷‍ Don't want to plan?