INSTRUCTION

Sail Chicago offers an affordable way to learn to sail in Chicago. Each of our on-the-water sailing courses gives you the knowledge and skill to put you on the road to being a competent and confident sailor.

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What class is right for me? All students and members must first complete a Sail Chicago Pre-sail Orientation and the US Sailing Basic Keelboat Online Course before their first on-the-water class. Once those are complete, students will complete 3 levels of on-the-water courses in succession. Each course takes place once weekly over 4 weeks. Students with experience sailing may advance through the program more quickly with permission. All of our classes are taught by volunteer instructors who are passionate about sailing.

  • All students are required to attend a PSO session before beginning their first on-the-water class.

    PSO gives new students and new members an introduction to sailing on Lake Michigan and the workings of Sail Chicago. As a sailing cooperative with over 300 members, it is important for everyone to do their part in adhering to the guidelines and maintaining standards of Sail Chicago.

    Topics include:

    Introduction to Sail Chicago

    You have registered for a class on-the-water – Now What?

    Preparation for sailing on Lake Michigan

    Day 1 of Sailing on-the-water class

    Q&A

  • All students must demonstrate knowledge of fundamental sailing skills and terminology. The best way is to take the US Sailing Basic Keelboat Online course. We encourage prospective students to learn as much as they can ahead of their course date in order to get the most out of on-the-water class. Students can request access to this course once they have registered for a Sail Chicago on-the-water class.

  • On the water, students will convert classroom concepts into actual sailing experience in this beginner class. Classes are conducted on our fleet of Colgate 26 sailboats and are held at Chicago’s Monroe Harbor in downtown Chicago. Students will learn to maneuver a keelboat upwind and downwind in open water using tacking and jibing maneuvers while maintaining  proper sail trim as appropriate. Check out the class syllabus . 

    Cost $320

  • Flexible, expert advice when you need it. Book hourly support across a range of topics—from planning to problem-solving. This focused consultation will help clarify your goals, map out next steps, and identify opportunities for growth.

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Classes for experienced Sail Chicago Members:

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Register

Before you register, here are some important things to know.

Please read our Class Registration and Cancellation Policy before registering for any class.  Most common questions about our classes are addressed in this document.

On-the-water classes are only be offered to members of Sail Chicago. Learn about the cost of membership and the benefits you’ll enjoy on our membership page.

The U.S. Sailing Basic Keelboat online course is essential to our curriculum and the best way to meet one of the prerequisites for our classes. Students with no other proof of basic sailing knowledge must take this online course, begin learning and finish the quizzes before taking their first on-the-water class. Students will receive instructions on how to register for the online course once they register for a Sail Chicago on-the-water course.

Sail Chicago is a US Sailing accredited sailing school, which means you can be sure that you're learning to sail the right way, with qualified sailing coaches and well-maintained boats. 

Frequently asked questions

What is the class Lottery?

Due to the popularity of our classes, we have developed a lottery system for registration. Information about the lottery can be found on the registration page.

Does having a membership increase my odds in the lottery?

No. Having a membership does not increase your odds nor does having been a member in previous seasons.

Wait, I only have 24 hours to register for a class?

No. You can register any time after registration opens up for your group.

The class I wanted wasn’t available. Should I just sign up for the next one?

Please see our Class Registration and Cancellation Policy under the heading “Selecting the Appropriate Course”

I took class X last year and want to retake it. How do I fit in?

Requests to retake a course will be dealt with on a case-by-case basis. Similar to last season, there will be a form (to be linked once it’s created) for these requests.

I have prior experience, I want to skip Crew and take an advanced course.

If you have not taken a class with us before, you will need to go through the General Lottery or wait until classes have opened to everyone. Last season there were still a handful of seats left in the Skipper Prep classes.

I’m in Group X and none of the available classes fit my schedule!

Unfortunately, that’s the way things go sometimes. Our lottery grants the chance to Register for a course, not for the course itself.

I want to take a class with my partner!

With the way the lottery runs, we can’t guarantee you’ll be able to get into the same session.

What about Cruising Courses?

This plan only pertains to our Learn-To-Sail Curriculum (Crew, First Mate, Skipper Prep). Cruising courses will be announced and rolled out separately.

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Keep up to date on events, schedules and when to register for classes by following the Telltale.