FAQs

Questions about classes.

  • Information can be found at: https://www.sailchicago.org/2024-course-registration

  • Tiller Times, hosted by volunteer certified Sail Chicago Skippers and instructors, are a chance for current sailing students to get a chance to practice their new skills on the water with other sailors. Tiller Times are a benefit of Sail Chicago membership that are available to current students and those that have been students in the past calendar year.

    Students and recent students can sign up for seats on Tiller Time sails on the membership website under the Seat Reservation page.

  • Currently we do not offer classes in locations other than Monroe (Colgate & Rhodes) and Belmont/Burnham Harbors (cruising only).

  • You may sign up for a maximum of two (2) Tiller Times at a time. Once you've completed a Tiller Time, you may sign up for more Tiller Times. You may only sign up for a maximum of four (4) Tiller Times each season.

    As Member Cruise Outings become available during the sailing season, you may sign up for as many as you like, however you can only sign up for one (1) at a time.

    The number of Tiller Times and Member Cruise Outings scheduled during the season depends entirely upon the number of volunteer skippers who make themselves available.

  • Sail Chicago doesn't have waterfront space, so members and students meet on the south edge of dock space at Monroe and Lake Shore Dr. Here's a map. The address for google mapping is 400 E. Monroe Ave. to get you close, but make sure you're on the south side of the dock.

  • Item descriptionAs a 501(c)(3) non-profit organization, our mission is to offer quality instruction in sailing and boating safety, and to provide affordable sailing opportunities to its members and others in the Chicago area. A benefit of membership in our organization is that members can reserve boats for private use after they have completed the requirements to become a Skipper.

    We welcome experienced sailors, but each member must go through the Skipper qualification process which involves taking our Skipper Prep class. This ensures that all of our Skippers are well-acquainted with our boats, our procedures, and become properly oriented to Monroe Harbor. Successful completion of the Skipper Prep course and course tests will qualify you as a Sail Chicago Skipper, and enable you to reserve Sail Chicago boats for private use. It also makes you eligible to obtain the U.S. Sailing Basic Keelboat certification.

    NOTE: Private boat use is granted based on a Sail Chicago instructor's evaluation of your sailing and boat rigging skills and your knowledge of Sail Chicago's rules & regulations. After passing Skipper Prep, you will also be required to sail with another Sail Chicago skipper for your first three private rentals.

    In rare cases, this requirement may be waived for an individual by the board upon the recommendation of the Safety Director and Lead Instructor. Highly experienced sailors should be prepared to provide their sailing resume for review.

    All Sail Chicago skippers are required to pass our Skipper Prep class, without exception.

  • No, unfortunately at this time we do not have the ability to offer private lessons.

  • Membership dues are non-refundable. Exceptional cases are left to the discretion of the Chair of Sail Chicago (chair@sailchicago.org)

    You can find information about canceled classes, dropping classes, and course refunds in the Sail Chicago Class Registration and Cancellation Policy. Students are required to read and acknowledge this policy when they register for classes.

  • Unfortunately no, we do not offer sailing lessons for children or young adults under the age of 18 at this time.

  • Registration for our classes typically opens up in mid-March, and our classes fill up fast. We make every effort to place all interested students, but as an all volunteer organization, sometimes we simply do not have the instructional bandwidth to offer the number of sessions we would like to.

    For this reason we offer a wait-list for classes which have been filled. As instructor's schedules allow, many times we are able to add additional sessions as the sailing season progresses.

    To register for the waitlist, visit the my.sailchicago.org page and under Instruction there is a is a link to the waitlist

  • Information about each of our classes can be found on our instruction page. You can find more guidance about choosing the right class in the Sail Chicago Class Registration and Cancellation Policy.

General questions.

For racing specific questions, please see our racing page.

  • Send an e-mail to membership@sailchicago.org. Your e-mail address can be quickly and easily changed, and this change will flow down to other systems (mailing list, volunteering, pre- and post-sail checklists) that Sail Chicago uses.

  • The annual membership runs for the calendar year, January 1 to December 31. Usually members can renew their membership by the third week in January.

  • If you're looking for parking close to the Monroe Tender dock, the closest option is the Millennium Park Garage located to the west. It's about a 7 - 10 minute walk to the tender dock from there. Parking rates vary, but it's not cheap. You can also park in a lot or at a meter downtown and walk over to the dock to save money. Of course, public transportation or bicycle remain the most cost effective ways to get to the tender dock.

    If you're reserving one of our boats for private use, there is one parking pass per reservation for the garage that you can use, free of charge. Note, however, that you need to have the pass in hand BEFORE you park in the garage. So you'll need to swing by the dock, grab the pass, and then park your car and walk over. The parking pass for the garage may be used after 10:00 am on weekdays and all day on weekends. Parking passes for skippers are available in a lockbox located outside the Monroe Harbor tender office.

  • Please see our Fleet page for details about our boats. Members who are skipper-certified and checked out on the specific boats may reserve boats for private use when the boats are not being used for other Sail Chicago program activities. Members reserve open boats using our online reservation system. Current costs for private boat use and additional information can be found on the reservation page and vary by time of day.

  • As a 501(c)3 non-profit organization, our primary mission is to teach sailing to the Chicagoland community. Unfortunately, we can only offer private use of our boats to members of our organization who have completed our skipper training program. A variety of other organizations in the Chicago area offer private boat rental.

    However, if you're a member of another Community Sailing Organization, we'd love to connect you with one of our members who could host you for a sail. Please e-mail us at support@sailchicago.org, and we will put you in touch with our Ambassadors program.

  • Besides being able to hang out with some really good sailors, not to mention genuinely nice people, membership benefits include:

    Access to Sail Chicago (US Sailing-certified*) instruction classes,
    Access to sailing opportunities through Tiller Times (students only) and Member Cruise Outings,
    Fun social events throughout the year
    Participation in an active community of like-minded people dedicated to the sport of sailing
    Access to a fleet of well-maintained boats (skipper certification required).
    A place to learn new skills and put your existing ones to work.

  • YES! Sail Chicago offers a $100 rebate on joint/dual/household memberships to two members

    living at the same address. You can find instructions for obtaining a joint membership here.

    Reach out to membership@sailchicago.org for any further questions.

  • Sail Chicago is a member-run organization and is very similar to a co-op where the members are the owners and share in the roles and responsibilities of the organization. Here at Sail Chicago our members exercise their “owner’s responsibility” via an annual service requirement.

    Members are expected to sign up for jobs that contribute to running Sail Chicago each year. This is referred to as the “Member Service Requirement.” Members may choose to instead pay a $400 Opt-out fee, which is due at the beginning of the following sailing season.

    1. All new (first time) members are exempt from service during their first summer of membership only.

    2. In each subsequent year, returning members must sign up for one or more roles that will fulfill their annual Member Service Requirement of a minimum of 25 hours.

    3. If a member does not complete their Member Service Requirement during a season, they will be required to pay the Opt-Out Fee at the beginning of the next season in order to remain a member in good standing. The Opt-Out Fee reimburses Sail Chicago for the member not completing the Member Service Requirement for the previous year. It does not satisfy the current year's Member Service Requirement.

    Example: Member joins Sail Chicago for the 2013 season. No service time is required their first year. In 2014, they commit to serving on a boat maintenance team by the beginning of the sailing season, and then do actually participate as a boat team member, which satisfies their Member Service Requirement for 2014. In 2015, they sign up for a boat team but never actually participate, so they have not met their Member Service Requirement. They must pay the $400 Opt-Out Fee by the beginning of the 2016 season to cover the 2015 season.

  • We are a non-profit, member-run organization, which allows us to keep membership and boat usage fees at a low level. We offer a full array of courses taught by Sail Chicago members. Once sailors complete our skipper training course and pass a written test, they are qualified to have access to our boats for private use. After the first year of membership, we require our members to complete a minimum of 25 hours of service a year or to pay an opt out fee of $400. For details on all our classes, policies and how to become a member see sailchicago.org.