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Where can I park? 

If you're looking for parking close to the Sail Chicago dock meeting point, 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 meeting dock. 

If you're renting 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. 

Where do Sail Chicago classes meet? 

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. 

What will I learn in each class? Can I see a curriculum? 

To help you get an idea of what skills are taught in each course, read the provided course descriptions. If you'd like more information about exactly which skills are taught, you can read the syllabus for each of our Basic, Intermediate and Advanced sailing courses here. 

What are the benefits of membership? 

Membership benefits include: discounted Sail Chicago (US Sailing-certified*) instruction classes, access to free sailing opportunities through Tiller Time and Member Cruise Outings, numerous social events throughout the year, a chance to provide sailing opportunities for disadvantaged children in the Chicago area, a strong community of enthusiastic sailors, and access to a fleet with a variety of well-maintained boats.


When does annual membership begin and end?

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.  


Do you offer dual membership or household membership? 

Yes, dual membership is available to people living at the same address.  The cost for a dual membership is currently $300.  You may sign up on


What is the cancellation policy for Sail Chicago classes and membership?

Our cancellation policy can be found at


What are the service requirements? Do I need to complete them in my first year? 

Sail Chicago has been an all volunteer organization since the beginning. So we require members to contribute via an annual service requirement. New members are exempt from this requirement during their first sailing season. Service requirements are an average of 20 hours of service, and must be met by the start of the current sailing season. For example, you can complete your service requirement between May 2015 and May 2016, for the 2016 sailing season. Service positions range from administrative tasks to boat maintenance and outboard engine repair to skippering Tiller Times, to instructing a class.

Contact Chris Garvey,, for more information on available jobs. 


What is the fleet like? How easy is it to reserve boats? How much does it cost? 

Our fleet consists of (2) Ideal 18s, (2) Rhodes 19s, (7) Colgate 26s, and (2) cruising boats, an '84 Hunter 34 and a '94 Ericson 34.  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 can be found on the membership page.


I already know how to sail. Do I need to take Skipper training? How do I qualify as a skipper? 

In order to become a Sail Chicago skipper, a member must take the four-session Advanced/Skipper-Prep course. Successful completion of the course and course tests will qualify you as a Sail Chicago skipper and enable you to take out Sail Chicago boats as well as makes you eligible to obtain U.S. Sailing Basic Keelboat certification. NOTE: Private boat use is granted based on an instructor's evaluation of your skills. For 12 months following your skipper certification, you will be required to sail with another Sail Chicago skipper on board. 


How many Tiller Times/ Member Cruise Outings will I be able to attend? How frequently are they scheduled? 

You may sign up for a maximum of (2) Tiller Times at a time.  Once you've completed these, you may sign up for (2) more Tiller Times. As Member Cruise Outings become available during the sailing season, you may sign up for as many as you like.  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.

Do you offer classes off site? 

Currently we do not offer classes in locations other than Monroe and Belmont Harbors (cruising only). 

What are your classes like? What can I expect to master in each level? 

On-the-water classes consist of a maximum of 4 students.  We have three levels of classes:  Basic, Intermediate, and Skipper Prep. In addition, we offer more advanced classes in single-handed sailing, spinnaker, racing, and cruising.  For more information, visit the Learn page on and click through classes to read more about course curriculum. 


If I take a class as a non-member, can I upgrade to full membership afterward? 

Of course! If you decide that you'd like to be a Sail Chicago member after your class, you can pay the $125 upgrade fee.