Join Date: May 2010
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Not quite an answer to your direct question, but since you're apparently local to Chicago....
A few summers ago, I took lessons to learn the basics of keel boats at Hammond Marina. Price was right at $175 for 6 2-hour lessons'. I thought that the instruction was good, wish I could remember the instructor's name so I could give a recommendation. Also, in all the sailing I've done since, (up to most recently a 40' Beneteau in San Diego) I haven't run into anything that wasn't covered in those first lessons I took years ago. I'm still looking to get my ASA certs so I can charter or lease share on my own, but I'd say having those initial lessons under my belt, I'm pretty well prepared to breeze through the ASA classes/tests.
Also, if you're in Chicago over the summer, there's plenty of club race crews that are always looking for help. I'm not into racing, but I hear from sailing friends that it's a good way to learn a lot, and fast.