Learning in Chicago?
I don''t think you are going to beat the Racine deal in very many places. One other option, although certainly more expensive and a different experience, is ASA classes. Search American Sailing Association and you should find many places in the Midwest. This can be a live aboard 4 day weekend, a close to home class, or the later classes can be a week on the boat. I believe that there are a couple places in Chicago and Waukegan as well as Wisconsin and Michigan Lake Michigan experiences or Apostle Islands experiences.