Hi Ash ...
You might get detailed, Chicago local, advice over at Anything Sailing - http://www.anything-sailing.com/
They have an active group of users that are based in the greater Chicago area and points around the south end of Lake Michigan.
Many of the suggestions about local Yacht Clubs in the Chicago area aren't for the social aspects. All of these clubs sponsor
full schedules of sailboat racing
during the season. Often these schedules include a "fun" race
series as well as a competitive series. Skippers are always looking for crew.
Our yacht club, in Milwaukee, sponsors a Crew Search event every Spring designed to bring people like you together with skippers in search of new sailors
. I understand your desire to take out friends `n family
but being a part of a race
crew provided valuable experience.
I learned the basics with the University of Wisconsin - Madison sailing club, gained experience racing with South Shore Yacht Club, eventual bought my own boat and then upgrade to the current family
cruiser. Still race
(crew) in Milwaukee aboard a `82 Pearson
Flyer and cruise
to Chicago. Official launch time arrives here at the end of the month.
Welcome to sailing!