Ash, welcome to Chicago! I actually work for Chicago Sailing and want to give you a bit more information.
Depending on your experience, you may want to take our Refresher course as opposed to the Basic course. If you'd like, you can call the office and I can talk you through the steps. I'd also recommend taking our Advanced course and getting US SAILING certified.
In terms of some of the other suggestions, those are all awesome! We are not a traditional yacht club, you should visit Columbia
and Chicago Yacht Clubs and check out the racing
boards for crewing
spots. We work with a meetup group (meetup.com) called The Keel
Joys, they do a lot of social sailing on our boats and other boats. Craigslist is another great place to connect with other sailors.
is your thing, you should also check out the Chicago Match Race Center. We share our dock
with them and they have a really cool program!
There's tons more to tell you! Chicago is a fantastic city for sailing. We look forward to seeing you out there this season.