Strictly Sail is the highlight of the winter here in Chicago; lots of pretty things too look at, and even a few you might be able to afford!
Some yacht clubs have informal gatherings as they look for new members for the coming season, and very informal clubs like the Poor Mans Yacht Club typically will have bar nights.
The PMYC is a great way to meet other boaters in the area, talk about all things sailing, and is absurdly cheap
. 30$ per year or so....
You can meet them at strictly sail , and see if you want to join them for beers later.
With regards to working on a boat; I'll pay you in beer
Anyone in the yards can always use a hand. Meet people on forums
like this; or if you are bold you can always just show up. Try places like Canal Street, Crowleys, Chicago Yacht Yard, etc....
Welcome to the club!!