Have you come across ProductCamp Chicago? ProductCamps are fantastic events, and completely free. If you were looking for a local user group or community, you would find it there. http://www.pcampchicago.org/ (I am on the organizing team for ProductCamp Seattle).
Looks like they host in June - I would recommend contacting the organizing team? Also I would thoroughly recommend volunteering to help with their event - great fun and you will meet a ton of people!