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!
The PMC is a non-profit, volunteer driven organization for Product Management professionals. We are based in Seattle. We enable product managers to connect, share, participate and learn from each other. We host monthly events, an online community, job postings and ProductCamp Seattle.
The PMC hosts 10 monthly events every calendar year. Each event is priced at $25. Events are typically presentations on specific topics of interest to the Product Management community.
We offer an annual pass for $99, providing you access to all monthly events for one calendar year from purchase.