We have just announced a Vintage tournament in Chicago proper for Saturday November 18. All details here: https://www.facebook.com/events/146845216065567/
We're probably going to work with a couple of local venues to do start doing regular monthly Vintage tournaments in Chicago (some will be at game stores, some will be at bars and/or breweries). I'm thinking about organizing a quarterly event in Milwaukee as well. If you are interested in playtesting we now have a group of about a dozen guys in the Chicago proper for Vintage, as well as a handful more in the surrounding suburbs. Feel free to DM me if interested.