There have been Pd user groups in Chicago in the past. One used to meet at Deadtech, but I think Rob Ray is currently at RPI. Before that there was a Max user group that also encompassed Pd and SuperCollider which I helped start out many years ago ('98 or so).
You may want to contact the Chicago New Media google group: http://groups.google.com/group/Chicago-new-media?lnk=srg&ie=UTF-8&oe=utf-8&pli=1
Also, look up Drew Browning at UIC and Robb Drinkwater at SAIC who are into such things. Paul Hertz is up at Northwestern, and there might be someone at U of Chicago too.