Chicago Area Riding Group
Just an FYI. There is an existing riding group sponsored by Jim Potts Spyder dealership in Woodstock. They have a few dozen members from what I've seen and sponsor a nice mix of rides. My wife and I haven't been very active with them but we've been to some of the organizing meetings, lunches, and one ride. While it sounds like a long way to go for the 3 of you who have posted above, I've met people from downtown Chicago and Wheaton. Their old website is woodstockspyderryders.com (the site support was discontinued last month because they moved all contact info to facebook which I don't use). However you can still see a sampling of their rides from the last couple years on the website. Hope you find or can develop something that can work for you.