Hey Mama!
I'm in Rockford, not far. Usually sail Sparky at Pierce Lake at Rock Cut State Park. Had a memorable trip on her camping in the Apostle Islands on Lake Superior last year with Matt of "Adventures In Reach". I'd be happy to bring her in to Chicago for a flotilla, maybe to Wilmette beach?
I occasionally come to Chicago with my Hobie Cat to sail from Burnham Harbor, but usually sail that boat on one of the Madison WI lakes.