I lived in Chicago when I was VERY young, 4-5 years old. All I do remember of Chicago was the cold.
Photos of me and my sister, taken during the snowy winters make us look like Pillsbury dough-girls!
Our winters have been pretty cushy over the last twenty five years or so. (index flow. love it) Swimming is doable (if you're Russian, or Irish, maybe). I do remember waist-deep snow on Easter morning, but my waist was much closer to the sidewalk then.
Sorry for the tardy response, but I don't login that much anymore.