The skiing in the area is definitely small. It's enough to keep me happy, getting my skiing fix a few nights a week, but it's definitely a whole different ballgame from mountains. Like Shredhead said, there's plenty of great stuff to pack into visits if you're not particularly looking to ski. If you are looking to get some Midwestern skiing in, here are my two personal favorites.Cascade
is three hours away, and if you and him want to ski together and are up for a day trip or overnighter. They've got a high speed quad and longer runs than places closer to Chicago. As a Chicago dweller, it's a good place to head on weekends.Wilmot
is much smaller and old fashioned. It's the kind of place that's described either as nostalgic or dilapidated, depending on the person talking about it. The lifts are slow, the snow is icy, but it's close and stays open til 11 pm. It makes it easy to get on the snow a few nights a week after work.
If you want more places or links for skiing around here or general Chicago info, feel free to ask.