Here's the 2nd closest ski resort from Chicago, and it's worth the extra driving up from/passing the Wilmot (25-30 mins). I kind of like black runs, but too short. Blue and Green runs are overcrowded all the time.
The bridge leading to a lift chair (from black/blue runs on West side) serioulsy needs expansion. It's too narrow to cross. I saw some skiers and boarders ended up falling into water.