Chestnut Mountain is the best ski resort I've come across in the Midwest, coming from Chicago. There are activities for all members of the family - skiing/snowboarding, nightlife, dining, game room, swimming, sauna, jacuzzi, spa. Their trails range from bunny to expert, a run for any skill level. "Far Side" terrain park. It's vertical drop is nearly twice as high as Wilmot. Galena, the town it's situated in, offers more than Merrimac, Wis. (Devil's Head). There is simply no better resort in the midwest/chicago area.
The only down-side is the couple of miles you travel on Blackjack Road. It can be pretty risky when snowing.