I don't know if this makes much sense. To get from Chicago to SLC is about a ~3 hour flight. You have to get to the airport about 1 hour before your flight time. It'll take you an additional hour to get off the plane, get luggage and rental car. Then it'll take about 45 minutes to get to a resort. That's almost 6 hours to get to one fo the SLC area resorts which are probably the most accessible major resorts in the US. In addition, flying out west incurs significant additional expense ($250+ airfare, rental car, increased cost of housing, increased cost of lift tickets, etc).
Lastly, Bohemia is an 8 hour drive from Madison, FIB Town is 2 1/2 hours south, how could it take 7 hours to get there. How can you people tell him these drive times; Lutsen 8 hours??? Ya, if your on the Auto Bond.
Mt. Bohemia is probably 9.5 hours from Chicago. To get to Lutsen is around 10 hours. This is assuming good driving conditions.
You will get bored of Chestnut after 1 ski day. But, you'll get bored of all the ski areas within 5 hour drive of Chicago after a day except for Granite Peak. However, most of these areas have another resorts close by which you can ski for a 2nd day. You can do Chestnut and Sundown Mtn (in Iowa about 45 minutes away) together or Cascade and Devil's Head together.
I agree that going to Wilmot is worth a couple of times a season. I'd definitely avoid it during the weekends. Very crowded with lots of out of control skiers and boarders. If you can go during a weekday it's much more manageable. If it isn't too cold, getting up to Wilmot for night skiing can be fun. BTW, you can ski at night a almost all Midwest resorts.