What is the best Ski/Snowboard location nearby (Chicago)

Hi Guys,
my snowboard needs a ride and I do not want to fly all the way to Aspen or Breckenridge.
What is a cool location nearby
- for a weekend event
- within 5h max drive
- with challenging slopes
- a nice apres ski party

Btw:
Would anybody be interested in such a weekend event?
From my experience it is much more fun doing it in a group than doing it alone.