What is the best place to ski within a few hours of Chicago?
I'd say I am intermediate but am willing to travel
I grew up in Central Wisconsin and would say the best real mountain conditions and steep enough to have some fun is at Granite Peak (Formerly Rib Mtn) in Wausau, Wisconsin. http://skigranitepeak.com/ The drive is about 5-6 hours from Chicago.
If you have more time head north of Wausau about 2 more hours to the multiple ski resorts in Northern Michigan.
Wheels up to wheels down is about 2 hours to DEN, 2:15 to ASE, EGE, HDN or GUC. Montrose is slightly more and SLC a little over 3.
I don't ski in the midwest much.