Hi Vic,
Welcome! I will start with - should've found a project somewhere else ;). Seriously. No much carving in IL. 10% more in the surrounding Wisconsin, Indiana and Michigan. Probably further North - Minnesotta is better, but the drive from here (Chicago) would make it not worth (better spent that time driving to Colorado).
Local season is likely going to be over very soon.
Otherwise, from closer to Chicago to further away:
- Alpine Valley/Wilmot (WI) - ~1-1.5 hrs drive. Almost man made hills
- Cascade/Devil's Head (WI) - ~3-3.5 hrs drive. Just a bit longer, but more than half of the length is flat.
- Granite Peak (WI) - ~4.5 hrs drive, a bit longer than above and that's about as far as I personally drive for local trip ;). January - brutally cold, Russia type cold :)
- Boyne (MI) and around resorts - 6-8 hrs drive from Chicago. Never been there though.
If you have any other questions about stuff around, let me know.
Millen