Oh I forgot, Sunburst is a little bit North of Milwaukee... I haven't been there personally but I know it trumps any mountain you'll find down near the IL/WI border. Check that place out, there might be a few around that area.
Hey bud, yeah my GF and I snowboard. We did a Devils Head pass last season. It was pretty good but we're doing Cascade this year since its bigger and offers more stuff. If you're at Parkside (right?) then I'd say Cascade/Devils Head is a bit of a hike for you (only about 35-45 min for me) so you should probably do Wilmot, Alpine Valley or Grand Geneva since those are all a lot closer to you. If you don't mind the drive (I'd figure about 2 1/2 hrs each way from Kenosha) then Cascade is where the action is at, plus its literally right off the highway. Hope that helps.