Hi Anne,
Skate or classical? Do you prefer groomed ski trails, or ungroomed hiking trails winding through the woods?
I like to take the South Shore over to Dune Park; a rustic ski trail starts two blocks from the station that winds through the National Lakeshore for miles. You can usually count on decent skied-in tracks so you're not breaking trail as you ski. Then you can catch the South Shore back to Illinois from the Beverly Shores station, so you get a point-to-point ski experience.
Then next month we're going up to Minocqua Winter Park for a couple of days to enjoy their meticulous grooming on their 70+km of ski trails. Lots of good snow, ski areas, instruction and ski shops in northern Wisconsin and the UP. I'd almost rather do ski vacations there than out West. But before I go I check current midwest ski conditions at the Skinny Ski website.
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