10 Best Ski Spots Within Driving Distance of Chicago Here are our favorite places to hit the slopes near Chicago: Boyne Mountain Resort MI A winter wonderland with diverse slopes and f a m i l y -friendly vibes boyne mountain Cascade Mountain WI Just a short drive away offering great skiing and snowboarding options for all skill levels cascademountain Chestnut Mountain Resort IL A local gem with breathtaking views of the Mississippi River chestnutmtn Granite Peak WI An a d r e n a l i n e -pumping experience with the highest vertical drop in the Midwest granitepeakskiarea Devil s Head Resort WI Perfect for a weekend getaway with challenging slopes and cozy accommodations devilsheadresort Crystal Mountain MI A scenic escape offering fantastic skiing amidst stunning landscapes crystalmountainmi Wilmot Mountain WI Great for day trips offering skiing and snowboarding lessons for all ages wilmotmtn