This burg, where the prairie meets the Great Lakes, could scarcely be flatter. Nonetheless, Chicago isn't too shabby a place to be a skier or snowboarder. O'Hare has flights to all the major ski resorts out West, and there are many chairlifts in Chicago's vacation paradise: Wisconsin. Glaciers carved some fairly nice ski mountains on the other side of the lake, too, in Michigan.
No one would ever confuse tiny Wilmot with a ski resort in the Rockies or Appalachians, but it has promised Chicagoans reliable turns since 1952, when it pioneered the making of artificial snow. Wilmot offers lessons, racing, night skiing and snow tubing for those who want to slide with their posterior closer to the ground. The ultimate day-ski area, it promises "Family Fun is only a short drive away!"
The glacier-formed Baraboo Bluffs area of central Wisconsin, with its beautiful woods and countless lakes, might be better known for summer recreation. Yet Chicagoans have road-tripped here for skiing and snowboarding forever, exulting over 30 runs spilling down a 500-foot vertical rise. Devil's Head is famed for its fantastic cruising on carpet-smooth slopes. Indeed, the resort grooms its cruisers twice a day. Keep an eye out for snowcats, then let it rip.