If you can stay near the I-94 corridor, your travel will be fairly easy, even to the employee parking lot.

Lake Geneva (great area).... you could use US Rt12 to IL53, to I-90... rt 12 traffic sucks, lots of lights. Other option is WI-50 east to I-94. less stressful, but might still be a longer ride.

For comparison, you can take I-90 west towards Rockford and get into WI... the IL/WI boarder is about 90 min to the lot there.

A lot of nice options near Madison too, but a longer drive. easy, but something you may not want to do more than once a week. about a 2:15hr drive if memory is good.