We live about 1/2 hour north of Milwaukee, although we have never driven to Disney, we did just return from a driving trip to Stone Mountain, GA. It took us about 14 hours and we did it all in 1 day. Friends of ours live near Stone Mountain, and they drive to Disney every year it takes around 8 hours. So I guess it would be around 23 or 24 hours for you. I think that would definately require an overnight stop. We decided we would never drive to Disney because we were pretty worn out after driving 14 hours. Midwest Express has really reasonable airfare out of Milwaukee, and that is our favorite airline. Sorry, I can't help you with the route. I know we went through IL, IN, KY, & TN, but am not sure of all the highways.