Your total trip with all stops is around 1,050 miles / 1690 km, taking roughly 17 hours for the whole trip. If you want to see every small town along the way, you can get a full list of cities between Hampton, VA and Madison, WI.
Start from Hampton, Virginia.
Centreville, Virginia is stopping point #1 after driving about 170 miles (280 km) or 3 hours.
Pittsburgh, Pennsylvania is stopping point #2 after driving about 250 miles (410 km) or 4 hours. Your total trip so far is about 420 miles or 680 km over roughly 7 hours of driving.
Cleveland, Ohio is stopping point #3 after driving about 130 miles (220 km) or 2 hours. Your total trip so far is about 560 miles or 900 km over roughly 9 hours of driving.
Chicago, Illinois is stopping point #4 after driving about 340 miles (550 km) or 5.5 hours. Your total trip so far is about 900 miles or 1450 km over roughly 14.5 hours of driving.
Finally, Madison, Wisconsin is your destination after driving about 150 miles (240 km) or 2.5 hours. Your total trip with all stops is around 1,050 miles or 1690 km, taking roughly 17 hours for the whole trip.
Travelmath helps you figure out where to stop when planning a long road trip from one location to another. The best stopping point for an overnight hotel stay or a break from driving often depends on how far or how long you want to drive before pausing to rest. You can find the closest city to your stopping point to look for hotels, or explore other cities and towns along the route. Use this as a road trip planner when you're driving cross-country or mapping a route with multiple stops.