Your total trip with all stops is around 1,030 miles / 1650 km, taking roughly 16.5 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 Virginia Beach, VA and Milwaukee, WI.
Start from Virginia Beach, Virginia.
Pittsburgh, Pennsylvania is stopping point #1 after driving about 440 miles (710 km) or 7 hours.
Cleveland, Ohio is stopping point #2 after driving about 140 miles (230 km) or 2.5 hours. Your total trip so far is about 580 miles or 940 km over roughly 9 hours of driving.
South Bend, Indiana is stopping point #3 after driving about 260 miles (410 km) or 4 hours. Your total trip so far is about 840 miles or 1350 km over roughly 13.5 hours of driving.
Finally, Milwaukee, Wisconsin is your destination after driving about 190 miles (300 km) or 3 hours. Your total trip with all stops is around 1,030 miles or 1650 km, taking roughly 16.5 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.