Your total trip with all stops is around 1,130 miles / 1820 km, taking roughly 18 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 Chesapeake, VA and Appleton, WI.
Start from Chesapeake, Virginia.
Centreville, Virginia is stopping point #1 after driving about 200 miles (330 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 460 miles or 730 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 590 miles or 950 km over roughly 9.5 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 930 miles or 1500 km over roughly 15 hours of driving.
Finally, Appleton, Wisconsin is your destination after driving about 200 miles (310 km) or 3 hours. Your total trip with all stops is around 1,130 miles or 1820 km, taking roughly 18 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.