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 PSM and MKE.
Start from Portsmouth International Airport at Pease.
Rochester, New York is stopping point #1 after driving about 440 miles (710 km) or 7.5 hours.
Cleveland, Ohio is stopping point #2 after driving about 260 miles (420 km) or 4 hours. Your total trip so far is about 700 miles or 1130 km over roughly 11.5 hours of driving.
Chicago, Illinois is stopping point #3 after driving about 340 miles (550 km) or 5.5 hours. Your total trip so far is about 1,050 miles or 1680 km over roughly 16.5 hours of driving.
Finally, General Mitchell International Airport is your destination after driving about 90 miles (140 km) or 1.5 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.