Your total trip with all stops is around 810 miles / 1300 km, taking roughly 13 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 Pine Bluff, AR and Milwaukee, WI.
Start from Pine Bluff, Arkansas.
Memphis, Tennessee is stopping point #1 after driving about 140 miles (230 km) or 2.5 hours.
Paducah, Kentucky is stopping point #2 after driving about 200 miles (320 km) or 3 hours. Your total trip so far is about 340 miles or 550 km over roughly 6 hours of driving.
Chicago, Illinois is stopping point #3 after driving about 370 miles (600 km) or 5.5 hours. Your total trip so far is about 720 miles or 1150 km over roughly 11.5 hours of driving.
Finally, Milwaukee, Wisconsin is your destination after driving about 90 miles (150 km) or 1.5 hours. Your total trip with all stops is around 810 miles or 1300 km, taking roughly 13 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.