Your total trip with all stops is around 960 miles / 1550 km, taking roughly 15 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 Sumter, SC and Beloit, WI.
Start from Sumter, South Carolina.
Asheville, North Carolina is stopping point #1 after driving about 210 miles (340 km) or 3.5 hours.
Lexington-Fayette, Kentucky is stopping point #2 after driving about 280 miles (460 km) or 4.5 hours. Your total trip so far is about 500 miles or 800 km over roughly 7.5 hours of driving.
Indianapolis, Indiana is stopping point #3 after driving about 190 miles (300 km) or 3 hours. Your total trip so far is about 690 miles or 1100 km over roughly 10.5 hours of driving.
Chicago, Illinois is stopping point #4 after driving about 180 miles (290 km) or 3 hours. Your total trip so far is about 870 miles or 1400 km over roughly 13.5 hours of driving.
Finally, Beloit, Wisconsin is your destination after driving about 100 miles (160 km) or 1.5 hours. Your total trip with all stops is around 960 miles or 1550 km, taking roughly 15 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.