Your total trip with all stops is around 1,240 miles / 1990 km, taking roughly 18.5 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 Jacksonville, FL and Oshkosh, WI.
Start from Jacksonville, Florida.
Atlanta, Georgia is stopping point #1 after driving about 350 miles (560 km) or 5 hours.
Louisville, Kentucky is stopping point #2 after driving about 420 miles (680 km) or 6 hours. Your total trip so far is about 770 miles or 1230 km over roughly 11 hours of driving.
Chicago, Illinois is stopping point #3 after driving about 300 miles (480 km) or 4.5 hours. Your total trip so far is about 1,060 miles or 1710 km over roughly 16 hours of driving.
Finally, Oshkosh, Wisconsin is your destination after driving about 180 miles (280 km) or 3 hours. Your total trip with all stops is around 1,240 miles or 1990 km, taking roughly 18.5 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.