Your total trip with all stops is around 1,100 miles / 1770 km, taking roughly 16.5 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 JAX and ORD.
Start from Jacksonville International Airport.
Macon, Georgia is stopping point #1 after driving about 280 miles (450 km) or 4 hours.
Murfreesboro, Tennessee is stopping point #2 after driving about 300 miles (480 km) or 4.5 hours. Your total trip so far is about 580 miles or 930 km over roughly 8.5 hours of driving.
Indianapolis, Indiana is stopping point #3 after driving about 320 miles (510 km) or 5 hours. Your total trip so far is about 900 miles or 1440 km over roughly 13.5 hours of driving.
Finally, Chicago O'Hare International Airport is your destination after driving about 210 miles (330 km) or 3 hours. Your total trip with all stops is around 1,100 miles or 1770 km, taking roughly 16.5 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.