Your total trip with all stops is around 890 miles / 1430 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 JFK and ORD.
Start from John F. Kennedy International Airport.
Wilkes-Barre, Pennsylvania is stopping point #1 after driving about 150 miles (240 km) or 3 hours.
Cleveland, Ohio is stopping point #2 after driving about 360 miles (580 km) or 6 hours. Your total trip so far is about 510 miles or 820 km over roughly 9 hours of driving.
Toledo, Ohio is stopping point #3 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 620 miles or 1000 km over roughly 10.5 hours of driving.
Finally, Chicago O'Hare International Airport is your destination after driving about 260 miles (420 km) or 4.5 hours. Your total trip with all stops is around 890 miles or 1430 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.