Your total trip with all stops is around 980 miles / 1580 km, taking roughly 16 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 BDL and ORD.
Start from Bradley International Airport.
Yonkers, New York is stopping point #1 after driving about 120 miles (190 km) or 2 hours.
Williamsport, Pennsylvania is stopping point #2 after driving about 200 miles (320 km) or 3.5 hours. Your total trip so far is about 310 miles or 500 km over roughly 5.5 hours of driving.
Cleveland, Ohio is stopping point #3 after driving about 290 miles (460 km) or 4.5 hours. Your total trip so far is about 600 miles or 970 km over roughly 10 hours of driving.
Toledo, Ohio is stopping point #4 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 720 miles or 1150 km over roughly 11.5 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 980 miles or 1580 km, taking roughly 16 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.