Your total trip with all stops is around 980 miles / 1580 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 ORD and BDL.
Start from Chicago O'Hare International Airport.
Toledo, Ohio is stopping point #1 after driving about 260 miles (420 km) or 4.5 hours.
Cleveland, Ohio is stopping point #2 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 380 miles or 610 km over roughly 6 hours of driving.
State College, Pennsylvania is stopping point #3 after driving about 240 miles (390 km) or 4 hours. Your total trip so far is about 620 miles or 1000 km over roughly 10.5 hours of driving.
Yonkers, New York is stopping point #4 after driving about 250 miles (400 km) or 4 hours. Your total trip so far is about 870 miles or 1400 km over roughly 14.5 hours of driving.
Finally, Bradley International Airport is your destination after driving about 110 miles (180 km) or 2.5 hours. Your total trip with all stops is around 980 miles or 1580 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.