Your total trip with all stops is around 1,030 miles / 1660 km, taking roughly 17.5 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 Pawtucket, RI and Chicago, IL.
Start from Pawtucket, Rhode Island.
Yonkers, New York is stopping point #1 after driving about 170 miles (280 km) or 3.5 hours.
Wilkes-Barre, Pennsylvania is stopping point #2 after driving about 140 miles (220 km) or 2.5 hours. Your total trip so far is about 310 miles or 500 km over roughly 6 hours of driving.
Cleveland, Ohio is stopping point #3 after driving about 360 miles (580 km) or 6 hours. Your total trip so far is about 670 miles or 1080 km over roughly 12 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 780 miles or 1260 km over roughly 14 hours of driving.
Finally, Chicago, Illinois is your destination after driving about 250 miles (390 km) or 4 hours. Your total trip with all stops is around 1,030 miles or 1660 km, taking roughly 17.5 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.