Stopping points from Naperville, Illinois to Plymouth, Massachusetts:

• Start from Naperville, Illinois
• 4 hours to Toledo, Ohio after driving about 270 miles / 440 km
• 5 hours to Buffalo, New York after driving about 310 miles / 500 km
• 5.5 hours to Springfield, Massachusetts after driving about 380 miles / 600 km
• 2 hours to Plymouth, Massachusetts after driving about 120 miles / 200 km

Your total trip with all stops is around 1,080 miles / 1740 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 Naperville, IL and Plymouth, MA.

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Stopping points from Naperville, IL to Plymouth, MA

Start from Naperville, Illinois.

Toledo, Ohio is stopping point #1 after driving about 270 miles (440 km) or 4 hours.

Buffalo, New York is stopping point #2 after driving about 310 miles (500 km) or 5 hours. Your total trip so far is about 580 miles or 940 km over roughly 9 hours of driving.

Springfield, Massachusetts is stopping point #3 after driving about 380 miles (600 km) or 5.5 hours. Your total trip so far is about 960 miles or 1540 km over roughly 14.5 hours of driving.

Finally, Plymouth, Massachusetts is your destination after driving about 120 miles (200 km) or 2 hours. Your total trip with all stops is around 1,080 miles or 1740 km, taking roughly 16.5 hours for the whole trip.

Stopping point calculator

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.