Stopping points from Chicago O'Hare International Airport to Boston Logan International Airport:

• Start from Chicago O'Hare International Airport
• 4.5 hours to Toledo, Ohio after driving about 260 miles / 420 km
• 5 hours to Buffalo, New York after driving about 310 miles / 500 km
• 2.5 hours to Syracuse, New York after driving about 150 miles / 250 km
• 5.5 hours to Boston Logan International Airport after driving about 320 miles / 510 km

Your total trip with all stops is around 1,040 miles / 1680 km, taking roughly 17 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 BOS.

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Stopping points from ORD to BOS

Start from Chicago O'Hare International Airport.

Toledo, Ohio is stopping point #1 after driving about 260 miles (420 km) or 4.5 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 570 miles or 920 km over roughly 9 hours of driving.

Syracuse, New York is stopping point #3 after driving about 150 miles (250 km) or 2.5 hours. Your total trip so far is about 730 miles or 1170 km over roughly 11.5 hours of driving.

Finally, Boston Logan International Airport is your destination after driving about 320 miles (510 km) or 5.5 hours. Your total trip with all stops is around 1,040 miles or 1680 km, taking roughly 17 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.