Stopping points from Portland International Jetport to Chicago O'Hare International Airport:

• Start from Portland International Jetport
• 6 hours to Syracuse, New York after driving about 410 miles / 660 km
• 2.5 hours to Buffalo, New York after driving about 150 miles / 240 km
• 3.5 hours to Cleveland, Ohio after driving about 190 miles / 310 km
• 2 hours to Toledo, Ohio after driving about 120 miles / 190 km
• 4.5 hours to Chicago O'Hare International Airport after driving about 260 miles / 420 km

Your total trip with all stops is around 1,130 miles / 1810 km, taking roughly 18 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 PWM and ORD.

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Stopping points from PWM to ORD

Start from Portland International Jetport.

Syracuse, New York is stopping point #1 after driving about 410 miles (660 km) or 6 hours.

Buffalo, New York is stopping point #2 after driving about 150 miles (240 km) or 2.5 hours. Your total trip so far is about 560 miles or 900 km over roughly 8.5 hours of driving.

Cleveland, Ohio is stopping point #3 after driving about 190 miles (310 km) or 3.5 hours. Your total trip so far is about 750 miles or 1200 km over roughly 11.5 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 860 miles or 1390 km over roughly 13.5 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 1,130 miles or 1810 km, taking roughly 18 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.