Stopping points from Washington Dulles International Airport to Chicago O'Hare International Airport:

• Start from Washington Dulles International Airport
• 4 hours to Pittsburgh, Pennsylvania after driving about 240 miles / 380 km
• 2 hours to Cleveland, Ohio after driving about 130 miles / 220 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 750 miles / 1210 km, taking roughly 12.5 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 IAD and ORD.

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Stopping points from IAD to ORD

Start from Washington Dulles International Airport.

Pittsburgh, Pennsylvania is stopping point #1 after driving about 240 miles (380 km) or 4 hours.

Cleveland, Ohio is stopping point #2 after driving about 130 miles (220 km) or 2 hours. Your total trip so far is about 370 miles or 600 km over roughly 6 hours of driving.

Toledo, Ohio is stopping point #3 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 490 miles or 790 km over roughly 8 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 750 miles or 1210 km, taking roughly 12.5 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.