Your total trip with all stops is around 2,130 miles / 3420 km, taking roughly 32 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 PDX.
Start from Chicago O'Hare International Airport.
Des Moines, Iowa is stopping point #1 after driving about 330 miles (530 km) or 5.5 hours.
Cheyenne, Wyoming is stopping point #2 after driving about 630 miles (1010 km) or 9 hours. Your total trip so far is about 960 miles or 1540 km over roughly 14.5 hours of driving.
Rock Springs, Wyoming is stopping point #3 after driving about 260 miles (410 km) or 3.5 hours. Your total trip so far is about 1,220 miles or 1960 km over roughly 18 hours of driving.
Ogden, Utah is stopping point #4 after driving about 180 miles (280 km) or 2.5 hours. Your total trip so far is about 1,390 miles or 2240 km over roughly 20.5 hours of driving.
Boise, Idaho is stopping point #5 after driving about 310 miles (490 km) or 4.5 hours. Your total trip so far is about 1,700 miles or 2730 km over roughly 25 hours of driving.
Finally, Portland International Airport is your destination after driving about 430 miles (690 km) or 7 hours. Your total trip with all stops is around 2,130 miles or 3420 km, taking roughly 32 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.