Your total trip with all stops is around 2,130 miles / 3430 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 PDX and ORD.
Start from Portland International Airport.
Boise, Idaho is stopping point #1 after driving about 430 miles (690 km) or 7 hours.
Ogden, Utah is stopping point #2 after driving about 310 miles (490 km) or 4.5 hours. Your total trip so far is about 730 miles or 1180 km over roughly 11.5 hours of driving.
Rock Springs, Wyoming is stopping point #3 after driving about 180 miles (290 km) or 2.5 hours. Your total trip so far is about 910 miles or 1470 km over roughly 14 hours of driving.
Cheyenne, Wyoming is stopping point #4 after driving about 260 miles (420 km) or 3.5 hours. Your total trip so far is about 1,170 miles or 1880 km over roughly 17.5 hours of driving.
Omaha, Nebraska is stopping point #5 after driving about 500 miles (800 km) or 7 hours. Your total trip so far is about 1,670 miles or 2680 km over roughly 24.5 hours of driving.
Finally, Chicago O'Hare International Airport is your destination after driving about 470 miles (750 km) or 7.5 hours. Your total trip with all stops is around 2,130 miles or 3430 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.