Your total trip with all stops is around 2,180 miles / 3510 km, taking roughly 33 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 Springfield, OR and Milwaukee, WI.
Start from Springfield, Oregon.
Spokane, Washington is stopping point #1 after driving about 460 miles (750 km) or 7.5 hours.
Billings, Montana is stopping point #2 after driving about 540 miles (870 km) or 8 hours. Your total trip so far is about 1,000 miles or 1610 km over roughly 15.5 hours of driving.
Dickinson, North Dakota is stopping point #3 after driving about 320 miles (510 km) or 4.5 hours. Your total trip so far is about 1,320 miles or 2120 km over roughly 20 hours of driving.
Fargo, North Dakota is stopping point #4 after driving about 290 miles (470 km) or 4 hours. Your total trip so far is about 1,610 miles or 2590 km over roughly 24.5 hours of driving.
Minneapolis, Minnesota is stopping point #5 after driving about 240 miles (380 km) or 3.5 hours. Your total trip so far is about 1,850 miles or 2970 km over roughly 28 hours of driving.
Finally, Milwaukee, Wisconsin is your destination after driving about 340 miles (540 km) or 5 hours. Your total trip with all stops is around 2,180 miles or 3510 km, taking roughly 33 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.