Your total trip with all stops is around 700 miles / 1130 km, taking roughly 12 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 VWU and Chicago, IL.
Start from Waskish Municipal Airport.
Saint Paul, Minnesota is stopping point #1 after driving about 290 miles (470 km) or 5.5 hours.
Madison, Wisconsin is stopping point #2 after driving about 260 miles (420 km) or 4 hours. Your total trip so far is about 550 miles or 890 km over roughly 9.5 hours of driving.
Finally, Chicago, Illinois is your destination after driving about 150 miles (240 km) or 2.5 hours. Your total trip with all stops is around 700 miles or 1130 km, taking roughly 12 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.