Your total trip with all stops is around 500 miles / 800 km, taking roughly 8.5 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 JZK and Chicago, IL.
Start from Cloquet Carlton County.
Madison, Wisconsin is stopping point #1 after driving about 350 miles (560 km) or 6 hours.
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 500 miles or 800 km, taking roughly 8.5 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.