Your total trip with all stops is around 1,070 miles / 1720 km, taking roughly 17.5 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 Wisconsin and Delaware.
Start from Wisconsin (WI).
Chicago, Illinois is stopping point #1 after driving about 230 miles (370 km) or 3.5 hours.
Toledo, Ohio is stopping point #2 after driving about 250 miles (390 km) or 4 hours. Your total trip so far is about 480 miles or 770 km over roughly 7.5 hours of driving.
Cleveland, Ohio is stopping point #3 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 590 miles or 960 km over roughly 9.5 hours of driving.
Frederick, Maryland is stopping point #4 after driving about 330 miles (530 km) or 5.5 hours. Your total trip so far is about 920 miles or 1490 km over roughly 15 hours of driving.
Finally, Delaware (DE) is your destination after driving about 140 miles (230 km) or 2.5 hours. Your total trip with all stops is around 1,070 miles or 1720 km, taking roughly 17.5 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.