Your total trip with all stops is around 1,170 miles / 1870 km, taking roughly 18.5 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 Lowell, MA and Madison, WI.
Start from Lowell, Massachusetts.
Albany, New York is stopping point #1 after driving about 170 miles (280 km) or 3 hours.
Buffalo, New York is stopping point #2 after driving about 290 miles (470 km) or 4.5 hours. Your total trip so far is about 460 miles or 750 km over roughly 7.5 hours of driving.
Cleveland, Ohio is stopping point #3 after driving about 190 miles (310 km) or 3 hours. Your total trip so far is about 660 miles or 1060 km over roughly 10.5 hours of driving.
Toledo, Ohio is stopping point #4 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 770 miles or 1240 km over roughly 12 hours of driving.
Chicago, Illinois is stopping point #5 after driving about 250 miles (390 km) or 4 hours. Your total trip so far is about 1,020 miles or 1640 km over roughly 16 hours of driving.
Finally, Madison, Wisconsin is your destination after driving about 150 miles (240 km) or 2.5 hours. Your total trip with all stops is around 1,170 miles or 1870 km, taking roughly 18.5 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.