Your total trip with all stops is around 980 miles / 1580 km, taking roughly 16 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 MKE and HVN.
Start from General Mitchell International Airport.
South Bend, Indiana is stopping point #1 after driving about 180 miles (290 km) or 3 hours.
Cleveland, Ohio is stopping point #2 after driving about 260 miles (410 km) or 4 hours. Your total trip so far is about 440 miles or 700 km over roughly 7 hours of driving.
Newark, New Jersey is stopping point #3 after driving about 450 miles (730 km) or 7 hours. Your total trip so far is about 890 miles or 1430 km over roughly 14 hours of driving.
Finally, Tweed New Haven Regional Airport is your destination after driving about 90 miles (150 km) or 2 hours. Your total trip with all stops is around 980 miles or 1580 km, taking roughly 16 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.