Your total trip with all stops is around 930 miles / 1490 km, taking roughly 14.5 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 Olive Branch, MS and Midland, MI.
Start from Olive Branch, Mississippi.
Cape Girardeau, Missouri is stopping point #1 after driving about 190 miles (310 km) or 3 hours.
Decatur, Illinois is stopping point #2 after driving about 250 miles (410 km) or 4 hours. Your total trip so far is about 450 miles or 720 km over roughly 7.5 hours of driving.
Chicago, Illinois is stopping point #3 after driving about 180 miles (290 km) or 3 hours. Your total trip so far is about 630 miles or 1010 km over roughly 10 hours of driving.
Finally, Midland, Michigan is your destination after driving about 300 miles (480 km) or 4.5 hours. Your total trip with all stops is around 930 miles or 1490 km, taking roughly 14.5 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.