Your total trip with all stops is around 940 miles / 1520 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 Biloxi, MS and Chicago, IL.
Start from Biloxi, Mississippi.
Brandon, Mississippi is stopping point #1 after driving about 160 miles (260 km) or 3 hours.
Memphis, Tennessee is stopping point #2 after driving about 220 miles (360 km) or 3 hours. Your total trip so far is about 380 miles or 610 km over roughly 6.5 hours of driving.
Belleville, Illinois is stopping point #3 after driving about 270 miles (430 km) or 4.5 hours. Your total trip so far is about 650 miles or 1040 km over roughly 11 hours of driving.
Decatur, Illinois is stopping point #4 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 760 miles or 1230 km over roughly 13 hours of driving.
Finally, Chicago, Illinois is your destination after driving about 180 miles (290 km) or 3 hours. Your total trip with all stops is around 940 miles or 1520 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.