Your total trip with all stops is around 770 miles / 1240 km, taking roughly 12.5 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 Lake in the Hills, IL and Elkridge, MD.
Start from Lake in the Hills, Illinois.
South Bend, Indiana is stopping point #1 after driving about 140 miles (220 km) or 2.5 hours.
Cleveland, Ohio is stopping point #2 after driving about 260 miles (410 km) or 4 hours. Your total trip so far is about 390 miles or 630 km over roughly 6 hours of driving.
Pittsburgh, Pennsylvania is stopping point #3 after driving about 140 miles (220 km) or 2 hours. Your total trip so far is about 530 miles or 850 km over roughly 8.5 hours of driving.
Finally, Elkridge, Maryland is your destination after driving about 250 miles (390 km) or 4.5 hours. Your total trip with all stops is around 770 miles or 1240 km, taking roughly 12.5 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.