Your total trip with all stops is around 1,050 miles / 1680 km, taking roughly 16.5 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 CYS and MDW.
Start from Cheyenne Regional Airport.
North Platte, Nebraska is stopping point #1 after driving about 250 miles (410 km) or 4 hours.
Lincoln, Nebraska is stopping point #2 after driving about 230 miles (360 km) or 3.5 hours. Your total trip so far is about 480 miles or 770 km over roughly 7.5 hours of driving.
Cedar Rapids, Iowa is stopping point #3 after driving about 320 miles (510 km) or 5 hours. Your total trip so far is about 800 miles or 1280 km over roughly 12.5 hours of driving.
Finally, Chicago Midway International Airport is your destination after driving about 250 miles (400 km) or 4 hours. Your total trip with all stops is around 1,050 miles or 1680 km, taking roughly 16.5 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.