Your total trip with all stops is around 1,780 miles / 2860 km, taking roughly 26 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 TUS and MDW.
Start from Tucson International Airport.
Albuquerque, New Mexico is stopping point #1 after driving about 440 miles (710 km) or 6.5 hours.
Oklahoma City, Oklahoma is stopping point #2 after driving about 540 miles (880 km) or 8 hours. Your total trip so far is about 990 miles or 1590 km over roughly 14.5 hours of driving.
Saint Louis, Missouri is stopping point #3 after driving about 500 miles (800 km) or 7.5 hours. Your total trip so far is about 1,490 miles or 2390 km over roughly 21.5 hours of driving.
Finally, Chicago Midway International Airport is your destination after driving about 290 miles (470 km) or 4.5 hours. Your total trip with all stops is around 1,780 miles or 2860 km, taking roughly 26 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.