Your total trip with all stops is around 2,090 miles / 3360 km, taking roughly 31 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 SAN and ORD.
Start from San Diego International Airport.
Las Vegas, Nevada is stopping point #1 after driving about 330 miles (540 km) or 5 hours.
Grand Junction, Colorado is stopping point #2 after driving about 510 miles (810 km) or 7.5 hours. Your total trip so far is about 840 miles or 1350 km over roughly 12 hours of driving.
Denver, Colorado is stopping point #3 after driving about 240 miles (390 km) or 4 hours. Your total trip so far is about 1,080 miles or 1740 km over roughly 16 hours of driving.
Omaha, Nebraska is stopping point #4 after driving about 540 miles (870 km) or 7.5 hours. Your total trip so far is about 1,620 miles or 2610 km over roughly 23.5 hours of driving.
Finally, Chicago O'Hare International Airport is your destination after driving about 470 miles (750 km) or 7.5 hours. Your total trip with all stops is around 2,090 miles or 3360 km, taking roughly 31 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.