Your total trip with all stops is around 1,010 miles / 1620 km, taking roughly 15 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 Milwaukee, WI and Cheyenne, WY.
Start from Milwaukee, Wisconsin.
Cedar Rapids, Iowa is stopping point #1 after driving about 250 miles (390 km) or 4 hours.
Des Moines, Iowa is stopping point #2 after driving about 130 miles (200 km) or 2 hours. Your total trip so far is about 370 miles or 600 km over roughly 6 hours of driving.
Omaha, Nebraska is stopping point #3 after driving about 140 miles (220 km) or 2 hours. Your total trip so far is about 510 miles or 820 km over roughly 8 hours of driving.
Kearney, Nebraska is stopping point #4 after driving about 190 miles (300 km) or 2.5 hours. Your total trip so far is about 690 miles or 1120 km over roughly 10.5 hours of driving.
Finally, Cheyenne, Wyoming is your destination after driving about 320 miles (510 km) or 4.5 hours. Your total trip with all stops is around 1,010 miles or 1620 km, taking roughly 15 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.