Your total trip with all stops is around 1,350 miles / 2160 km, taking roughly 22.5 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 YCR and Chicago, IL.
Start from Cross Lake Airport.
Winnipeg, Canada is stopping point #1 after driving about 480 miles (770 km) or 9.5 hours.
Minneapolis, Minnesota is stopping point #2 after driving about 460 miles (730 km) or 7 hours. Your total trip so far is about 940 miles or 1510 km over roughly 16.5 hours of driving.
Finally, Chicago, Illinois is your destination after driving about 410 miles (660 km) or 6 hours. Your total trip with all stops is around 1,350 miles or 2160 km, taking roughly 22.5 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.