Your total trip with all stops is around 820 miles / 1320 km, taking roughly 13.5 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 YPG and Calgary, Canada.
Start from Portage la Prairie/Southport Airport.
Weyburn, Canada is stopping point #1 after driving about 480 km (300 miles) or 5 hours.
Medicine Hat, Canada is stopping point #2 after driving about 540 km (340 miles) or 5.5 hours. Your total trip so far is about 1030 km or 640 miles over roughly 10.5 hours of driving.
Finally, Calgary, Alberta is your destination after driving about 290 km (180 miles) or 3 hours. Your total trip with all stops is around 1320 km or 820 miles, taking roughly 13.5 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.