Your total trip with all stops is around 730 miles / 1170 km, taking roughly 11.5 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 YYC and DIK.
Start from Calgary International Airport.
Medicine Hat, Canada is stopping point #1 after driving about 180 miles (290 km) or 3 hours.
Havre, Montana is stopping point #2 after driving about 130 miles (220 km) or 2.5 hours. Your total trip so far is about 320 miles or 510 km over roughly 5 hours of driving.
Glendive, Montana is stopping point #3 after driving about 310 miles (500 km) or 5 hours. Your total trip so far is about 630 miles or 1010 km over roughly 10 hours of driving.
Finally, Dickinson Theodore Roosevelt Regional Airport is your destination after driving about 110 miles (170 km) or 1.5 hours. Your total trip with all stops is around 730 miles or 1170 km, taking roughly 11.5 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.