Stopping points from Winnipeg James Armstrong Richardson International Airport to Chicago, Illinois:

• Start from Winnipeg James Armstrong Richardson International Airport
• 4 hours to Fargo, North Dakota after driving about 230 miles / 360 km
• 3.5 hours to Minneapolis, Minnesota after driving about 240 miles / 380 km
• 4 hours to Madison, Wisconsin after driving about 270 miles / 430 km
• 2.5 hours to Chicago, Illinois after driving about 150 miles / 240 km

Your total trip with all stops is around 880 miles / 1410 km, taking roughly 14 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 YWG and Chicago, IL.

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Stopping points from YWG to Chicago, IL

Start from Winnipeg James Armstrong Richardson International Airport.

Fargo, North Dakota is stopping point #1 after driving about 230 miles (360 km) or 4 hours.

Minneapolis, Minnesota is stopping point #2 after driving about 240 miles (380 km) or 3.5 hours. Your total trip so far is about 460 miles or 740 km over roughly 7.5 hours of driving.

Madison, Wisconsin is stopping point #3 after driving about 270 miles (430 km) or 4 hours. Your total trip so far is about 730 miles or 1180 km over roughly 11.5 hours of driving.

Finally, Chicago, Illinois is your destination after driving about 150 miles (240 km) or 2.5 hours. Your total trip with all stops is around 880 miles or 1410 km, taking roughly 14 hours for the whole trip.

Stopping point calculator

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.