Stopping points from Chicago, Illinois to Windsor, Ontario:

• Start from Chicago, Illinois
• 2.5 hours to Kalamazoo, Michigan after driving about 150 miles / 230 km
• 2.5 hours to Windsor, Ontario after driving about 150 miles / 230 km

Your total trip with all stops is around 290 miles / 470 km, taking roughly 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 Chicago, IL and Windsor, Canada.

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• Chicago to Windsor drive
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Stopping points from Chicago, IL to Windsor, Canada

Start from Chicago, Illinois.

Kalamazoo, Michigan is stopping point #1 after driving about 150 miles (230 km) or 2.5 hours.

Finally, Windsor, Ontario is your destination after driving about 150 miles (230 km) or 2.5 hours. Your total trip with all stops is around 290 miles or 470 km, taking roughly 5 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.