How much is a flight from Chicago to Windsor?

Prices vary based on date, airline, and availability. Compare several options if you're flying between Chicago and Windsor.

Pick a travel date to see today’s available fares.

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the Chicago - Windsor route.

Which airports serve Chicago and Windsor?

When planning a trip of about 393 km, it's a good idea to check flights from surrounding airports too.

• Airports in Chicago: Chicago is connected to 3 airports - Midway, O'Hare, Rockford.
• Airports in Windsor: The only active airport in Windsor is Windsor.

The closest airport isn’t always the cheapest — it’s worth checking the alternatives too. In some cities, smaller airports offer lower fares than the main ones.

Smart ways to search flights from Chicago to Windsor

Use Jetcost to view tailored results based on what you care about — time, duration, number of stops, or even your preferred booking agency. Results include the best airlines and travel agencies.

Other popular destinations

Flying to Canada? Other travelers also searched: Calgary, Montreal, Quebec, Toronto, Vancouver.

Prefer non-stop flights? Just activate the filter to skip unnecessary layovers. If your dates are flexible, you can also explore different departure and return combinations to find the best fit.