How much should you expect to spend for a flight from Chicago Midway to Windsor?

Flight prices from Chicago to Windsor change depending on demand and time of booking.

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

Studies show that flying midweek — like on a Tuesday or Wednesday — can be cheaper than weekend flights. Still, airfares change frequently, so check updated prices on Jetcost.

Is there more than one airport in Chicago or Windsor?

Even short-haul routes can benefit from considering secondary airports. It may open up more flight times or cheaper fares.

• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.
• Airports in Windsor: Windsor is the only airport in operation.

Airports with more daily flights offer more flexibility if plans change or delays occur. If you’re flexible, consider airports near Windsor as well.

Smart ways to search flights from Chicago Midway 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, Halifax, Montreal, 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.