Find out what a flight from Windsor to Chicago O'Hare might cost

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

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

Which departure and arrival airports are available?

Between Windsor and Chicago, flight options may depend on the combination of airports available.

• Airports in Windsor: Only Windsor is currently in operation.
• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Flight filters for the route Windsor – Chicago O'Hare

Customize your search on Jetcost to focus only on flights that suit your needs. Whether you want a direct connection, specific airline, or shorter layover, filters help you find it faster.

Other popular destinations

Flights to United States are often searched alongside: Las Vegas, Los Angeles, Miami, New York City, Orlando.

The cheapest flights might leave at odd hours or arrive at less central airports — keep that in mind. If you travel often, you can always select your trusted airlines from the available options.