Find out what a flight from Chicago to Windsor might cost

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

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.

Planning flights between Chicago and Windsor? Don’t forget the airport options

Especially when flying to medium or large cities, it's worth checking all possible airport combinations before booking.

• Airports in Chicago: 3 airports are listed in Chicago - Midway, O'Hare, Rockford.
• Airports in Windsor: Only Windsor is currently available.

Check for differences in transport costs to and from each airport — they affect your total spend. Choosing the right airport can make a real difference in price and timing.

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.