Find out what a flight from Chicago Midway 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.

Flying from or to Chicago and Windsor? Here are your airport options

Knowing your full list of nearby airports can make flight planning easier, especially when routes vary.

• Airports in Chicago: You have 3 departure options - Midway, O'Hare, Rockford.
• Airports in Windsor: Windsor is the only arrival option right now.

For families or those traveling with assistance, smaller airports can be easier to navigate. Cities served by multiple airports often allow for more flexible travel planning.

Adjust your flight filters for Chicago Midway – Windsor

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from agencies like Expedia, eDreams, and more.

Other popular destinations

Planning a trip to Canada? These cities are popular too: Calgary, Halifax, Montreal, Toronto, Vancouver.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.