Looking for the price of a flight from Windsor to Chicago O'Hare?

There’s no fixed price — fares between Windsor and Chicago can vary a lot by day or time.

Select your dates to check current offers.

It’s often useful to check whether nearby airports offer better fares. Flying during less crowded periods also increases your chances of finding good deals.

Which airports serve Windsor and Chicago?

When planning a trip of about 254 mi, it's a good idea to check flights from surrounding airports too.

• Airports in Windsor: Windsor is the only operational airport in the area.
• Airports in Chicago: Chicago offers flights from 3 airports - Midway, O'Hare, Rockford.

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.

Adjust your flight filters for Windsor – Chicago O'Hare

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 United States? These cities are popular too: Las Vegas, Los Angeles, Miami, New York City, Orlando.

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.