Cheap flights from Chicago O'Hare to Windsor

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

There’s no fixed price — fares between Chicago and Windsor 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 Chicago and Windsor?

When planning a trip of about 409 km, it's a good idea to check flights from surrounding airports too.

  • Airports in Chicago: Chicago is connected to 3 airports - Midway, O'Hare, Rockford.
  • Airports in Windsor: The only active airport in Windsor is Windsor.

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 Chicago O'Hare – Windsor

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from the best travel agencies and carriers.

Other popular destinations

Planning a trip to Canada? These cities are popular too: Calgary, Montreal, Quebec, 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.
Frequently Asked Questions

Frequently asked questions about flights from Chicago O'Hare to Windsor.

How much does an airline ticket from Chicago O'Hare to Windsor cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Chicago O'Hare to Windsor.

How far is Chicago from Windsor?

Chicago is about 409 km from Windsor.

What are the airports in Windsor?

Windsor has one airport: Windsor.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in Canada?

The most popular cities in Canada according to our users' searches are: Calgary, Montreal, Quebec, Toronto, Vancouver.

When should I book a flight from Chicago to Windsor?

This information is not available at the moment.

What is the cheapest month to fly from Chicago to Windsor?

This information is not available at the moment.

What is the most expensive month to fly from Chicago to Windsor?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to Windsor?

This information is not available at the moment.