Looking for the price of a flight from Toronto Pearson to Chicago Midway?

There’s no fixed price — fares between Toronto 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.

Best airport options between Toronto and Chicago

If you're open to flying into or out of more than one airport, you’ll have more routes to compare.

• Airports in Toronto: Toronto is served by 4 airports - John C. Munro, Kitchener Lake, Lester B. Pearson, Toronto Island Airport.
• Airports in Chicago: In Chicago, 3 airports are available - Midway, O'Hare, Rockford.

Some airports offer extras like lounges, fast track, or self check-in — good to keep in mind. Comparing airports by services offered helps you balance cost and comfort.

Compare flights from Toronto Pearson to Chicago Midway with advanced filters

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Other popular destinations

Looking for alternatives in United States? Travelers also liked: Atlanta, Los Angeles, Miami, New York City, Orlando.

If you have a preferred time to leave or arrive, filters can help you show only the matching flights. You can also filter by your favorite airline and see only those deals.