Flights

Flights from Toronto to Chicago

Fares we've seen from Toronto (YYZ) to Chicago (ORD) start from US$139 on 14 Oct 2026 with Porter. Prices come from partner searches in the last 48 hours and change quickly, so look before you book.

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Compare Toronto to Chicago on your dates and see current fares from our sources, listed by price.

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Fares by month

Month	Seen from	Date	Airline
October 2026	US$139	14 Oct 2026	Porter · direct	Check now
November 2026	US$174	8 Nov 2026	United · direct	Check now
December 2026	US$237	31 Dec 2026	American Airlines · direct	Check now
January 2027	US$214	12 Jan 2027	Porter · 1 stop	Check now

One-way fares in US dollars, last seen on Aviasales. They can change at any time and may not be available on every day of the month. Partner links: we may earn a commission if you book, at no extra cost to you.

Airlines on this route

Airlines we've seen with fares on this route, listed by price:

Porter: from US$139 (direct)
United: from US$174 (direct)
Air Canada: from US$223 (direct)
American Airlines: from US$237 (direct)

Plan the rest of your trip to Chicago

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Questions about Toronto to Chicago flights

How much do flights from Toronto to Chicago cost? Fares we've seen start from US$139 on 14 Oct 2026 with Porter. Fares change quickly, so look before you book.

When can I save on flights from Toronto to Chicago? Among the next six months we checked, October 2026 had fares from US$139 in our data, while December 2026 reached US$237. Prices vary by date, so compare several days and save.

Which airlines fly from Toronto to Chicago? We've seen fares from Porter, United, Air Canada, American Airlines. This reflects recent searches, not a complete timetable.

Are there direct flights from Toronto to Chicago? Yes, we've seen direct fares (11 of 13 recent fares were direct). Availability depends on the date.

Is FindMyFlight free to use? Yes. We never add anything to the fare. If you book through a partner link we may earn a commission from the partner, at no extra cost to you.