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Recent American Airlines flights to Chicago found by users

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Cheap American Airlines Flight Deals to Chicago

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6:00 a.m. - 7:15 a.m.YYZ-ORD

2h 15mdirect

6:05 a.m. - 11:56 a.m.ORD-YYZ

4h 51m1 stop

C$ 266American Airlines

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Wed, 26 Nov - Sun, 7 Dec

6:00 a.m. - 7:15 a.m.YYZ-ORD

2h 15mdirect

5:00 a.m. - 11:02 a.m.ORD-YYZ

5h 02m1 stop

C$ 270American Airlines

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Fri, 5 Dec - Sun, 14 Dec

6:00 a.m. - 7:15 a.m.YYZ-ORD

2h 15mdirect

9:39 a.m. - 12:30 p.m.ORD-YYZ

1h 51mdirect

C$ 277American Airlines

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Tue, 9 Dec - Tue, 16 Dec

7:09 p.m. - 11:39 p.m.YYZ-ORD

5h 30m1 stop

6:05 a.m. - 11:56 a.m.ORD-YYZ

4h 51m1 stop

C$ 284American Airlines

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Fri, 5 Dec - Sun, 7 Dec

11:51 a.m. - 4:05 p.m.YYZ-ORD

5h 14m1 stop

5:00 a.m. - 11:02 a.m.ORD-YYZ

5h 02m1 stop

C$ 287American Airlines

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Wed, 26 Nov - Sun, 7 Dec

6:00 a.m. - 7:15 a.m.YYZ-ORD

2h 15mdirect

8:10 a.m. - 10:56 a.m.ORD-YYZ

1h 46mdirect

C$ 293American Airlines

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Wed, 10 Dec - Fri, 12 Dec

11:32 a.m. - 12:27 p.m.YYZ-ORD

1h 55mdirect

8:29 a.m. - 3:37 p.m.ORD-YYZ

6h 08m1 stop

C$ 298American Airlines

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Tue, 25 Nov - Wed, 17 Dec

6:00 a.m. - 7:15 a.m.YYZ-ORD

2h 15mdirect

5:00 a.m. - 11:02 a.m.ORD-YYZ

5h 02m1 stop

C$ 307American Airlines

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Fri, 5 Dec - Sun, 7 Dec

6:00 a.m. - 12:56 p.m.YYZ-ORD

7h 56m1 stop

5:00 a.m. - 11:02 a.m.ORD-YYZ

5h 02m1 stop

C$ 312American Airlines

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Thu, 27 Nov - Thu, 4 Dec

6:00 a.m. - 7:15 a.m.YYZ-ORD

2h 15mdirect

3:00 p.m. - 5:40 p.m.ORD-YYZ

1h 40mdirect

C$ 321American Airlines

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Tue, 25 Nov - Fri, 28 Nov

American Airlines flights to Chicago at a glance

Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	1 airport

The fastest flight from Canada to Chicago takes 1h 55m

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Direct flights go from Canada to Chicago every day.

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There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

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Insights on American Airlines flights to Chicago

Data designed to help you find the right flight

What is the cheapest month to fly Economy Class to Chicago?

In general, April is the cheapest month to fly Economy Class from Canada to Chicago. Due to it being the ‘off-season’ during this time, you can expect Economy Class flight prices to be around C$ 375. If you aren’t able to travel during the month of April, then book Economy Class flights to Chicago from Canada during January instead. Economy Class flights to Chicago in January, while not as cheap as those in April, still average around C$ 385.

What is the cheapest day to depart on your Economy Class flight to Chicago?

The cheapest day to depart from Canada to Chicago is on a Thursday when prices can be found for as low as C$ 263. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average Economy Class ticket price to Chicago on a Monday is C$ 375.

What cabin class options are available on Canada to Chicago flights?

There is only 1 cabin class available to choose from on Canada to Chicago flights.

Frequently asked questions about flights to Chicago with American Airlines

Is American Airlines generally cheaper than other airlines for flights to Chicago?

Lots of factors influence the price of a flight, whether that's with American Airlines or other airlines, so it is best to search and compare before booking. The airline flying to Chicago with the cheapest average round-trip price tends to be Porter Airlines.