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Find cheap American Airlines flights to Chicago

CMH — CHI
26 Aug — 2 Sep1
1 adult
1 adult, Economy, 0 bags

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Cheapest American Airlines flights from Canada to Chicago
Explore the most affordable American Airlines flight options available from Canada to Chicago. Find the lowest fares with prices last updated on 27 July 2026.

Thu 27/82:15 p.m.
YYZ
-
ORD
1 stop5h 39m
American Airlines
Sat 12/93:00 p.m.
ORD
-
YYZ
1 stop5h 43m
American Airlines
Deal found 26/7C$ 361
Fri 28/87:15 p.m.
YYZ
-
ORD
Nonstop2h 05m
American Airlines
Mon 31/87:03 a.m.
ORD
-
YYZ
1 stop5h 23m
American Airlines
Deal found 27/7C$ 368
Tue 18/87:20 a.m.
YYZ
-
ORD
Nonstop2h 10m
American Airlines
Thu 17/98:30 p.m.
ORD
-
YYZ
Nonstop1h 56m
American Airlines
Deal found 27/7C$ 369

Flights to Chicago with American Airlines at a glance

Find detailed information about American Airlines flights from Canada to Chicago. Explore the options provided by American Airlines to plan your journey from Canada to Chicago. Data last updated 27 July 2026.

Popular in

July

Cheapest in

January

Average price

C$ 431

Round-trip from

C$ 321

One-way from

C$ 192

Good round-trip deal

C$ 667 or less

Good one-way deal

C$ 326 or less
Highest demand for flights to Chicago with American Airlines; 12% potential price increase.
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Best time to find cheap flights to Chicago with American Airlines; 2% potential price drop.
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Average price for flights to Chicago with American Airlines (round-trip).
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American Airlines
  • American Airlines
  • 10/9-12/9
  • 1 total stop
  • 9h 33m total
  • Canada to Chicago
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American Airlines
  • American Airlines
  • 6/9
  • Nonstop
  • 2h 05m total
  • Canada to Chicago
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Price to beat on a round-trip flight from Canada to Chicago with American Airlines.
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Price to beat on a one-way flight from Canada to Chicago with American Airlines.
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Cheapflights Insights

Find cheap American Airlines flights to Chicago

How long is the flight to Chicago with American Airlines?

On average, American Airlines flights from Canada to Chicago take 2 hours 28 minutes. Flights to Chicago from other popular cities in Canada will vary in length. Below are a few examples of popular routes and their flight times.

American Airlines weekly flight availability to Chicago

The most flights to Chicago operated by American Airlines are scheduled on a Saturday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (12 on average).

When is the cheapest time to fly to Chicago with American Airlines?

Users looking for the cheapest American Airlines fares to Chicago should consider flying on Friday mornings, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday afternoons, when prices are usually at their highest.

FAQs about flights to Chicago with American Airlines

  • Which airport do American Airlines flights arrive at when travelling to Chicago?

    American Airlines flights on this route tend to land at Chicago O'Hare Intl Airport.

  • Is American Airlines the cheapest airline for a flight to Chicago?

    Flight prices will depend on factors like date, time, and cabin class, so it is worth comparing flights before booking. Based on Cheapflights data, the cheapest average round-trip price for flights to Chicago tends to be with Porter Airlines.

  • Are there alternative airlines other than American Airlines that fly to Chicago?

    Air Canada, United Airlines and Porter Airlines all fly to Chicago and offer an alternative to American Airlines.

  • How much is a flight to Chicago with American Airlines?

    The average price for a round-trip with American Airlines is C$ 482, while a one-way flight costs around C$ 382.

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Reviews of American Airlines

See what Cheapflights users have to say about their American Airlines experience.
American Airlines
7.1
Good
10,000 reviews
Check prices
Overview

Crew

7.9

Comfort

7.2

Boarding

7.5

Entertainment

6.8

Food

6.4

Popular American Airlines flights

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Airports serving Chicago

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