American Airlines Toronto to Chicago Flights

Cheapflightsplus.com will find cheap American Airlines flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $103 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of American Airlines, arrivals and departure details below.

Find Cheap Airfare Toronto (ON) — Chicago (IL) by American Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in october: one-way - $103, two-way – $177.
Direct flights
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Below is a detailed 2020 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
11:45 am — 12:37 pm
11:45 am — 12:37 pm AA3236 American Airlines
Toronto — Chicago
1h 52m
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from$150
3:12 pm — 4:08 pm
3:12 pm — 4:08 pm AA3080 American Airlines
Toronto — Chicago
1h 56m
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from$151
6:30 pm — 7:31 pm
6:30 pm — 7:31 pm AA3526 American Airlines
Toronto — Chicago
2h 1m
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from$115
7:57 pm — 8:54 pm
7:57 pm — 8:54 pm AA3033 American Airlines
Toronto — Chicago
1h 57m
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from$115
8:16 am — 9:11 am
8:16 am — 9:11 am AA2352 American Airlines
Toronto — Chicago
1h 55m
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from$115
10:59 am — 7:39 am
+1 day
10:59 am — 12:45 pm AA5517 American Airlines
Toronto — Washington D.C.
17h 45m stop
6:30 am — 7:39 am AA466 American Airlines
Washington D.C. — Chicago
21h 40m
including layover
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from$108
11:00 am — 8:46 pm
11:00 am — 12:46 pm AA5517 American Airlines
Toronto — Washington D.C.
6h 43m stop
7:29 pm — 8:46 pm AA1015 American Airlines
Washington D.C. — Chicago
10h 46m
including layover
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from$108
12:14 pm — 6:20 am
+1 day
12:14 pm — 2:19 pm AA5137 American Airlines
Toronto — Charlotte
14h 56m stop
5:15 am — 6:20 am AA226 American Airlines
Charlotte — Chicago
19h 6m
including layover
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from$140
1:27 pm — 10:04 pm
1:27 pm — 3:08 pm AA3386 American Airlines
Toronto — New York
5h 22m stop
8:30 pm — 10:04 pm AA196 American Airlines
New York — Chicago
9h 37m
including layover
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from$108
2:33 pm — 10:06 pm
2:33 pm — 4:15 pm AA3350 American Airlines
Toronto — New York
4h 15m stop
8:30 pm — 10:06 pm AA30 American Airlines
New York — Chicago
8h 33m
including layover
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from$103
3:02 pm — 11:23 pm
3:02 pm — 4:43 pm AA3350 American Airlines
Toronto — New York
5h 17m stop
10:00 pm — 11:23 pm AA222 American Airlines
New York — Chicago
9h 21m
including layover
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from$103
5:22 pm — 10:12 pm
5:22 pm — 7:20 pm AA5542 American Airlines
Toronto — Washington D.C.
1h 43m stop
9:03 pm — 10:12 pm AA2679 American Airlines
Washington D.C. — Chicago
5h 50m
including layover
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from$108
6:30 am — 11:23 pm
6:30 am — 8:17 am AA3955 American Airlines
Toronto — New York
13h 43m stop
10:00 pm — 11:23 pm AA222 American Airlines
New York — Chicago
17h 53m
including layover
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from$103
7:00 am — 12:29 pm
7:00 am — 8:38 am AA4992 American Airlines
Toronto — Philadelphia
2h 18m stop
10:56 am — 12:29 pm AA1920 American Airlines
Philadelphia — Chicago
6h 29m
including layover
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from$103
8:27 am — 5:17 pm
8:27 am — 10:10 am AA4887 American Airlines
Toronto — Philadelphia
5h 30m stop
3:40 pm — 5:17 pm AA1941 American Airlines
Philadelphia — Chicago
9h 50m
including layover
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from$108
9:15 am — 6:10 pm
9:15 am — 10:50 am AA4887 American Airlines
Toronto — Philadelphia
5h 57m stop
4:47 pm — 6:10 pm AA2374 American Airlines
Philadelphia — Chicago
9h 55m
including layover
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from$108
*Departure and arrival times are local. Last updated on 09/23/2020

Flight Information

There are 7 flights by American Airlines from Toronto to Chicago every week with departures from Pearson International, Toronto Island, Buttonville Municipal. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:25 am to 9:15 am. Nonstop flight is 1h 52m. The time difference between Toronto and Chicago is 1h.

  • The fastest flight 1h 52m
  • Average flight time 1h 56m
  • The earliest flight 10:25 am
  • The latest flight 9:15 am
  • Distance 436 ml

The cheapest months for traveling to Chicago are october (from 108 $).

The cheapest flight by American Airlines that our users were able to find is $103. This airfare is economy class on one-way AA3955 flight for August 27, 2019 leaving Pearson International in Toronto at 6:30 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides American Airlines there are other 2 airline carriers between Toronto and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Toronto to Chicago.

Nonstop flights

There are 8 direct flights every day from Toronto. Airlines and fares are below:

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Connecting Flights

List of flights with layovers (1 and more stops):

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How to book an air ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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