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 $124 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 - $124, two-way – $213.
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Below is a detailed 2019 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 AA3736 American Airlines
Toronto — Chicago
1h 52m
Find flight
from$166
3:12 pm — 4:08 pm
3:12 pm — 4:08 pm AA3080 American Airlines
Toronto — Chicago
1h 56m
Find flight
from$131
7:57 pm — 8:54 pm
7:57 pm — 8:54 pm AA3033 American Airlines
Toronto — Chicago
1h 57m
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from$132
8:16 am — 9:11 am
8:16 am — 9:11 am AA2352 American Airlines
Toronto — Chicago
1h 55m
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from$132
11:04 am — 7:27 am
+1 day
11:04 am — 12:40 pm AA4864 American Airlines
Toronto — Philadelphia
17h 25m stop
6:05 am — 7:27 am AA2164 American Airlines
Philadelphia — Chicago
21h 23m
including layover
Find flight
from$168
12:15 pm — 6:18 am
+1 day
12:15 pm — 2:16 pm AA5698 American Airlines
Toronto — Charlotte
14h 59m stop
5:15 am — 6:18 am AA2938 American Airlines
Charlotte — Chicago
19h 3m
including layover
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from$188
12:15 pm — 5:18 pm
12:15 pm — 2:16 pm AA5698 American Airlines
Toronto — Charlotte
2h 4m stop
4:20 pm — 5:18 pm AA1017 American Airlines
Charlotte — Chicago
6h 3m
including layover
Find flight
from$240
12:15 pm — 6:58 pm
12:15 pm — 2:16 pm AA5698 American Airlines
Toronto — Charlotte
3h 44m stop
6:00 pm — 6:58 pm AA2488 American Airlines
Charlotte — Chicago
7h 43m
including layover
Find flight
from$282
3:19 pm — 7:26 pm
3:19 pm — 5:04 pm AA4901 American Airlines
Toronto — Philadelphia
44m stop
5:48 pm — 7:26 pm AA490 American Airlines
Philadelphia — Chicago
5h 7m
including layover
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from$240
3:40 pm — 11:08 pm
3:40 pm — 5:20 pm AA4664 American Airlines
Toronto — New York
4h 10m stop
9:30 pm — 11:08 pm AA2461 American Airlines
New York — Chicago
8h 28m
including layover
Find flight
from$154
3:40 pm — 10:17 pm
3:40 pm — 5:20 pm AA4664 American Airlines
Toronto — New York
3h 10m stop
8:30 pm — 10:17 pm AA196 American Airlines
New York — Chicago
7h 37m
including layover
Find flight
from$154
3:55 pm — 11:28 pm
3:55 pm — 6:09 pm AA2943 American Airlines
Toronto — Charlotte
4h 21m stop
10:30 pm — 11:28 pm AA483 American Airlines
Charlotte — Chicago
8h 33m
including layover
Find flight
from$124
3:55 pm — 8:33 am
+1 day
3:55 pm — 6:09 pm AA2943 American Airlines
Toronto — Charlotte
13h 26m stop
7:35 am — 8:33 am AA1668 American Airlines
Charlotte — Chicago
17h 38m
including layover
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from$124
3:55 pm — 8:57 pm
3:55 pm — 6:09 pm AA2943 American Airlines
Toronto — Charlotte
1h 50m stop
7:59 pm — 8:57 pm AA583 American Airlines
Charlotte — Chicago
6h 2m
including layover
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from$124
5:55 pm — 10:50 pm
5:55 pm — 7:41 pm AA4931 American Airlines
Toronto — Philadelphia
1h 44m stop
9:25 pm — 10:50 pm AA1680 American Airlines
Philadelphia — Chicago
5h 55m
including layover
Find flight
from$124
6:00 am — 10:33 am
6:00 am — 8:12 am AA5665 American Airlines
Toronto — Charlotte
1h 23m stop
9:35 am — 10:33 am AA2080 American Airlines
Charlotte — Chicago
5h 33m
including layover
Find flight
from$166
6:10 pm — 6:22 am
+1 day
6:10 pm — 7:50 pm AA4931 American Airlines
Toronto — Philadelphia
9h 10m stop
5:00 am — 6:22 am AA2324 American Airlines
Philadelphia — Chicago
13h 12m
including layover
Find flight
from$124
6:10 pm — 7:27 am
+1 day
6:10 pm — 7:50 pm AA4931 American Airlines
Toronto — Philadelphia
10h 15m stop
6:05 am — 7:27 am AA2164 American Airlines
Philadelphia — Chicago
14h 17m
including layover
Find flight
from$124
6:15 am — 10:31 am
6:15 am — 8:03 am AA5603 American Airlines
Toronto — Washington D.C.
1h 32m stop
9:35 am — 10:31 am AA1167 American Airlines
Washington D.C. — Chicago
5h 16m
including layover
Find flight
from$166
6:30 am — 10:53 am
6:30 am — 8:12 am AA3955 American Airlines
Toronto — New York
1h 18m stop
9:30 am — 10:53 am AA129 American Airlines
New York — Chicago
5h 23m
including layover
Find flight
from$166
7:15 am — 12:28 pm
7:15 am — 9:18 am AA5689 American Airlines
Toronto — Charlotte
2h 12m stop
11:30 am — 12:28 pm AA2817 American Airlines
Charlotte — Chicago
6h 13m
including layover
Find flight
from$166
7:15 pm — 11:28 pm
7:15 pm — 9:22 pm AA5705 American Airlines
Toronto — Charlotte
1h 8m stop
10:30 pm — 11:28 pm AA483 American Airlines
Charlotte — Chicago
5h 13m
including layover
Find flight
from$124
7:15 pm — 8:33 am
+1 day
7:15 pm — 9:22 pm AA5705 American Airlines
Toronto — Charlotte
10h 13m stop
7:35 am — 8:33 am AA1668 American Airlines
Charlotte — Chicago
14h 18m
including layover
Find flight
from$124
7:15 pm — 6:18 am
+1 day
7:15 pm — 9:22 pm AA5705 American Airlines
Toronto — Charlotte
7h 53m stop
5:15 am — 6:18 am AA2938 American Airlines
Charlotte — Chicago
12h 3m
including layover
Find flight
from$124
8:27 am — 12:38 pm
8:27 am — 10:10 am AA4887 American Airlines
Toronto — Philadelphia
55m stop
11:05 am — 12:38 pm AA1920 American Airlines
Philadelphia — Chicago
5h 11m
including layover
Find flight
from$124
8:27 am — 11:13 pm
8:27 am — 10:10 am AA4887 American Airlines
Toronto — Philadelphia
11h 30m stop
9:40 pm — 11:13 pm AA1680 American Airlines
Philadelphia — Chicago
15h 46m
including layover
Find flight
from$124
9:10 am — 9:51 pm
9:10 am — 11:00 am AA5603 American Airlines
Toronto — Washington D.C.
9h 55m stop
8:55 pm — 9:51 pm AA2679 American Airlines
Washington D.C. — Chicago
13h 41m
including layover
Find flight
from$139
9:10 am — 6:26 pm
9:10 am — 11:00 am AA5603 American Airlines
Toronto — Washington D.C.
6h 30m stop
5:30 pm — 6:26 pm AA1486 American Airlines
Washington D.C. — Chicago
10h 16m
including layover
Find flight
from$166
9:10 am — 8:11 pm
9:10 am — 11:00 am AA5603 American Airlines
Toronto — Washington D.C.
8h 15m stop
7:15 pm — 8:11 pm AA4100 American Airlines
Washington D.C. — Chicago
12h 1m
including layover
Find flight
from$251
9:15 am — 7:26 pm
9:15 am — 10:53 am AA4887 American Airlines
Toronto — Philadelphia
6h 55m stop
5:48 pm — 7:26 pm AA490 American Airlines
Philadelphia — Chicago
11h 11m
including layover
Find flight
from$188
*Departure and arrival times are local. Last updated on 10/17/2019

Flight Information

There are 4 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 11:04 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 11:04 am
  • The latest flight 9:15 am
  • Distance 436 ml

The cheapest months for traveling to Chicago are october, december, september, The most expensive and popular months are june, november, february.

The cheapest flight by American Airlines that our users were able to find is $124. This airfare is economy class on one-way AA4887 flight for October 15, 2019 leaving Pearson International in Toronto at 8:27 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides American Airlines there are other 5 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 18 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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