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 $134 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 march: one-way - $134, two-way – $230.
Direct flights
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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
11:48 am — 12:45 pm
11:48 am — 12:45 pm AA3439 American Airlines
Toronto — Chicago
1h 57m
Find flight
from$244
3:11 pm — 4:09 pm
3:11 pm — 4:09 pm AA3080 American Airlines
Toronto — Chicago
1h 58m
Find flight
from$201
6:22 pm — 7:25 pm
6:22 pm — 7:25 pm AA3284 American Airlines
Toronto — Chicago
2h 3m
Find flight
from$244
7:56 pm — 8:53 pm
7:56 pm — 8:53 pm AA3033 American Airlines
Toronto — Chicago
1h 57m
Find flight
from$201
8:15 am — 9:21 am
8:15 am — 9:21 am AA3430 American Airlines
Toronto — Chicago
2h 6m
Find flight
from$264
10:21 am — 3:13 pm
10:21 am — 12:00 pm AA4555 American Airlines
Toronto — New York
1h 30m stop
1:30 pm — 3:13 pm AA30 American Airlines
New York — Chicago
5h 52m
including layover
Find flight
from$205
10:21 am — 4:08 pm
10:21 am — 12:00 pm AA4555 American Airlines
Toronto — New York
2h 30m stop
2:30 pm — 4:08 pm AA114 American Airlines
New York — Chicago
6h 47m
including layover
Find flight
from$250
10:21 am — 6:20 pm
10:21 am — 12:00 pm AA4555 American Airlines
Toronto — New York
4h 30m stop
4:30 pm — 6:20 pm AA194 American Airlines
New York — Chicago
8h 59m
including layover
Find flight
from$278
10:47 am — 7:28 am
+1 day
10:47 am — 12:25 pm AA4864 American Airlines
Toronto — Philadelphia
17h 40m stop
6:05 am — 7:28 am AA892 American Airlines
Philadelphia — Chicago
21h 41m
including layover
Find flight
from$206
10:47 am — 6:10 am
+1 day
10:47 am — 12:25 pm AA4864 American Airlines
Toronto — Philadelphia
16h 35m stop
5:00 am — 6:10 am AA2324 American Airlines
Philadelphia — Chicago
20h 23m
including layover
Find flight
from$206
10:47 am — 5:16 pm
10:47 am — 12:25 pm AA4864 American Airlines
Toronto — Philadelphia
3h 15m stop
3:40 pm — 5:16 pm AA828 American Airlines
Philadelphia — Chicago
7h 29m
including layover
Find flight
from$406
10:47 am — 5:21 pm
10:47 am — 12:25 pm AA4864 American Airlines
Toronto — Philadelphia
3h 18m stop
3:43 pm — 5:21 pm AA2181 American Airlines
Philadelphia — Chicago
7h 34m
including layover
Find flight
from$588
10:58 am — 10:12 pm
10:58 am — 12:53 pm AA4261 American Airlines
Toronto — Washington D.C.
8h 7m stop
9:00 pm — 10:12 pm AA2499 American Airlines
Washington D.C. — Chicago
12h 14m
including layover
Find flight
from$206
10:59 am — 3:46 pm
10:59 am — 12:54 pm AA4261 American Airlines
Toronto — Washington D.C.
1h 36m stop
2:30 pm — 3:46 pm AA1609 American Airlines
Washington D.C. — Chicago
5h 47m
including layover
Find flight
from$206
10:59 am — 6:57 pm
10:59 am — 12:54 pm AA4261 American Airlines
Toronto — Washington D.C.
4h 36m stop
5:30 pm — 6:57 pm AA1486 American Airlines
Washington D.C. — Chicago
8h 58m
including layover
Find flight
from$278
12:14 pm — 7:03 pm
12:14 pm — 1:56 pm AA3957 American Airlines
Toronto — New York
3h 9m stop
5:05 pm — 7:03 pm AA1414 American Airlines
New York — Chicago
7h 49m
including layover
Find flight
from$278
12:15 pm — 7:25 pm
12:15 pm — 2:42 pm AA3470 American Airlines
Toronto — Dallas
2h 13m stop
4:55 pm — 7:25 pm AA1463 American Airlines
Dallas — Chicago
8h 10m
including layover
Find flight
from$510
12:15 pm — 6:47 pm
12:15 pm — 2:42 pm AA3470 American Airlines
Toronto — Dallas
1h 38m stop
4:20 pm — 6:47 pm AA2418 American Airlines
Dallas — Chicago
7h 32m
including layover
Find flight
from$603
12:30 pm — 11:54 pm
12:30 pm — 2:43 pm AA5612 American Airlines
Toronto — Charlotte
8h 12m stop
10:55 pm — 11:54 pm AA483 American Airlines
Charlotte — Chicago
12h 24m
including layover
Find flight
from$206
12:30 pm — 11:00 pm
12:30 pm — 2:08 pm AA3386 American Airlines
Toronto — New York
7h 22m stop
9:30 pm — 11:00 pm AA2461 American Airlines
New York — Chicago
11h 30m
including layover
Find flight
from$235
12:30 pm — 10:06 pm
12:30 pm — 2:08 pm AA3386 American Airlines
Toronto — New York
6h 21m stop
8:29 pm — 10:06 pm AA196 American Airlines
New York — Chicago
10h 36m
including layover
Find flight
from$250
12:30 pm — 6:20 pm
12:30 pm — 2:08 pm AA3386 American Airlines
Toronto — New York
2h 22m stop
4:30 pm — 6:20 pm AA194 American Airlines
New York — Chicago
6h 50m
including layover
Find flight
from$250
12:30 pm — 7:22 pm
12:30 pm — 2:08 pm AA3386 American Airlines
Toronto — New York
3h 22m stop
5:30 pm — 7:22 pm AA357 American Airlines
New York — Chicago
7h 52m
including layover
Find flight
from$250
12:35 pm — 5:54 pm
12:35 pm — 2:43 pm AA5612 American Airlines
Toronto — Charlotte
1h 48m stop
4:31 pm — 5:54 pm AA1017 American Airlines
Charlotte — Chicago
6h 19m
including layover
Find flight
from$206
12:35 pm — 7:16 pm
12:35 pm — 2:43 pm AA5612 American Airlines
Toronto — Charlotte
3h 16m stop
5:59 pm — 7:16 pm AA2488 American Airlines
Charlotte — Chicago
7h 41m
including layover
Find flight
from$278
2:50 pm — 10:06 pm
2:50 pm — 4:28 pm AA4664 American Airlines
Toronto — New York
4h 1m stop
8:29 pm — 10:06 pm AA196 American Airlines
New York — Chicago
8h 16m
including layover
Find flight
from$227
2:50 pm — 11:00 pm
2:50 pm — 4:28 pm AA4664 American Airlines
Toronto — New York
5h 2m stop
9:30 pm — 11:00 pm AA2461 American Airlines
New York — Chicago
9h 10m
including layover
Find flight
from$235
2:50 pm — 7:22 pm
2:50 pm — 4:28 pm AA4664 American Airlines
Toronto — New York
1h 2m stop
5:30 pm — 7:22 pm AA357 American Airlines
New York — Chicago
5h 32m
including layover
Find flight
from$250
2:50 pm — 8:09 am
+1 day
2:50 pm — 4:28 pm AA4664 American Airlines
Toronto — New York
14h 2m stop
6:30 am — 8:09 am AA349 American Airlines
New York — Chicago
18h 19m
including layover
Find flight
from$250
2:50 pm — 9:17 pm
2:50 pm — 4:28 pm AA4664 American Airlines
Toronto — New York
3h 2m stop
7:30 pm — 9:17 pm AA336 American Airlines
New York — Chicago
7h 27m
including layover
Find flight
from$278
2:50 pm — 8:22 pm
2:50 pm — 4:28 pm AA4664 American Airlines
Toronto — New York
2h 2m stop
6:30 pm — 8:22 pm AA380 American Airlines
New York — Chicago
6h 32m
including layover
Find flight
from$278
2:50 pm — 9:14 am
+1 day
2:50 pm — 4:28 pm AA4664 American Airlines
Toronto — New York
15h 2m stop
7:30 am — 9:14 am AA370 American Airlines
New York — Chicago
19h 24m
including layover
Find flight
from$356
3:21 pm — 7:28 am
+1 day
3:21 pm — 5:05 pm AA4901 American Airlines
Toronto — Philadelphia
13h stop
6:05 am — 7:28 am AA892 American Airlines
Philadelphia — Chicago
17h 7m
including layover
Find flight
from$250
3:21 pm — 10:54 pm
3:21 pm — 5:05 pm AA4901 American Airlines
Toronto — Philadelphia
4h 20m stop
9:25 pm — 10:54 pm AA1680 American Airlines
Philadelphia — Chicago
8h 33m
including layover
Find flight
from$336
3:21 pm — 9:11 am
+1 day
3:21 pm — 5:05 pm AA4901 American Airlines
Toronto — Philadelphia
14h 40m stop
7:45 am — 9:11 am AA2098 American Airlines
Philadelphia — Chicago
18h 50m
including layover
Find flight
from$356
3:21 pm — 7:32 pm
3:21 pm — 5:05 pm AA4901 American Airlines
Toronto — Philadelphia
45m stop
5:50 pm — 7:32 pm AA490 American Airlines
Philadelphia — Chicago
5h 11m
including layover
Find flight
from$622
3:53 pm — 11:56 pm
3:53 pm — 6:13 pm AA5079 American Airlines
Toronto — Charlotte
4h 42m stop
10:55 pm — 11:56 pm AA483 American Airlines
Charlotte — Chicago
9h 3m
including layover
Find flight
from$206
3:53 pm — 9:16 pm
3:53 pm — 6:13 pm AA5079 American Airlines
Toronto — Charlotte
1h 48m stop
8:01 pm — 9:16 pm AA2760 American Airlines
Charlotte — Chicago
6h 23m
including layover
Find flight
from$278
3:53 pm — 8:50 am
+1 day
3:53 pm — 6:13 pm AA5079 American Airlines
Toronto — Charlotte
13h 23m stop
7:36 am — 8:50 am AA462 American Airlines
Charlotte — Chicago
17h 57m
including layover
Find flight
from$278
5:20 pm — 10:12 pm
5:20 pm — 7:10 pm AA4238 American Airlines
Toronto — Washington D.C.
1h 50m stop
9:00 pm — 10:12 pm AA2499 American Airlines
Washington D.C. — Chicago
5h 52m
including layover
Find flight
from$206
5:56 pm — 10:54 pm
5:56 pm — 7:39 pm AA4931 American Airlines
Toronto — Philadelphia
1h 46m stop
9:25 pm — 10:54 pm AA1680 American Airlines
Philadelphia — Chicago
5h 58m
including layover
Find flight
from$406
5:58 pm — 1:01 am
+1 day
5:58 pm — 8:28 pm AA1111 American Airlines
Toronto — Dallas
2h 7m stop
10:35 pm — 1:01 am AA2585 American Airlines
Dallas — Chicago
8h 3m
including layover
Find flight
from$498
6:11 pm — 6:21 am
+1 day
6:11 pm — 7:56 pm AA4931 American Airlines
Toronto — Philadelphia
9h 4m stop
5:00 am — 6:21 am AA2324 American Airlines
Philadelphia — Chicago
13h 10m
including layover
Find flight
from$134
6:15 am — 10:47 am
6:15 am — 8:09 am AA4299 American Airlines
Toronto — Washington D.C.
1h 26m stop
9:35 am — 10:47 am AA1167 American Airlines
Washington D.C. — Chicago
5h 32m
including layover
Find flight
from$152
6:15 am — 12:14 pm
6:15 am — 8:09 am AA4299 American Airlines
Toronto — Washington D.C.
2h 54m stop
11:03 am — 12:14 pm AA1033 American Airlines
Washington D.C. — Chicago
6h 59m
including layover
Find flight
from$153
6:15 am — 1:58 pm
6:15 am — 8:09 am AA4299 American Airlines
Toronto — Washington D.C.
4h 31m stop
12:40 pm — 1:58 pm AA985 American Airlines
Washington D.C. — Chicago
8h 43m
including layover
Find flight
from$153
6:15 am — 3:46 pm
6:15 am — 8:09 am AA4299 American Airlines
Toronto — Washington D.C.
6h 21m stop
2:30 pm — 3:46 pm AA1609 American Airlines
Washington D.C. — Chicago
10h 31m
including layover
Find flight
from$153
6:30 am — 2:07 pm
6:30 am — 8:19 am AA3955 American Airlines
Toronto — New York
4h 10m stop
12:29 pm — 2:07 pm AA367 American Airlines
New York — Chicago
8h 37m
including layover
Find flight
from$206
6:30 am — 11:16 am
6:30 am — 8:19 am AA3955 American Airlines
Toronto — New York
1h 11m stop
9:30 am — 11:16 am AA129 American Airlines
New York — Chicago
5h 46m
including layover
Find flight
from$206
6:30 am — 3:13 pm
6:30 am — 8:15 am AA3955 American Airlines
Toronto — New York
5h 15m stop
1:30 pm — 3:13 pm AA30 American Airlines
New York — Chicago
9h 43m
including layover
Find flight
from$206
6:30 am — 12:18 pm
6:30 am — 8:15 am AA3955 American Airlines
Toronto — New York
2h 15m stop
10:30 am — 12:18 pm AA2302 American Airlines
New York — Chicago
6h 48m
including layover
Find flight
from$206
6:30 am — 1:10 pm
6:30 am — 8:19 am AA3955 American Airlines
Toronto — New York
3h 11m stop
11:30 am — 1:10 pm AA337 American Airlines
New York — Chicago
7h 40m
including layover
Find flight
from$206
7:00 am — 12:44 pm
7:00 am — 9:26 am AA1169 American Airlines
Toronto — Dallas
53m stop
10:19 am — 12:44 pm AA1258 American Airlines
Dallas — Chicago
6h 44m
including layover
Find flight
from$498
7:00 am — 1:35 pm
7:00 am — 9:32 am AA1169 American Airlines
Toronto — Dallas
1h 33m stop
11:05 am — 1:35 pm AA319 American Airlines
Dallas — Chicago
7h 35m
including layover
Find flight
from$498
7:15 pm — 11:56 pm
7:15 pm — 9:32 pm AA5631 American Airlines
Toronto — Charlotte
1h 23m stop
10:55 pm — 11:56 pm AA483 American Airlines
Charlotte — Chicago
5h 41m
including layover
Find flight
from$206
7:17 am — 2:09 pm
7:17 am — 8:52 am AA4992 American Airlines
Toronto — Philadelphia
3h 54m stop
12:46 pm — 2:09 pm AA2011 American Airlines
Philadelphia — Chicago
7h 52m
including layover
Find flight
from$278
7:17 am — 12:34 pm
7:17 am — 8:52 am AA4992 American Airlines
Toronto — Philadelphia
2h 9m stop
11:01 am — 12:34 pm AA2095 American Airlines
Philadelphia — Chicago
6h 17m
including layover
Find flight
from$298
7:20 am — 12:31 pm
7:20 am — 8:52 am AA4992 American Airlines
Toronto — Philadelphia
2h 8m stop
11:00 am — 12:31 pm AA806 American Airlines
Philadelphia — Chicago
6h 11m
including layover
Find flight
from$278
7:30 am — 12:37 pm
7:30 am — 9:47 am AA5660 American Airlines
Toronto — Charlotte
1h 38m stop
11:25 am — 12:37 pm AA864 American Airlines
Charlotte — Chicago
6h 7m
including layover
Find flight
from$152
7:30 am — 2:14 pm
7:30 am — 9:45 am AA5660 American Airlines
Toronto — Charlotte
3h 22m stop
1:07 pm — 2:14 pm AA1650 American Airlines
Charlotte — Chicago
7h 44m
including layover
Find flight
from$153
7:30 am — 3:44 pm
7:30 am — 9:47 am AA5660 American Airlines
Toronto — Charlotte
4h 47m stop
2:34 pm — 3:44 pm AA1883 American Airlines
Charlotte — Chicago
9h 14m
including layover
Find flight
from$153
7:30 am — 5:47 pm
7:30 am — 9:45 am AA5660 American Airlines
Toronto — Charlotte
6h 45m stop
4:30 pm — 5:47 pm AA1017 American Airlines
Charlotte — Chicago
11h 17m
including layover
Find flight
from$153
7:30 am — 11:56 pm
7:30 am — 9:47 am AA5660 American Airlines
Toronto — Charlotte
13h 8m stop
10:55 pm — 11:56 pm AA483 American Airlines
Charlotte — Chicago
17h 26m
including layover
Find flight
from$156
9:18 am — 2:09 pm
9:18 am — 10:54 am AA4887 American Airlines
Toronto — Philadelphia
1h 52m stop
12:46 pm — 2:09 pm AA2011 American Airlines
Philadelphia — Chicago
5h 51m
including layover
Find flight
from$250
9:18 am — 5:16 pm
9:18 am — 10:54 am AA4887 American Airlines
Toronto — Philadelphia
4h 46m stop
3:40 pm — 5:16 pm AA828 American Airlines
Philadelphia — Chicago
8h 58m
including layover
Find flight
from$336
9:18 am — 7:32 pm
9:18 am — 10:54 am AA4887 American Airlines
Toronto — Philadelphia
6h 56m stop
5:50 pm — 7:32 pm AA490 American Airlines
Philadelphia — Chicago
11h 14m
including layover
Find flight
from$500
9:18 am — 5:21 pm
9:18 am — 10:54 am AA4887 American Airlines
Toronto — Philadelphia
4h 49m stop
3:43 pm — 5:21 pm AA2181 American Airlines
Philadelphia — Chicago
9h 3m
including layover
Find flight
from$521
2:50 pm — 9:16 pm
2:50 pm — 4:28 pm AA4664 American Airlines
Toronto — New York
46m stop
5:14 pm — 7:24 pm AA2068 American Airlines
New York — Charlotte
37m stop
8:01 pm — 9:16 pm AA2760 American Airlines
Charlotte — Chicago
7h 26m
including layover
Find flight
from$527
6:30 am — 1:18 pm
6:30 am — 8:15 am AA3955 American Airlines
Toronto — New York
45m stop
9:00 am — 10:58 am AA4528 American Airlines
New York — Columbus
1h 54m stop
12:52 pm — 1:18 pm AA3854 American Airlines
Columbus — Chicago
7h 48m
including layover
Find flight
from$292
*Departure and arrival times are local. Last updated on 02/19/2019

Flight Information

There are 5 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 10:21 am to 9:18 am. Nonstop flight is 1h 57m. The time difference between Toronto and Chicago is 1h.

  • The fastest flight 1h 57m
  • Average flight time 1h 58m
  • The earliest flight 10:21 am
  • The latest flight 9:18 am
  • Distance 436 ml

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

The cheapest flight by American Airlines that our users were able to find is $134. This airfare is economy class on one-way AA4931 flight for February 23, 2019 leaving Pearson International in Toronto at 6:11 pm, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides American Airlines there are other 3 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 12 direct flights every day from Toronto. Airlines and fares are below:

See more direct flights

Connecting Flights

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

See more connecting flights

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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