American Airlines Toronto to Chicago Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap American Airlines flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $169 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 december: one-way - $169, two-way – $290.

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Cheap Flights from Toronto to Chicago by American Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by American Airlines, their prices start from $169. The fastest nonstop flight takes 2h. The fastest connecting flight — 4h 55m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $169 Find flight	11:37 am Toronto Pearson International	12:37 pm Chicago O'Hare International	2h 0m	American Airlines	AA3604
from $169 Find flight	6:15 am Toronto Pearson International	7:30 am Chicago O'Hare International	2h 15m	American Airlines	AA3524
from $230 Find flight	1:14 pm Toronto Pearson International	2:14 pm Chicago O'Hare International	2h 0m	American Airlines	AA3606
from $179 Find flight	3:50 pm Toronto Pearson International	8:33 pm Chicago O'Hare International	5h 43m layover 1h 25m - New York	American Airlines	AA4556 AA1263
from $179 Find flight	4:30 pm Toronto Pearson International	9:39 pm Chicago O'Hare International	6h 9m layover 1h 51m - Charlotte	American Airlines	AA5345 AA815
from $179 Find flight	5:15 pm Toronto Pearson International	10:05 pm Chicago O'Hare International	5h 50m layover 1h 46m - Washington D.C.	American Airlines	AA5667 AA1630
from $180 Find flight	12:39 pm Toronto Pearson International	7:45 pm Chicago O'Hare International	8h 6m layover 3h 59m - Philadelphia	American Airlines	AA5411 AA490
from $180 Find flight	10:57 am Toronto Pearson International	4:09 pm Chicago O'Hare International	6h 12m layover 2h 7m - Washington D.C.	American Airlines	AA5425 AA1682
from $180 Find flight	11:45 am Toronto Pearson International	7:11 pm Chicago O'Hare International	8h 26m layover 4h 1m - Charlotte	American Airlines	AA1720 AA2488
from $180 Find flight	6:00 am Toronto Pearson International	12:24 pm Chicago O'Hare International	7h 24m layover 2h 48m - Charlotte	American Airlines	AA5046 AA2279
from $180 Find flight	6:00 am Toronto Pearson International	3:40 pm Chicago O'Hare International	10h 40m layover 6h 7m - Charlotte	American Airlines	AA5046 AA614
from $180 Find flight	6:00 am Toronto Pearson International	2:10 pm Chicago O'Hare International	9h 10m layover 4h 35m - Charlotte	American Airlines	AA5046 AA1052
from $213 Find flight	1:54 pm Toronto Pearson International	10:06 pm Chicago O'Hare International	9h 12m layover 5h 0m - New York	American Airlines	AA4382 NK3386
from $285 Find flight	10:55 am Toronto Pearson International	8:33 pm Chicago O'Hare International	10h 38m layover 6h 15m - New York	American Airlines	AA4347 AA1263
from $176 Find flight	7:00 am Toronto Pearson International	2:10 pm Chicago O'Hare International	8h 10m layover 1h 9m - New York 0h 52m - Charlotte	American Airlines	AA4542 AA2036 AA1052
from $230 Find flight	10:30 am Toronto Pearson International	9:39 pm Chicago O'Hare International	12h 9m layover 2h 36m - New York 3h 32m - Charlotte	American Airlines	AA4552 AA327 AA815

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 12/21/2024

American Airlines Flight Schedule Toronto to Chicago

Below is a detailed 2025 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	Flight Details	Flight Time	Price
11:37 am — 12:37 pm	11:37 am — 12:37 pm AA3604 American Airlines Toronto — Chicago	2h	Find flight from$169
1:14 pm — 2:14 pm	1:14 pm — 2:14 pm AA3606 American Airlines Toronto — Chicago	2h	Find flight from$230
4:44 pm — 5:44 pm	4:44 pm — 5:44 pm AA3608 American Airlines Toronto — Chicago	2h	Find flight from$190
6:15 am — 7:30 am	6:15 am — 7:30 am AA3524 American Airlines Toronto — Chicago	2h 15m	Find flight from$169
10:55 am — 5:51 pm	10:55 am — 12:35 pm AA4347 American Airlines Toronto — New York 3h 32m stop 4:07 pm — 5:51 pm AA1240 American Airlines New York — Chicago	7h 56m including layover	Find flight from$200
10:57 am — 4:09 pm	10:57 am — 12:42 pm AA5425 American Airlines Toronto — Washington D.C. 2h 7m stop 2:49 pm — 4:09 pm AA1682 American Airlines Washington D.C. — Chicago	6h 12m including layover	Find flight from$180
11:45 am — 7:11 pm	11:45 am — 2:00 pm AA1720 American Airlines Toronto — Charlotte 4h 1m stop 6:01 pm — 7:11 pm AA2488 American Airlines Charlotte — Chicago	8h 26m including layover	Find flight from$180
12:39 pm — 7:45 pm	12:39 pm — 2:14 pm AA5411 American Airlines Toronto — Philadelphia 3h 59m stop 6:13 pm — 7:45 pm AA490 American Airlines Philadelphia — Chicago	8h 6m including layover	Find flight from$180
12:39 pm — 5:31 pm	12:39 pm — 2:14 pm AA5411 American Airlines Toronto — Philadelphia 1h 46m stop 4:00 pm — 5:31 pm AA1090 American Airlines Philadelphia — Chicago	5h 52m including layover	Find flight from$308
1:54 pm — 9:28 pm	1:54 pm — 3:29 pm AA4382 American Airlines Toronto — New York 4h 16m stop 7:45 pm — 9:28 pm AA417 American Airlines New York — Chicago	8h 34m including layover	Find flight from$180
1:54 pm — 8:33 pm	1:54 pm — 3:29 pm AA4382 American Airlines Toronto — New York 3h 21m stop 6:50 pm — 8:33 pm AA1263 American Airlines New York — Chicago	7h 39m including layover	Find flight from$180
3:50 pm — 8:33 pm	3:50 pm — 5:25 pm AA4556 American Airlines Toronto — New York 1h 25m stop 6:50 pm — 8:33 pm AA1263 American Airlines New York — Chicago	5h 43m including layover	Find flight from$179
3:50 pm — 9:28 pm	3:50 pm — 5:25 pm AA4556 American Airlines Toronto — New York 2h 20m stop 7:45 pm — 9:28 pm AA417 American Airlines New York — Chicago	6h 38m including layover	Find flight from$179
4:30 pm — 9:39 pm	4:30 pm — 6:39 pm AA5345 American Airlines Toronto — Charlotte 1h 51m stop 8:30 pm — 9:39 pm AA815 American Airlines Charlotte — Chicago	6h 9m including layover	Find flight from$179
4:30 pm — 0:05 am +1 day	4:30 pm — 6:39 pm AA5345 American Airlines Toronto — Charlotte 4h 17m stop 10:56 pm — 0:05 am AA1180 American Airlines Charlotte — Chicago	8h 35m including layover	Find flight from$180
5:15 pm — 10:05 pm	5:15 pm — 6:59 pm AA5667 American Airlines Toronto — Washington D.C. 1h 46m stop 8:45 pm — 10:05 pm AA1630 American Airlines Washington D.C. — Chicago	5h 50m including layover	Find flight from$179
6:00 am — 12:24 pm	6:00 am — 8:25 am AA5046 American Airlines Toronto — Charlotte 2h 48m stop 11:13 am — 12:24 pm AA2279 American Airlines Charlotte — Chicago	7h 24m including layover	Find flight from$180
7:00 am — 2:10 pm	7:00 am — 8:50 am AA4542 American Airlines Toronto — New York 1h 9m stop 9:59 am — 12:08 pm AA2036 American Airlines New York — Charlotte 52m stop 1:00 pm — 2:10 pm AA1052 American Airlines Charlotte — Chicago	8h 10m including layover	Find flight from$176
7:00 am — 3:40 pm	7:00 am — 8:50 am AA4542 American Airlines Toronto — New York 1h 9m stop 9:59 am — 12:08 pm AA2036 American Airlines New York — Charlotte 2h 24m stop 2:32 pm — 3:40 pm AA614 American Airlines Charlotte — Chicago	9h 40m including layover	Find flight from$176

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 12/21/2024

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 10:30 am to 7:35 am. Nonstop flight is 2h. The time difference between Toronto and Chicago is 1h.

The fastest flight 2h
Average flight time 2h
The earliest flight 10:30 am
The latest flight 7:35 am
Distance 436 ml

The cheapest months for traveling to Chicago are november (from 169 $).

The cheapest flight by American Airlines that our users were able to find is $169. This airfare is economy class on one-way AA3604 flight for November 12, 2024 leaving Pearson International in Toronto at 11:37 am, it includes all taxes and additional fees.

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American Airlines Airplanes on the Route

List of the most popular American Airlines airplanes flying from Toronto to Chicago:

Embraer 170

from $169

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Embraer 175 (short wing)

from $176

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Canadair Regional Jet 700

from $179

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Canadair Regional Jet 900

from $179

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Airbus A319

from $180

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Embraer RJ145

from $181

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Boeing 737-100/200

from $200

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Other Popular Airlines on the Route

Besides American Airlines there are other 7 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 19 direct flights every day from Toronto. Airlines and fares are below:

PD - Porter Airlines

from $122

Find
UA - United Airlines

from $168

Find
TS - Air Transat

from $153

Find

See more direct flights

Connecting Flights

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

AC - Air Canada

from $282

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PD - Porter Airlines

from $145

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WS - WestJet

from $168

Find
UA - United Airlines

from $173

Find
F8 - Freedom Airlines

from $203

Find
AY - Finnair

from $1381

Find
TS - Air Transat

from $168

Find

See more connecting flights

How to book an air ticket yourself?

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