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 $104 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 - $104, two-way – $178.

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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 $104. The fastest nonstop flight takes 1h 52m. The fastest connecting flight — 4h 55m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $107 Find flight	8:15 am Toronto Pearson International	9:07 am Chicago O'Hare International	1h 52m	American Airlines	AA3430
from $109 Find flight	11:45 am Toronto Pearson International	12:37 pm Chicago O'Hare International	1h 52m	American Airlines	AA4003
from $109 Find flight	3:14 pm Toronto Pearson International	4:06 pm Chicago O'Hare International	1h 52m	American Airlines	AA3291
from $109 Find flight	8:16 am Toronto Pearson International	9:11 am Chicago O'Hare International	1h 55m	American Airlines	AA2520
from $109 Find flight	7:55 pm Toronto Pearson International	8:48 pm Chicago O'Hare International	1h 53m	American Airlines	AA3231
from $109 Find flight	6:21 pm Toronto Pearson International	7:16 pm Chicago O'Hare International	1h 55m	American Airlines	AA4112

from $109 Find flight	3:14 pm Toronto Pearson International	4:06 pm Chicago O'Hare International	1h 52m	American Airlines	AA3080
from $109 Find flight	6:21 pm Toronto Pearson International	7:16 pm Chicago O'Hare International	1h 55m	American Airlines	AA3526
from $109 Find flight	7:55 pm Toronto Pearson International	8:48 pm Chicago O'Hare International	1h 53m	American Airlines	AA3033
from $109 Find flight	11:45 am Toronto Pearson International	12:37 pm Chicago O'Hare International	1h 52m	American Airlines	AA3736
from $104 Find flight	7:00 am Toronto Pearson International	10:57 am Chicago O'Hare International	4h 57m layover 0h 47m - Philadelphia	American Airlines	AA4992 AA2095
from $104 Find flight	7:15 pm Toronto Pearson International	11:45 pm Chicago O'Hare International	5h 30m layover 1h 14m - Charlotte	American Airlines	AA5139 AA483
from $104 Find flight	6:30 am Toronto Pearson International	11:23 pm Chicago O'Hare International	17h 53m layover 13h 43m - New York	American Airlines	AA3955 AA222

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 02/27/2021

American Airlines Flight Schedule Toronto to Chicago

Below is a detailed 2021 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
11:45 am — 12:37 pm	11:45 am — 12:37 pm AA4003 American Airlines Toronto — Chicago	1h 52m	Find flight from$109
3:14 pm — 4:06 pm	3:14 pm — 4:06 pm AA3291 American Airlines Toronto — Chicago	1h 52m	Find flight from$109
6:21 pm — 7:16 pm	6:21 pm — 7:16 pm AA4112 American Airlines Toronto — Chicago	1h 55m	Find flight from$109
7:55 pm — 8:48 pm	7:55 pm — 8:48 pm AA3231 American Airlines Toronto — Chicago	1h 53m	Find flight from$109
8:15 am — 9:07 am	8:15 am — 9:07 am AA3430 American Airlines Toronto — Chicago	1h 52m	Find flight from$107
10:57 am — 5:41 pm	10:57 am — 12:25 pm AA4864 American Airlines Toronto — Philadelphia 3h 35m stop 4:00 pm — 5:41 pm AA1941 American Airlines Philadelphia — Chicago	7h 44m including layover	Find flight from$105
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	Find flight from$109
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	Find flight from$142
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	Find flight from$109
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	Find flight from$104
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	Find flight from$104
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	Find flight from$109
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	Find flight from$104
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	Find flight from$104
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	Find flight from$109
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	Find flight from$109

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

*Departure and arrival times are local. Last updated on 02/27/2021

Flight Information

There are 17 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 55m
The earliest flight 10:25 am
The latest flight 9:15 am
Distance 436 ml

The cheapest months for traveling to Chicago are september (from 105 $), november (from 106 $), october (from 106 $).

The most expensive and popular months are august (from 136 $), october (from 106 $), november (from 106 $).

The cheapest flight by American Airlines that our users were able to find is $104. 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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American Airlines Airplanes on the Route

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

Embraer RJ145

from $104

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Airbus A319

from $104

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Bombardier CRJ 900

from $104

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Embraer RJ140

from $104

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Embraer 175 (short wing)

from $107

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Canadair Regional Jet

from $109

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Canadair Regional Jet 700

from $109

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Boeing 737-800

from $109

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Embraer 175

from $109

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Bombardier CRJ 700

from $109

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

AC - Air Canada

from $98

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PD - Porter Airlines

from $106

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UA - United Airlines

from $101

Find

See more direct flights

Connecting Flights

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

AC - Air Canada

from $89

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DL - Delta Air Lines Inc.

from $127

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UA - United Airlines

from $106

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WS - WestJet

from $213

Find

See more connecting flights

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.