Air Canada Toronto to Chicago Flights

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Cheapflightsplus.com will find cheap Air Canada flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $167 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Air Canada, arrivals and departure details below.

Find Cheap Airfare Toronto (ON) — Chicago (IL) by Air Canada

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 july: one-way - $167, two-way – $286.

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Cheap Flights from Toronto to Chicago by Air Canada

Look at the list of plane tickets for the most popular direct and connecting flights by Air Canada, their prices start from $167. The fastest nonstop flight takes 2h. The fastest connecting flight — 5h 51m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $389 Find flight	5:15 pm Toronto Pearson International	6:15 pm Chicago O'Hare International	2h 0m	Air Canada	AC4990
from $389 Find flight	1:00 pm Toronto Pearson International	2:01 pm Chicago O'Hare International	2h 1m	Air Canada	AC5588
from $389 Find flight	2:45 pm Toronto Pearson International	3:50 pm Chicago O'Hare International	2h 5m	Air Canada	AC5137
from $167 Find flight	10:20 am Toronto Toronto Island	6:53 pm Chicago O'Hare International	9h 33m layover 6h 8m - Ottawa	Air Canada	AC7706 AC3553
from $238 Find flight	12:25 pm Toronto Toronto Island	8:16 pm Chicago O'Hare International	8h 51m layover 4h 57m - Montreal	Air Canada	AC7962 AC8965
from $240 Find flight	3:25 pm Toronto Toronto Island	8:16 pm Chicago O'Hare International	5h 51m layover 1h 57m - Montreal	Air Canada	AC7968 AC8965
from $418 Find flight	2:00 pm Toronto Pearson International	6:53 pm Chicago O'Hare International	5h 53m layover 2h 20m - Ottawa	Air Canada	AC456 AC3553
from $421 Find flight	11:20 pm Toronto Pearson International	10:46 pm+1 день Chicago O'Hare International	24h 26m layover 7h 29m - Montreal 5h 17m - Los Angeles	Air Canada	AC432 AC775 F92446
from $519 Find flight	11:20 pm Toronto Pearson International	10:55 am+2 дня Chicago O'Hare International	36h 35m layover 18h 34m - Montreal 6h 55m - Mexico City	Air Canada	AC432 AC995 VB186
from $548 Find flight	11:20 pm Toronto Pearson International	11:32 pm+2 дня Chicago O'Hare International	49h 12m layover 18h 34m - Montreal 19h 35m - Mexico City	Air Canada	AC432 AC995 Y4702
from $661 Find flight	11:20 pm Toronto Pearson International	3:27 pm+2 дня Chicago O'Hare International	41h 7m layover 8h 19m - Montreal 24h 52m - Orlando	Air Canada	AC432 AC1634 F93043
from $726 Find flight	11:20 pm Toronto Pearson International	9:16 pm+1 день Chicago O'Hare International	22h 56m layover 8h 19m - Montreal 3h 43m - Punta Cana	Air Canada	AC432 AC1790 F981
from $1066 Find flight	11:20 pm Toronto Pearson International	2:25 pm+2 дня Chicago O'Hare International	40h 5m layover 18h 34m - Montreal 9h 55m - Mexico City	Air Canada	AC432 AC995 AM686

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 07/10/2025

Air Canada 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
10:20 am — 6:53 pm	10:20 am — 11:17 am AC7706 Air Canada Toronto — Ottawa 6h 8m stop 5:25 pm — 6:53 pm AC3553 Air Canada Ottawa — Chicago	9h 33m including layover	Find flight from$167
11:20 pm — 10:46 pm +1 day	11:20 pm — 0:41 am AC432 Air Canada Toronto — Montreal 7h 29m stop 8:05 am — 11:02 am AC775 Air Canada Montreal — Los Angeles 5h 17m stop 4:24 pm — 10:46 pm F92446 Frontier Airlines Los Angeles — Chicago	24h 26m including layover	Find flight from$421
11:20 pm — 10:55 am +2 days	11:20 pm — 0:41 am AC432 Air Canada Toronto — Montreal 18h 34m stop 7:15 pm — 10:55 pm AC995 Air Canada Montreal — Mexico City 6h 55m stop 5:50 am — 10:55 am VB186 VivaAerobus Mexico City — Chicago	36h 35m including layover	Find flight from$519
11:20 pm — 11:32 pm +2 days	11:20 pm — 0:41 am AC432 Air Canada Toronto — Montreal 18h 34m stop 7:15 pm — 10:55 pm AC995 Air Canada Montreal — Mexico City 19h 35m stop 6:30 pm — 11:32 pm Y4702 Volaris Mexico City — Chicago	49h 12m including layover	Find flight from$548
11:20 pm — 3:27 pm +2 days	11:20 pm — 0:41 am AC432 Air Canada Toronto — Montreal 8h 19m stop 9:00 am — 12:14 pm AC1634 Air Canada Montreal — Orlando 24h 52m stop 1:06 pm — 3:27 pm F93043 Frontier Airlines Orlando — Chicago	41h 7m including layover	Find flight from$661
11:20 pm — 9:16 pm +1 day	11:20 pm — 0:41 am AC432 Air Canada Toronto — Montreal 8h 19m stop 9:00 am — 1:25 pm AC1790 Air Canada Montreal — Punta Cana 3h 43m stop 5:08 pm — 9:16 pm F981 Frontier Airlines Punta Cana — Chicago	22h 56m including layover	Find flight from$726
11:20 pm — 2:25 pm +2 days	11:20 pm — 0:41 am AC432 Air Canada Toronto — Montreal 18h 34m stop 7:15 pm — 10:55 pm AC995 Air Canada Montreal — Mexico City 9h 55m stop 8:50 am — 2:25 pm AM686 Aeromexico Mexico City — Chicago	40h 5m including layover	Find flight from$1066
12:25 pm — 8:16 pm	12:25 pm — 1:43 pm AC7962 Air Canada Toronto — Montreal 4h 57m stop 6:40 pm — 8:16 pm AC8965 Air Canada Montreal — Chicago	8h 51m including layover	Find flight from$238
1:00 pm — 2:01 pm	1:00 pm — 2:01 pm AC5588 Air Canada Toronto — Chicago	2h 1m	Find flight from$389
2:00 pm — 6:53 pm	2:00 pm — 3:05 pm AC456 Air Canada Toronto — Ottawa 2h 20m stop 5:25 pm — 6:53 pm AC3553 Air Canada Ottawa — Chicago	5h 53m including layover	Find flight from$418
2:45 pm — 3:50 pm	2:45 pm — 3:50 pm AC5137 Air Canada Toronto — Chicago	2h 5m	Find flight from$389
3:25 pm — 8:16 pm	3:25 pm — 4:43 pm AC7968 Air Canada Toronto — Montreal 1h 57m stop 6:40 pm — 8:16 pm AC8965 Air Canada Montreal — Chicago	5h 51m including layover	Find flight from$240
5:15 pm — 6:15 pm	5:15 pm — 6:15 pm AC4990 Air Canada Toronto — Chicago	2h	Find flight from$389

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

*Departure and arrival times are local. Last updated on 07/10/2025

Flight Information

There are 3 flights by Air Canada 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 10:20 am to 5:15 pm. Nonstop flight is 2h. The time difference between Toronto and Chicago is 1h.

The fastest flight 2h
Average flight time 2h 1m
The earliest flight 10:20 am
The latest flight 5:15 pm
Distance 436 ml

The cheapest months for traveling to Chicago are june (from 147 $), august (from 167 $), may (from 207 $).

The most expensive and popular months are november (from 879 $), july (from 389 $), may (from 207 $).

The cheapest flight by Air Canada that our users were able to find is $167. This airfare is economy class on one-way AC7706 flight for August 15, 2025 leaving Toronto Island in Toronto at 10:20 am, it includes all taxes and additional fees.

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Air Canada Airplanes on the Route

List of the most popular Air Canada airplanes flying from Toronto to Chicago:

Embraer 175

from $389

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Other Popular Airlines on the Route

Besides Air Canada there are other 9 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 27 direct flights every day from Toronto. Airlines and fares are below:

PD - Porter Airlines

from $75

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UA - United Airlines

from $98

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TS - Air Transat

from $119

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Connecting Flights

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

PD - Porter Airlines

from $175

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UA - United Airlines

from $114

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F8 - Freedom Airlines

from $163

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AV - Avianca

from $602

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SY - Sun Country Airlines

from $219

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WS - WestJet

from $188

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AM - Aeromexico

from $674

Find
LX - SWISS International Air Lines

from $4268

Find
TS - Air Transat

from $198

Find

See more connecting flights

How to book an air ticket yourself?

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