Air Canada Toronto to Chicago Flights

Cheapflightsplus.com will find cheap Air Canada flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $101 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 june: one-way - $101, two-way – $173.
Direct flights
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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 Arrival Flight Details Flight Time Price
11:00 am — 12:01 pm
11:00 am — 12:01 pm AC4408 Air Canada
Toronto — Chicago
2h 1m
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from$161
12:10 pm — 1:04 pm
12:10 pm — 1:04 pm AC505 Air Canada
Toronto — Chicago
1h 54m
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from$153
1:00 pm — 2:01 pm
1:00 pm — 2:01 pm AC5588 Air Canada
Toronto — Chicago
2h 1m
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from$108
2:10 pm — 3:04 pm
2:10 pm — 3:04 pm AC507 Air Canada
Toronto — Chicago
1h 54m
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from$108
2:45 pm — 3:50 pm
2:45 pm — 3:50 pm AC5137 Air Canada
Toronto — Chicago
2h 5m
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from$153
4:30 pm — 5:24 pm
4:30 pm — 5:24 pm AC8909 Air Canada
Toronto — Chicago
1h 54m
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from$171
5:15 pm — 6:15 pm
5:15 pm — 6:15 pm AC4990 Air Canada
Toronto — Chicago
2h
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from$108
6:35 pm — 7:29 pm
6:35 pm — 7:29 pm AC511 Air Canada
Toronto — Chicago
1h 54m
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from$161
7:00 am — 7:59 am
7:00 am — 7:59 am AC5141 Air Canada
Toronto — Chicago
1h 59m
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from$108
8:15 am — 9:09 am
8:15 am — 9:09 am AC503 Air Canada
Toronto — Chicago
1h 54m
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from$153
8:15 am — 9:08 am
8:15 am — 9:08 am AC8901 Air Canada
Toronto — Chicago
1h 53m
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from$161
9:00 am — 9:59 am
9:00 am — 9:59 am AC5143 Air Canada
Toronto — Chicago
1h 59m
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from$108
9:00 pm — 10:05 pm
9:00 pm — 10:05 pm AC4961 Air Canada
Toronto — Chicago
2h 5m
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from$108
0:30 am — 7:55 am
0:30 am — 1:35 am AC472 Air Canada
Toronto — Ottawa
4h 58m stop
6:33 am — 7:55 am AC4103 Air Canada
Ottawa — Chicago
8h 25m
including layover
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from$182
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$123
11:15 pm — 7:55 am
+1 day
11:15 pm — 0:20 am AC470 Air Canada
Toronto — Ottawa
6h 13m stop
6:33 am — 7:55 am AC4103 Air Canada
Ottawa — Chicago
9h 40m
including layover
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from$129
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
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from$175
1:55 pm — 7:57 pm
1:55 pm — 3:32 pm AC1394 Air Canada
Toronto — Newark
2h 43m stop
6:15 pm — 7:57 pm AC5067 Air Canada
Newark — Chicago
7h 2m
including layover
Find flight
from$186
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$177
6:15 am — 11:24 am
6:15 am — 7:36 am AC480 Air Canada
Toronto — Montreal
2h 9m stop
9:45 am — 11:24 am AC3098 Air Canada
Montreal — Chicago
6h 9m
including layover
Find flight
from$106
6:15 am — 11:24 am
6:15 am — 7:36 am AC480 Air Canada
Toronto — Montreal
2h 9m stop
9:45 am — 11:24 am AC3532 Air Canada
Montreal — Chicago
6h 9m
including layover
Find flight
from$106
7:25 am — 11:24 am
7:25 am — 8:43 am AC7952 Air Canada
Toronto — Montreal
1h 2m stop
9:45 am — 11:24 am AC3098 Air Canada
Montreal — Chicago
4h 59m
including layover
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from$101
7:25 am — 11:24 am
7:25 am — 8:42 am AC7952 Air Canada
Toronto — Montreal
1h 3m stop
9:45 am — 11:24 am AC3532 Air Canada
Montreal — Chicago
4h 59m
including layover
Find flight
from$101
8:00 am — 2:47 pm
8:00 am — 9:21 am AC402 Air Canada
Toronto — Montreal
3h 54m stop
1:15 pm — 2:47 pm AC8963 Air Canada
Montreal — Chicago
7h 47m
including layover
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from$106
8:25 am — 2:47 pm
8:25 am — 9:42 am AC7954 Air Canada
Toronto — Montreal
3h 33m stop
1:15 pm — 2:47 pm AC8963 Air Canada
Montreal — Chicago
7h 22m
including layover
Find flight
from$101
9:00 am — 2:47 pm
9:00 am — 10:21 am AC404 Air Canada
Toronto — Montreal
2h 54m stop
1:15 pm — 2:47 pm AC8963 Air Canada
Montreal — Chicago
6h 47m
including layover
Find flight
from$106
10:25 am — 8:05 pm
10:25 am — 11:43 am AC7958 Air Canada
Toronto — Montreal
1h 42m stop
1:25 pm — 2:45 pm AC732 Air Canada
Montreal — New York
3h 45m stop
6:30 pm — 8:05 pm NK2178 Spirit Airlines
New York — Chicago
10h 40m
including layover
Find flight
from$190
11:15 pm — 11:24 am
+1 day
11:15 pm — 0:20 am AC470 Air Canada
Toronto — Ottawa
5h 40m stop
6:00 am — 6:46 am AC8002 Air Canada
Ottawa — Montreal
2h 59m stop
9:45 am — 11:24 am AC3098 Air Canada
Montreal — Chicago
13h 9m
including layover
Find flight
from$148
3:25 pm — 1:49 pm
+1 day
3:25 pm — 4:43 pm AC7968 Air Canada
Toronto — Montreal
2h 17m stop
7:00 pm — 9:55 pm AC1197 Air Canada
Montreal — Atlanta
14h 52m stop
12:47 pm — 1:49 pm F92291 Frontier Airlines
Atlanta — Chicago
23h 24m
including layover
Find flight
from$271
4:00 pm — 11:30 pm
4:00 pm — 5:05 pm AC460 Air Canada
Toronto — Ottawa
2h 24m stop
7:29 pm — 9:04 pm AC4694 Air Canada
Ottawa — Washington D.C.
1h 15m stop
10:19 pm — 11:30 pm AC4420 Air Canada
Washington D.C. — Chicago
8h 30m
including layover
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from$108
4:20 pm — 11:30 pm
4:20 pm — 5:17 pm AC7710 Air Canada
Toronto — Ottawa
2h 12m stop
7:29 pm — 9:04 pm AC4694 Air Canada
Ottawa — Washington D.C.
1h 15m stop
10:19 pm — 11:30 pm AC4420 Air Canada
Washington D.C. — Chicago
8h 10m
including layover
Find flight
from$103
5:25 pm — 6:37 am
+1 day
5:25 pm — 6:43 pm AC7972 Air Canada
Toronto — Montreal
1h 17m stop
8:00 pm — 9:47 pm AC8898 Air Canada
Montreal — Newark
7h 13m stop
5:00 am — 6:37 am NK2543 Spirit Airlines
Newark — Chicago
14h 12m
including layover
Find flight
from$215
*Departure and arrival times are local. Last updated on 06/03/2025

Flight Information

There are 13 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 0:30 am to 9:00 pm. Nonstop flight is 1h 53m. The time difference between Toronto and Chicago is 1h.

  • The fastest flight 1h 53m
  • Average flight time 1h 59m
  • The earliest flight 0:30 am
  • The latest flight 9:00 pm
  • Distance 436 ml

The cheapest months for traveling to Chicago are june (from 135 $), august (from 164 $), may (from 194 $).

The most expensive and popular months are november (from 866 $), july (from 222 $), may (from 194 $).

The cheapest flight by Air Canada that our users were able to find is $101. This airfare is economy class on one-way AC7952 flight for June 29, 2025 leaving Toronto Island in Toronto at 7:25 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides Air Canada there are other 10 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 39 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):

  • from $129
    Find
  • from $84
    Find
  • F8 - Freedom Airlines
    from $120
    Find
  • AS - Alaska Airlines
    from $218
    Find
  • AV - Avianca
    from $408
    Find
  • SY - Sun Country Airlines
    from $162
    Find
  • WS - WestJet
    from $132
    Find
  • AM - Aeromexico
    from $498
    Find
  • LX - SWISS International Air Lines
    from $3152
    Find
  • TS - Air Transat
    from $146
    Find
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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