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 $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.
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
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 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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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:

See more direct flights

Connecting Flights

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

  • from $175
    Find
  • from $114
    Find
  • F8 - Freedom Airlines
    from $163
    Find
  • AV - Avianca
    from $602
    Find
  • SY - Sun Country Airlines
    from $219
    Find
  • WS - WestJet
    from $188
    Find
  • 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?

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.

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