Air Canada Toronto to Chicago Flights

Return flight: Chicago – Toronto
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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Air Canada flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $399 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 january: one-way - $399, two-way – $684.
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Cheap Flights from Toronto to Chicago by Air Canada

Look at the list of plane tickets for the most connecting flights by Air Canada, their prices start from $399. There’re no direct flights. The fastest connecting flight – 5h 45m.
Price Departure Arrival Flight Time Airline Flight
from $399
Find flight
2:00 pm
Toronto
Pearson International
 6:45 pm
Chicago
O'Hare International
 5h 45m
layover
1h 27m - Montreal
 Air Canada
AC414
AC3653
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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 01/21/2025
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
2:00 pm — 6:45 pm
2:00 pm — 3:18 pm AC414 Air Canada
Toronto — Montreal
1h 27m stop
4:45 pm — 6:45 pm AC3653 Air Canada
Montreal — Chicago
5h 45m
including layover
Find flight
from$399
*Departure and arrival times are local. Last updated on 01/21/2025

Flight Information

There are 2 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 2:00 pm to 2:00 pm. Nonstop flight is 5h 45m. The time difference between Toronto and Chicago is 1h.

  • The fastest flight 5h 45m
  • Average flight time 5h 45m
  • The earliest flight 2:00 pm
  • The latest flight 2:00 pm
  • Distance 436 ml

The cheapest months for traveling to Chicago are february (from 399 $).

The cheapest flight by Air Canada that our users were able to find is $399. This airfare is economy class on one-way AC414 flight for February 21, 2025 leaving Pearson International in Toronto at 2:00 pm, 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:

Other Popular Airlines on the Route

Besides Air Canada there are other 6 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 10 direct flights every day from Toronto. Airlines and fares are below:

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Connecting Flights

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

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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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