WestJet Toronto to Chicago Flights

Cheapflightsplus.com will find cheap WestJet flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $217 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of WestJet, arrivals and departure details below.

Find Cheap Airfare Toronto (ON) — Chicago (IL) by WestJet

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 december: one-way - $217, two-way – $372.
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights
Below is a detailed 2022 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
11:15 pm — 8:30 am
+1 day
11:15 pm — 0:19 am WS374 WestJet
Toronto — Ottawa
7h stop
7:19 am — 8:30 am UA6000 United Airlines
Ottawa — Chicago
10h 15m
including layover
Find flight
from$351
12:25 pm — 6:55 pm
12:25 pm — 1:56 pm WS1206 WestJet
Toronto — New York
3h 19m stop
5:15 pm — 6:55 pm DL7896 Delta Air Lines Inc.
New York — Chicago
7h 30m
including layover
Find flight
from$265
1:42 pm — 7:04 pm
1:42 pm — 2:57 pm WS6344 WestJet
Toronto — Minneapolis
2h 33m stop
5:30 pm — 7:04 pm WS7846 WestJet
Minneapolis — Chicago
6h 22m
including layover
Find flight
from$306
2:35 pm — 7:58 pm
2:35 pm — 4:06 pm WS1208 WestJet
Toronto — New York
2h 9m stop
6:15 pm — 7:58 pm WS7725 WestJet
New York — Chicago
6h 23m
including layover
Find flight
from$308
4:15 pm — 9:45 pm
4:15 pm — 5:46 pm WS1210 WestJet
Toronto — New York
2h 14m stop
8:00 pm — 9:45 pm WS7915 WestJet
New York — Chicago
6h 30m
including layover
Find flight
from$308
5:30 pm — 9:45 pm
5:30 pm — 7:01 pm WS1212 WestJet
Toronto — New York
59m stop
8:00 pm — 9:45 pm WS7915 WestJet
New York — Chicago
5h 15m
including layover
Find flight
from$308
6:25 am — 7:04 pm
6:25 am — 7:38 am WS6348 WestJet
Toronto — Minneapolis
9h 52m stop
5:30 pm — 7:04 pm WS7846 WestJet
Minneapolis — Chicago
13h 39m
including layover
Find flight
from$223
7:05 am — 12:55 pm
7:05 am — 8:36 am WS1200 WestJet
Toronto — New York
2h 39m stop
11:15 am — 12:55 pm WS7888 WestJet
New York — Chicago
6h 50m
including layover
Find flight
from$223
8:25 pm — 8:53 am
+1 day
8:25 pm — 9:56 pm WS1216 WestJet
Toronto — New York
9h 19m stop
7:15 am — 8:53 am WS7912 WestJet
New York — Chicago
13h 28m
including layover
Find flight
from$308
9:45 am — 8:03 pm
9:45 am — 12:30 pm WS1228 WestJet
Toronto — Orlando
5h 29m stop
5:59 pm — 8:03 pm NK912 Spirit Airlines
Orlando — Chicago
11h 18m
including layover
Find flight
from$217
10:00 pm — 9:48 am
+1 day
10:00 pm — 11:08 pm WS3478 WestJet
Toronto — Ottawa
6h 52m stop
6:00 am — 6:45 am AC8970 Air Canada
Ottawa — Montreal
1h 35m stop
8:20 am — 9:48 am AC7591 Air Canada
Montreal — Chicago
12h 48m
including layover
Find flight
from$298
*Departure and arrival times are local. Last updated on 11/29/2022

Flight Information

There are 83 flights by WestJet 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 10:00 pm to 9:45 am. Nonstop flight is 3h 19m. The time difference between Toronto and Chicago is 1h.

  • The fastest flight 3h 19m
  • Average flight time 9h 57m
  • The earliest flight 10:00 pm
  • The latest flight 9:45 am
  • Distance 436 ml

The cheapest flight by WestJet that our users were able to find is $217. This airfare is economy class on one-way WS1228 flight for October 3, 2018 leaving Pearson International in Toronto at 9:45 am, it includes all taxes and additional fees.

Find same flight?

Other Popular Airlines on the Route

Besides WestJet 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 50 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):

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.

Back