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 $168 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 january: one-way - $168, two-way – $288.
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights
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
10:10 am — 12:55 pm
10:10 am — 11:38 am WS6413 WestJet
Toronto — Detroit
48m stop
12:26 pm — 12:55 pm WS7085 WestJet
Detroit — Chicago
3h 45m
including layover
Find flight
from$236
1:00 pm — 4:40 pm
1:00 pm — 2:22 pm WS6316 WestJet
Toronto — Detroit
1h 53m stop
4:15 pm — 4:40 pm WS7421 WestJet
Detroit — Chicago
4h 40m
including layover
Find flight
from$222
2:30 pm — 10:36 pm
7:55 am — 9:35 am WS6350 WestJet
Toronto — New York
4h 26m stop
8:55 pm — 10:43 pm WS7763 WestJet
New York — Chicago
9h 6m
including layover
Find flight
from$220
2:45 pm — 9:58 pm
2:45 pm — 4:17 pm WS6354 WestJet
Toronto — Minneapolis
4h 3m stop
8:20 pm — 9:58 pm WS8238 WestJet
Minneapolis — Chicago
8h 13m
including layover
Find flight
from$220
4:55 pm — 10:40 am
+1 day
4:55 pm — 8:12 pm WS1172 WestJet
Toronto — Fort Myers
12h 18m stop
8:30 am — 10:40 am NK570 Spirit Airlines
Fort Myers — Chicago
18h 45m
including layover
Find flight
from$173
4:55 pm — 3:33 pm
+1 day
4:55 pm — 8:12 pm WS1172 WestJet
Toronto — Fort Myers
17h 8m stop
1:20 pm — 3:33 pm NK528 Spirit Airlines
Fort Myers — Chicago
23h 38m
including layover
Find flight
from$192
5:15 pm — 8:53 pm
5:15 pm — 6:44 pm WS6338 WestJet
Toronto — Detroit
1h 36m stop
8:20 pm — 8:53 pm WS7570 WestJet
Detroit — Chicago
4h 38m
including layover
Find flight
from$212
6:15 am — 9:00 am
6:00 am — 7:41 am WS6342 WestJet
Toronto — Detroit
30m stop
8:40 am — 9:16 am WS7062 WestJet
Detroit — Chicago
3h 45m
including layover
Find flight
from$212
6:30 am — 10:43 am
6:30 am — 8:13 am WS6353 WestJet
Toronto — Minneapolis
52m stop
9:05 am — 10:43 am WS7776 WestJet
Minneapolis — Chicago
5h 13m
including layover
Find flight
from$212
7:45 am — 3:21 pm
7:45 am — 10:58 am WS1246 WestJet
Toronto — Tampa
2h 28m stop
1:26 pm — 3:21 pm F91185 Frontier Airlines
Tampa — Chicago
8h 36m
including layover
Find flight
from$175
7:45 am — 6:57 pm
7:45 am — 10:58 am WS1246 WestJet
Toronto — Tampa
5h 52m stop
4:50 pm — 6:57 pm NK572 Spirit Airlines
Tampa — Chicago
12h 12m
including layover
Find flight
from$175
10:45 pm — 11:44 am
+2 days
10:45 pm — 0:35 am WS535 WestJet
Toronto — Winnipeg
16h 25m stop
5:00 pm — 6:30 pm WS1352 WestJet
Winnipeg — Las Vegas
11h 41m stop
6:11 am — 11:44 am F92330 Frontier Airlines
Las Vegas — Chicago
37h 59m
including layover
Find flight
from$228
11:00 pm — 10:40 am
+2 days
11:00 pm — 0:10 am WS374 WestJet
Toronto — Ottawa
16h 10m stop
4:20 pm — 8:04 pm WS1262 WestJet
Ottawa — Fort Myers
12h 26m stop
8:30 am — 10:40 am NK570 Spirit Airlines
Fort Myers — Chicago
36h 40m
including layover
Find flight
from$203
11:00 pm — 12:39 pm
+2 days
11:00 pm — 0:10 am WS374 WestJet
Toronto — Ottawa
16h 10m stop
4:20 pm — 8:04 pm WS1262 WestJet
Ottawa — Fort Myers
14h 30m stop
10:34 am — 12:39 pm NK712 Spirit Airlines
Fort Myers — Chicago
38h 39m
including layover
Find flight
from$203
1:50 pm — 5:18 am
+1 day
1:50 pm — 4:17 pm WS661 WestJet
Toronto — Calgary
3h 3m stop
7:20 pm — 9:44 pm WS1512 WestJet
Calgary — Los Angeles
1h 31m stop
11:15 pm — 5:18 am NK1679 Spirit Airlines
Los Angeles — Chicago
16h 28m
including layover
Find flight
from$252
5:00 pm — 9:23 am
+1 day
5:00 pm — 7:28 pm WS719 WestJet
Toronto — Vancouver
3h 32m stop
11:00 pm — 6:53 am WS1598 WestJet
Vancouver — Atlanta
1h 32m stop
8:25 am — 9:23 am WS6556 WestJet
Atlanta — Chicago
17h 23m
including layover
Find flight
from$247
8:00 pm — 2:01 pm
+1 day
8:00 pm — 11:07 pm WS1166 WestJet
Toronto — Orlando
10h 10m stop
9:17 am — 11:52 am F92416 Frontier Airlines
Orlando — Philadelphia
48m stop
12:40 pm — 2:01 pm F91617 Frontier Airlines
Philadelphia — Chicago
19h 1m
including layover
Find flight
from$168
8:00 pm — 3:02 pm
+1 day
8:00 pm — 11:07 pm WS1166 WestJet
Toronto — Orlando
10h 10m stop
9:17 am — 11:52 am F92416 Frontier Airlines
Orlando — Philadelphia
1h 42m stop
1:34 pm — 3:02 pm F92111 Frontier Airlines
Philadelphia — Chicago
20h 2m
including layover
Find flight
from$168
*Departure and arrival times are local. Last updated on 12/22/2024

Flight Information

There are 77 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 10:05 pm to 8:35 am. Nonstop flight is 3h 45m. The time difference between Toronto and Chicago is 1h.

  • The fastest flight 3h 45m
  • Average flight time 19h 6m
  • The earliest flight 10:05 pm
  • The latest flight 8:35 am
  • Distance 436 ml

The cheapest months for traveling to Chicago are december (from 165 $), january (from 168 $), february (from 173 $).

The most expensive and popular months are november (from 221 $), february (from 173 $), january (from 168 $).

The cheapest flight by WestJet that our users were able to find is $168. This airfare is economy class on one-way WS1166 flight for January 12, 2025 leaving Pearson International in Toronto at 8:00 pm, it includes all taxes and additional fees.

Find same flight?

Other Popular Airlines on the Route

Besides WestJet 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 15 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