WestJet Calgary to Chicago Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap WestJet flights from Calgary to Chicago. Compare airline ticket prices and book air tickets starting from $153 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of WestJet, arrivals and departure details below.

Find Cheap Airfare Calgary (AB) — 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 march: one-way - $153, two-way – $262.

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Cheap Flights from Calgary to Chicago by WestJet

Look at the list of plane tickets for the most connecting flights by WestJet, their prices start from $153. There’re no direct flights. The fastest connecting flight – 8h 6m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $161 Find flight	7:10 pm Calgary Calgary Int.	10:42 am+1 день Chicago Midway	14h 32m layover 7h 56m - Phoenix	WestJet	WS1536 F91736
from $173 Find flight	9:55 am Calgary Calgary Int.	8:49 pm Chicago Midway	9h 54m layover 3h 35m - Atlanta	WestJet	WS1590 F92779
from $213 Find flight	0:30 am Calgary Calgary Int.	10:55 am Chicago Midway	9h 25m layover 3h 6m - Atlanta	WestJet	WS1992 F92143
from $224 Find flight	8:00 am Calgary Calgary Int.	1:52 am+1 день Chicago O'Hare International	16h 52m layover 9h 56m - Phoenix	WestJet	WS1394 F91828
from $250 Find flight	3:15 pm Calgary Calgary Int.	1:52 am+1 день Chicago O'Hare International	9h 37m layover 2h 42m - Phoenix	WestJet	WS1492 F91828
from $153 Find flight	9:45 pm Calgary Calgary Int.	8:49 pm+1 день Chicago Midway	22h 4m layover 1h 58m - Edmonton 12h 48m - Atlanta	WestJet	WS289 WS1940 F92779
from $186 Find flight	6:55 pm Calgary Calgary Int.	10:39 am+1 день Chicago O'Hare International	14h 44m layover 3h 58m - Las Vegas 2h 16m - Dallas	WestJet	WS1400 F91650 F93242
from $226 Find flight	9:20 am Calgary Calgary Int.	4:47 am+1 день Chicago O'Hare International	18h 27m layover 8h 55m - San Diego 0h 44m - Las Vegas	WestJet	WS1564 F91470 F92146
from $226 Find flight	9:20 am Calgary Calgary Int.	6:33 am+1 день Chicago Midway	20h 13m layover 8h 55m - San Diego 2h 44m - Las Vegas	WestJet	WS1564 F91470 F92330
from $227 Find flight	11:20 pm Calgary Calgary Int.	1:59 am+2 дня Chicago O'Hare International	25h 39m layover 9h 14m - Vancouver 7h 54m - Phoenix	WestJet	WS135 WS1770 F91828
from $229 Find flight	8:00 am Calgary Calgary Int.	9:13 am+1 день Chicago Midway	24h 13m layover 12h 42m - Phoenix 0h 55m - Orlando	WestJet	WS1394 F91086 F91457
from $229 Find flight	8:00 am Calgary Calgary Int.	1:03 am+1 день Chicago O'Hare International	16h 3m layover 5h 7m - Phoenix 3h 6m - Denver	WestJet	WS1394 F92106 F93172
from $232 Find flight	11:00 am Calgary Calgary Int.	10:39 am+1 день Chicago O'Hare International	22h 39m layover 11h 16m - San Francisco 2h 2m - Dallas	WestJet	WS1508 F94000 F93242
from $232 Find flight	11:20 pm Calgary Calgary Int.	6:33 am+2 дня Chicago Midway	30h 13m layover 17h 29m - Vancouver 4h 43m - Las Vegas	WestJet	WS135 WS1790 F92330
from $237 Find flight	11:40 pm Calgary Calgary Int.	11:59 pm+1 день Chicago O'Hare International	23h 19m layover 9h 7m - Kelowna 8h 3m - Seattle	WestJet	WS279 WS3750 AS538
from $241 Find flight	9:35 am Calgary Calgary Int.	1:52 am+1 день Chicago O'Hare International	15h 17m layover 4h 57m - Los Angeles 1h 42m - Phoenix	WestJet	WS1510 F93304 F91828

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 02/22/2025

WestJet Flight Schedule Calgary to Chicago

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	Flight Details	Flight Time	Price
0:30 am — 10:55 am	0:30 am — 6:52 am WS1992 WestJet Calgary — Atlanta 3h 6m stop 4:12 pm — 5:12 pm F92143 Frontier Airlines Atlanta — Chicago	9h 25m including layover	Find flight from$213
0:30 am — 4:31 pm	0:30 am — 6:54 am WS1992 WestJet Calgary — Atlanta 8h 29m stop 3:23 pm — 4:31 pm F91595 Frontier Airlines Atlanta — Chicago	15h 1m including layover	Find flight from$228
3:15 pm — 1:52 am +1 day	3:15 pm — 6:29 pm WS1492 WestJet Calgary — Phoenix 2h 42m stop 9:11 pm — 1:52 am F91828 Frontier Airlines Phoenix — Chicago	9h 37m including layover	Find flight from$250
6:55 pm — 6:33 am +1 day	6:55 pm — 8:51 pm WS1400 WestJet Calgary — Las Vegas 4h 5m stop 6:50 am — 12:34 pm F92330 Frontier Airlines Las Vegas — Chicago	10h 38m including layover	Find flight from$224
7:10 pm — 10:42 am +1 day	7:10 pm — 10:22 pm WS1536 WestJet Calgary — Phoenix 7h 56m stop 4:28 pm — 8:47 pm F91736 Frontier Airlines Phoenix — Chicago	14h 32m including layover	Find flight from$161
8:00 am — 1:52 am +1 day	8:00 am — 11:15 am WS1394 WestJet Calgary — Phoenix 9h 56m stop 9:11 pm — 1:52 am F91828 Frontier Airlines Phoenix — Chicago	16h 52m including layover	Find flight from$224
11:00 am — 10:39 am +1 day	11:00 am — 1:06 pm WS1508 WestJet Calgary — San Francisco 11h 16m stop 0:22 am — 5:58 am F94000 Frontier Airlines San Francisco — Dallas 2h 2m stop 8:00 am — 10:39 am F93242 Frontier Airlines Dallas — Chicago	22h 39m including layover	Find flight from$232
11:20 pm — 1:59 am +2 days	11:20 pm — 0:01 am WS135 WestJet Calgary — Vancouver 9h 14m stop 9:15 am — 1:24 pm WS1770 WestJet Vancouver — Phoenix 7h 54m stop 9:18 pm — 1:59 am F91828 Frontier Airlines Phoenix — Chicago	25h 39m including layover	Find flight from$227
12:30 pm — 9:55 pm	12:30 pm — 3:35 pm WS738 WestJet Calgary — Winnipeg 2h 3m stop 5:45 pm — 7:20 pm WS6853 WestJet Winnipeg — Minneapolis 1h 12m stop 8:45 pm — 10:14 pm WS8238 WestJet Minneapolis — Chicago	8h 25m including layover	Find flight from$306
2:30 pm — 9:08 am +1 day	2:30 pm — 4:54 pm WS1514 WestJet Calgary — Los Angeles 5h 37m stop 10:31 pm — 6:04 am F93216 Frontier Airlines Los Angeles — Atlanta 1h 56m stop 8:00 am — 9:08 am F91441 Frontier Airlines Atlanta — Chicago	17h 38m including layover	Find flight from$241
2:35 pm — 4:47 am +1 day	2:35 pm — 3:36 pm WS3135 WestJet Calgary — Edmonton 1h 39m stop 5:15 pm — 7:25 pm WS1450 WestJet Edmonton — Las Vegas 3h 34m stop 10:59 pm — 4:47 am F92146 Frontier Airlines Las Vegas — Chicago	13h 12m including layover	Find flight from$262
3:15 pm — 6:33 am +1 day	3:15 pm — 6:27 pm WS1492 WestJet Calgary — Phoenix 2h 36m stop 9:59 pm — 10:13 pm F94113 Frontier Airlines Phoenix — Las Vegas 3h 35m stop 6:11 am — 11:48 am F92330 Frontier Airlines Las Vegas — Chicago	14h 18m including layover	Find flight from$190
6:55 pm — 10:39 am +1 day	6:55 pm — 8:51 pm WS1400 WestJet Calgary — Las Vegas 3h 58m stop 0:59 am — 5:48 am F91650 Frontier Airlines Las Vegas — Dallas 2h 16m stop 9:05 am — 11:26 am F93242 Frontier Airlines Dallas — Chicago	14h 44m including layover	Find flight from$186
7:10 pm — 3:53 pm +1 day	7:10 pm — 10:24 pm WS1536 WestJet Calgary — Phoenix 10h 6m stop 8:30 am — 11:57 am F92532 Frontier Airlines Phoenix — Dallas 1h 34m stop 1:31 pm — 3:53 pm F91888 Frontier Airlines Dallas — Chicago	19h 43m including layover	Find flight from$207
8:00 am — 9:13 am +1 day	8:00 am — 11:15 am WS1394 WestJet Calgary — Phoenix 12h 42m stop 11:57 pm — 6:30 am F91086 Frontier Airlines Phoenix — Orlando 55m stop 7:25 am — 9:13 am F91457 Frontier Airlines Orlando — Chicago	24h 13m including layover	Find flight from$229
9:45 pm — 8:49 pm +1 day	9:45 pm — 10:49 pm WS289 WestJet Calgary — Edmonton 1h 58m stop 0:45 am — 7:06 am WS1940 WestJet Edmonton — Atlanta 12h 48m stop 10:28 pm — 11:29 pm F92779 Frontier Airlines Atlanta — Chicago	22h 4m including layover	Find flight from$153
9:45 pm — 10:55 am +1 day	9:45 pm — 10:49 pm WS289 WestJet Calgary — Edmonton 1h 58m stop 0:45 am — 7:06 am WS1940 WestJet Edmonton — Atlanta 2h 54m stop 4:12 pm — 5:12 pm F92143 Frontier Airlines Atlanta — Chicago	12h 10m including layover	Find flight from$162

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 02/22/2025

Flight Information

There are 53 flights by WestJet from Calgary to Chicago every week with departures from Calgary Int.. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 0:20 am to 9:55 am. Nonstop flight is 8h 6m. The time difference between Calgary and Chicago is 1h.

The fastest flight 8h 6m
Average flight time 14h 52m
The earliest flight 0:20 am
The latest flight 9:55 am
Distance 1398 ml

The cheapest months for traveling to Chicago are january (from 153 $), february (from 155 $), december (from 162 $).

The most expensive and popular months are november (from 184 $), december (from 162 $), february (from 155 $).

The cheapest flight by WestJet that our users were able to find is $153. This airfare is economy class on one-way WS289 flight for February 21, 2025 leaving Calgary Int. in Calgary at 9:45 pm, it includes all taxes and additional fees.

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WestJet Airplanes on the Route

List of the most popular WestJet airplanes flying from Calgary to Chicago:

Other Popular Airlines on the Route

Besides WestJet there are other 3 airline carriers between Calgary and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Calgary to Chicago.

Nonstop flights

There are 1 direct flights every day from Calgary. Airlines and fares are below:

UA - United Airlines

from $310

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Connecting Flights

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

AS - Alaska Airlines

from $335

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UA - United Airlines

from $314

Find
F8 - Freedom Airlines

from $266

Find

See more connecting flights

How to book an air ticket yourself?

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