WestJet Calgary to Chicago Flights

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Cheapflightsplus.com will find cheap WestJet flights from Calgary to Chicago. Compare airline ticket prices and book air tickets starting from $169 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 april: one-way - $169, two-way – $290.

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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 $169. There’re no direct flights. The fastest connecting flight – 5h 14m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $177 Find flight	3:15 pm Calgary Calgary Int.	10:02 pm+1 день Chicago Midway	29h 47m layover 23h 17m - Phoenix	WestJet	WS1492 F91736
from $179 Find flight	8:00 am Calgary Calgary Int.	7:45 pm Chicago O'Hare International	10h 45m layover 4h 4m - Phoenix	WestJet	WS1394 F91830
from $183 Find flight	9:55 am Calgary Calgary Int.	11:47 pm Chicago O'Hare International	12h 52m layover 6h 12m - Atlanta	WestJet	WS1590 F91441
from $192 Find flight	9:55 am Calgary Calgary Int.	8:49 pm Chicago Midway	9h 54m layover 3h 35m - Atlanta	WestJet	WS1590 F92779
from $204 Find flight	7:10 pm Calgary Calgary Int.	11:40 am+1 день Chicago O'Hare International	15h 30m layover 8h 43m - Phoenix	WestJet	WS1536 F91828
from $236 Find flight	0:30 am Calgary Calgary Int.	10:55 am Chicago Midway	9h 25m layover 3h 6m - Atlanta	WestJet	WS1992 F92143
from $169 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 $170 Find flight	8:00 pm Calgary Calgary Int.	11:24 pm+1 день Chicago Midway	26h 24m layover 3h 41m - Edmonton 15h 17m - Atlanta	WestJet	WS3137 WS1940 F92779
from $182 Find flight	8:00 pm Calgary Calgary Int.	11:47 pm+1 день Chicago O'Hare International	26h 47m layover 3h 41m - Edmonton 15h 23m - Atlanta	WestJet	WS3137 WS1940 F91441
from $184 Find flight	1:10 pm Calgary Calgary Int.	11:48 am+1 день Chicago Midway	21h 38m layover 3h 3m - Phoenix 10h 31m - Las Vegas	WestJet	WS1410 F94113 F92330
from $185 Find flight	9:55 am Calgary Calgary Int.	4:06 pm+1 день Chicago O'Hare International	29h 11m layover 13h 13m - Atlanta 6h 18m - Miami	WestJet	WS1590 NK3176 NK157
from $190 Find flight	8:40 am Calgary Calgary Int.	10:55 am+1 день Chicago O'Hare International	25h 15m layover 0h 36m - Regina 19h 23m - Minneapolis	WestJet	WS274 WS3758 SY259
from $190 Find flight	9:55 am Calgary Calgary Int.	11:41 am+1 день Chicago Midway	24h 46m layover 2h 10m - Atlanta 13h 54m - Tampa	WestJet	WS1590 F93054 F91185
from $191 Find flight	6:50 am Calgary Calgary Int.	8:14 pm Chicago Midway	12h 24m layover 1h 39m - Vancouver 2h 33m - Phoenix	WestJet	WS101 WS1770 F91736
from $191 Find flight	6:50 am Calgary Calgary Int.	10:22 pm Chicago Midway	14h 32m layover 1h 39m - Vancouver 4h 43m - Phoenix	WestJet	WS101 WS1770 F91738
from $195 Find flight	0:30 am Calgary Calgary Int.	0:20 am+1 день Chicago Midway	22h 50m layover 10h 28m - Atlanta 3h 32m - Philadelphia	WestJet	WS1992 F92298 F94367

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 04/11/2025

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 — 9:29 pm	0:30 am — 6:52 am WS1992 WestJet Calgary — Atlanta 13h 31m stop 8:23 pm — 9:29 pm F92779 Frontier Airlines Atlanta — Chicago	19h 59m including layover	Find flight from$192
10:30 am — 9:37 pm	10:30 am — 12:29 pm WS1424 WestJet Calgary — Las Vegas 3h 26m stop 3:55 pm — 9:37 pm F91944 Frontier Airlines Las Vegas — Chicago	10h 7m including layover	Find flight from$517
12:20 pm — 10:42 pm	12:20 pm — 5:29 pm WS1572 WestJet Calgary — Houston 2h 45m stop 8:54 pm — 11:25 pm F93282 Frontier Airlines Houston — Chicago	9h 22m including layover	Find flight from$252
12:20 pm — 0:24 am +1 day	12:20 pm — 5:29 pm WS1572 WestJet Calgary — Houston 4h 18m stop 9:47 pm — 0:24 am NK962 Spirit Airlines Houston — Chicago	11h 4m including layover	Find flight from$252
3:15 pm — 10:02 pm +1 day	3:15 pm — 6:27 pm WS1492 WestJet Calgary — Phoenix 23h 17m stop 5:44 pm — 10:02 pm F91736 Frontier Airlines Phoenix — Chicago	29h 47m including layover	Find flight from$177
4:45 pm — 5:30 am +1 day	3:45 pm — 5:40 pm WS1624 WestJet Calgary — Las Vegas 5h 17m stop 11:17 pm — 4:45 am NK182 Spirit Airlines Las Vegas — Chicago	11h 45m including layover	Find flight from$204
5:15 pm — 9:52 am +1 day	5:15 pm — 0:22 am WS1418 WestJet Calgary — Orlando 7h 8m stop 7:30 am — 9:52 am F93043 Frontier Airlines Orlando — Chicago	15h 37m including layover	Find flight from$250
8:00 am — 7:45 pm	8:00 am — 11:13 am WS1394 WestJet Calgary — Phoenix 4h 4m stop 3:17 pm — 7:45 pm F91830 Frontier Airlines Phoenix — Chicago	10h 45m including layover	Find flight from$179
0:30 am — 0:20 am +1 day	0:30 am — 6:52 am WS1992 WestJet Calgary — Atlanta 10h 28m stop 5:20 pm — 7:25 pm F92298 Frontier Airlines Atlanta — Philadelphia 3h 32m stop 10:57 pm — 0:20 am F94367 Frontier Airlines Philadelphia — Chicago	22h 50m including layover	Find flight from$195
10:30 am — 0:17 am +1 day	10:30 am — 12:29 pm WS1424 WestJet Calgary — Las Vegas 3h 9m stop 3:38 pm — 6:40 pm F92430 Frontier Airlines Las Vegas — Denver 2h 15m stop 8:55 pm — 0:17 am F92210 Frontier Airlines Denver — Chicago	12h 47m including layover	Find flight from$246
11:20 pm — 11:24 pm +2 days	11:20 pm — 0:01 am WS135 WestJet Calgary — Vancouver 22h 59m stop 11:00 pm — 6:53 am WS1598 WestJet Vancouver — Atlanta 15h 30m stop 10:23 pm — 11:24 pm F92779 Frontier Airlines Atlanta — Chicago	47h 4m including layover	Find flight from$195
11:20 pm — 11:47 pm +2 days	11:20 pm — 0:01 am WS135 WestJet Calgary — Vancouver 22h 59m stop 11:00 pm — 6:53 am WS1598 WestJet Vancouver — Atlanta 15h 36m stop 10:29 pm — 11:47 pm F91441 Frontier Airlines Atlanta — Chicago	47h 27m including layover	Find flight from$208
1:10 pm — 11:48 am +1 day	1:10 pm — 4:22 pm WS1410 WestJet Calgary — Phoenix 3h 3m stop 7:25 pm — 7:40 pm F94113 Frontier Airlines Phoenix — Las Vegas 10h 31m stop 6:11 am — 11:48 am F92330 Frontier Airlines Las Vegas — Chicago	21h 38m including layover	Find flight from$184
1:20 pm — 9:47 am +1 day	1:20 pm — 2:21 pm WS1552 WestJet Calgary — Seattle 6h 7m stop 8:28 pm — 0:14 am F91176 Frontier Airlines Seattle — Denver 5h 56m stop 6:10 am — 9:47 am F91484 Frontier Airlines Denver — Chicago	19h 27m including layover	Find flight from$214
2:00 pm — 12:05 pm +1 day	2:00 pm — 2:44 pm WS117 WestJet Calgary — Vancouver 1h 51m stop 4:35 pm — 7:29 pm WS1698 WestJet Vancouver — Los Angeles 10h 31m stop 6:00 am — 12:05 pm NK466 Spirit Airlines Los Angeles — Chicago	21h 5m including layover	Find flight from$230
2:30 pm — 5:33 am +1 day	2:30 pm — 4:52 pm WS1514 WestJet Calgary — Los Angeles 4h 29m stop 9:30 pm — 10:49 pm F93292 Frontier Airlines Los Angeles — Las Vegas 1h 19m stop 6:11 am — 11:48 am F92330 Frontier Airlines Las Vegas — Chicago	14h 3m including layover	Find flight from$206
3:15 pm — 2:46 pm +1 day	3:15 pm — 6:27 pm WS1492 WestJet Calgary — Phoenix 11h 38m stop 6:05 am — 9:29 am F92532 Frontier Airlines Phoenix — Dallas 2h 48m stop 12:17 pm — 2:46 pm F93242 Frontier Airlines Dallas — Chicago	22h 31m including layover	Find flight from$202
4:30 pm — 6:32 pm +1 day	4:30 pm — 7:35 pm WS530 WestJet Calgary — Winnipeg 11h 20m stop 6:55 am — 8:31 am WS6326 WestJet Winnipeg — Minneapolis 8h 24m stop 4:55 pm — 6:32 pm WS8311 WestJet Minneapolis — Chicago	25h 2m including layover	Find flight from$392
5:15 pm — 2:01 pm +1 day	5:15 pm — 0:22 am WS1418 WestJet Calgary — Orlando 8h 55m 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 46m including layover	Find flight from$231
6:50 am — 8:14 pm	6:50 am — 7:36 am WS101 WestJet Calgary — Vancouver 1h 39m stop 9:15 am — 1:22 pm WS1770 WestJet Vancouver — Phoenix 2h 33m stop 3:55 pm — 8:14 pm F91736 Frontier Airlines Phoenix — Chicago	12h 24m including layover	Find flight from$191
6:50 am — 10:22 pm	6:50 am — 7:36 am WS101 WestJet Calgary — Vancouver 1h 39m stop 9:15 am — 1:22 pm WS1770 WestJet Vancouver — Phoenix 4h 43m stop 6:05 pm — 10:22 pm F91738 Frontier Airlines Phoenix — Chicago	14h 32m including layover	Find flight from$191
7:10 pm — 0:17 am +2 days	7:10 pm — 10:22 pm WS1536 WestJet Calgary — Phoenix 19h 1m stop 5:23 pm — 7:21 pm F92106 Frontier Airlines Phoenix — Denver 1h 34m stop 8:55 pm — 0:17 am F92210 Frontier Airlines Denver — Chicago	28h 7m including layover	Find flight from$178
7:10 pm — 5:25 pm +1 day	7:10 pm — 10:22 pm WS1536 WestJet Calgary — Phoenix 11h stop 9:22 am — 9:39 am F93983 Frontier Airlines Phoenix — Las Vegas 1h 58m stop 11:37 am — 5:25 pm F92146 Frontier Airlines Las Vegas — Chicago	21h 15m including layover	Find flight from$178
8:00 pm — 11:24 pm +1 day	8:00 pm — 9:04 pm WS3137 WestJet Calgary — Edmonton 3h 41m stop 0:45 am — 7:06 am WS1940 WestJet Edmonton — Atlanta 15h 17m stop 10:23 pm — 11:24 pm F92779 Frontier Airlines Atlanta — Chicago	26h 24m including layover	Find flight from$170
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$169
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$179

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

*Departure and arrival times are local. Last updated on 04/11/2025

Flight Information

There are 603 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 5h 14m. The time difference between Calgary and Chicago is 1h.

The fastest flight 5h 14m
Average flight time 16h 5m
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 169 $), february (from 172 $), december (from 177 $).

The most expensive and popular months are november (from 178 $), december (from 177 $), february (from 172 $).

The cheapest flight by WestJet that our users were able to find is $169. 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:

Boeing 737-100/200

from $235

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Boeing 737-800

from $252

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Boeing 737-700

from $309

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De Havilland Canada DHC-8-400 Dash 8Q

from $309

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Boeing 737 MAX 8

from $334

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Airbus A319

from $547

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Airbus A320

from $617

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Airbus A318/319/320/321

from $623

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Other Popular Airlines on the Route

Besides WestJet there are other 8 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 2 direct flights every day from Calgary. Airlines and fares are below:

AC - Air Canada

from $989

Find
UA - United Airlines

from $343

Find

See more direct flights

Connecting Flights

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

AA - American Airlines

from $331

Find
F8 - Freedom Airlines

from $183

Find
AC - Air Canada

from $214

Find
AS - Alaska Airlines

from $288

Find
PD - Porter Airlines

from $245

Find
DL - Delta Air Lines Inc.

from $251

Find
UA - United Airlines

from $156

Find
TS - Air Transat

from $417

Find

See more connecting flights

How to book an air ticket yourself?

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