Cheap Flights from Calgary, AB to Chicago, IL from $153

One way Round trip

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On Cheapflightsplus.com you will find 1 direct and 57 connecting flights from Calgary to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $153, book and save on cheap plane tickets and last minute offers. Also check out YYC-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Calgary to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $153 (one-way), $262 (round-trip).

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Best Flights from Calgary to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Calgary to Chicago with the lowest price of $153. The fastest direct flight takes 3h 27m and the fastest connecting – 7h 36m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $310 Find flight	12:41 Calgary Calgary Int.	17:08 Chicago O'Hare International	3h 27m	United Airlines	UA1655
from $161 Find flight	19:10 Calgary Calgary Int.	10:42+1 день Chicago Midway	14h 32m layover 7h 56m - Phoenix	WestJet	WS1536 F91736
from $173 Find flight	09:55 Calgary Calgary Int.	20:49 Chicago Midway	9h 54m layover 3h 35m - Atlanta	WestJet	WS1590 F92779
from $213 Find flight	00:30 Calgary Calgary Int.	10:55 Chicago Midway	9h 25m layover 3h 6m - Atlanta	WestJet	WS1992 F92143
from $224 Find flight	08:00 Calgary Calgary Int.	01:52+1 день Chicago O'Hare International	16h 52m layover 9h 56m - Phoenix	WestJet	WS1394 F91828
from $250 Find flight	15:15 Calgary Calgary Int.	01:52+1 день Chicago O'Hare International	9h 37m layover 2h 42m - Phoenix	WestJet	WS1492 F91828
from $153 Find flight	21:45 Calgary Calgary Int.	20:49+1 день Chicago Midway	22h 4m layover 1h 58m - Edmonton 12h 48m - Atlanta	WestJet	WS289 WS1940 F92779
from $186 Find flight	18:55 Calgary Calgary Int.	10:39+1 день Chicago O'Hare International	14h 44m layover 3h 58m - Las Vegas 2h 16m - Dallas	WestJet	WS1400 F91650 F93242
from $226 Find flight	09:20 Calgary Calgary Int.	04:47+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	09:20 Calgary Calgary Int.	06:33+1 день Chicago Midway	20h 13m layover 8h 55m - San Diego 2h 44m - Las Vegas	WestJet	WS1564 F91470 F92330
from $227 Find flight	23:20 Calgary Calgary Int.	01:59+2 дня Chicago O'Hare International	25h 39m layover 9h 14m - Vancouver 7h 54m - Phoenix	WestJet	WS135 WS1770 F91828
from $229 Find flight	08:00 Calgary Calgary Int.	01:03+1 день Chicago O'Hare International	16h 3m layover 5h 7m - Phoenix 3h 6m - Denver	WestJet	WS1394 F92106 F93172
from $229 Find flight	08:00 Calgary Calgary Int.	09:13+1 день Chicago Midway	24h 13m layover 12h 42m - Phoenix 0h 55m - Orlando	WestJet	WS1394 F91086 F91457
from $232 Find flight	11:00 Calgary Calgary Int.	10:39+1 день Chicago O'Hare International	22h 39m layover 11h 16m - San Francisco 2h 2m - Dallas	WestJet	WS1508 F94000 F93242
from $232 Find flight	23:20 Calgary Calgary Int.	06:33+2 дня Chicago Midway	30h 13m layover 17h 29m - Vancouver 4h 43m - Las Vegas	WestJet	WS135 WS1790 F92330
from $237 Find flight	23:40 Calgary Calgary Int.	23:59+1 день Chicago O'Hare International	23h 19m layover 9h 7m - Kelowna 8h 3m - Seattle	WestJet	WS279 WS3750 AS538

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on February 22, 2025

Flight Schedule Calgary (Alberta) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Calgary to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
12:41 — 17:08	12:41 — 17:08 UA1655 United Airlines Calgary — Chicago	3h 27m	Find flight from$310
00:30 — 10:55	00:30 — 06:52 WS1992 WestJet Calgary — Atlanta 3h 6m stop 16:12 — 17:12 F92143 Frontier Airlines Atlanta — Chicago	9h 25m including layover	Find flight from$213
00:30 — 16:31	00:30 — 06:54 WS1992 WestJet Calgary — Atlanta 8h 29m stop 15:23 — 16:31 F91595 Frontier Airlines Atlanta — Chicago	15h 1m including layover	Find flight from$228
07:45 — 21:55	07:00 — 10:49 WS6392 WestJet Calgary — Minneapolis 8h 39m stop 20:45 — 22:14 WS8238 WestJet Minneapolis — Chicago	13h 10m including layover	Find flight from$293
07:45 — 16:51	07:45 — 11:41 WS6392 WestJet Calgary — Minneapolis 3h 34m stop 15:15 — 16:51 WS7774 WestJet Minneapolis — Chicago	8h 6m including layover	Find flight from$296
08:00 — 01:52 +1 day	08:00 — 11:15 WS1394 WestJet Calgary — Phoenix 9h 56m stop 21:11 — 01:52 F91828 Frontier Airlines Phoenix — Chicago	16h 52m including layover	Find flight from$224
09:55 — 20:49	09:55 — 16:17 WS1590 WestJet Calgary — Atlanta 3h 35m stop 22:28 — 23:29 F92779 Frontier Airlines Atlanta — Chicago	9h 54m including layover	Find flight from$173
15:15 — 01:52 +1 day	15:15 — 18:29 WS1492 WestJet Calgary — Phoenix 2h 42m stop 21:11 — 01:52 F91828 Frontier Airlines Phoenix — Chicago	9h 37m including layover	Find flight from$250
18:55 — 04:47 +1 day	18:55 — 20:51 WS1400 WestJet Calgary — Las Vegas 2h 5m stop 13:39 — 19:30 F92146 Frontier Airlines Las Vegas — Chicago	8h 52m including layover	Find flight from$224
19:10 — 10:42 +1 day	19:10 — 22:22 WS1536 WestJet Calgary — Phoenix 7h 56m stop 16:28 — 20:47 F91736 Frontier Airlines Phoenix — Chicago	14h 32m including layover	Find flight from$161
06:00 — 16:51	06:00 — 09:08 WS140 WestJet Calgary — Winnipeg 3h 32m stop 12:40 — 14:10 WS6770 WestJet Winnipeg — Minneapolis 1h 5m stop 15:15 — 16:51 WS7774 WestJet Minneapolis — Chicago	9h 51m including layover	Find flight from$355
06:00 — 18:11	06:00 — 09:08 WS140 WestJet Calgary — Winnipeg 3h 32m stop 12:40 — 14:10 WS6770 WestJet Winnipeg — Minneapolis 2h 20m stop 16:30 — 18:11 WS7756 WestJet Minneapolis — Chicago	11h 11m including layover	Find flight from$440
08:00 — 01:03 +1 day	08:00 — 11:15 WS1394 WestJet Calgary — Phoenix 5h 7m stop 16:22 — 18:21 F92106 Frontier Airlines Phoenix — Denver 3h 6m stop 21:27 — 01:03 F93172 Frontier Airlines Denver — Chicago	16h 3m including layover	Find flight from$229
09:20 — 04:47 +1 day	09:20 — 11:46 WS1564 WestJet Calgary — San Diego 8h 55m stop 20:41 — 22:15 F91470 Frontier Airlines San Diego — Las Vegas 44m stop 22:59 — 04:47 F92146 Frontier Airlines Las Vegas — Chicago	18h 27m including layover	Find flight from$226
11:00 — 10:39 +1 day	11:00 — 13:06 WS1508 WestJet Calgary — San Francisco 11h 16m stop 00:22 — 05:58 F94000 Frontier Airlines San Francisco — Dallas 2h 2m stop 08:00 — 10:39 F93242 Frontier Airlines Dallas — Chicago	22h 39m including layover	Find flight from$232
11:00 — 21:55	11:00 — 11:43 WS111 WestJet Calgary — Vancouver 1h 32m stop 13:15 — 18:48 WS6334 WestJet Vancouver — Minneapolis 1h 32m stop 20:20 — 21:55 WS8238 WestJet Minneapolis — Chicago	9h 55m including layover	Find flight from$355
12:30 — 21:55	12:30 — 15:35 WS738 WestJet Calgary — Winnipeg 2h 3m stop 17:45 — 19:20 WS6853 WestJet Winnipeg — Minneapolis 1h 12m stop 20:45 — 22:14 WS8238 WestJet Minneapolis — Chicago	8h 25m including layover	Find flight from$306
14:30 — 09:08 +1 day	14:30 — 16:54 WS1514 WestJet Calgary — Los Angeles 5h 37m stop 22:31 — 06:04 F93216 Frontier Airlines Los Angeles — Atlanta 1h 56m stop 08:00 — 09:08 F91441 Frontier Airlines Atlanta — Chicago	17h 38m including layover	Find flight from$241
14:35 — 04:47 +1 day	14:35 — 15:36 WS3135 WestJet Calgary — Edmonton 1h 39m stop 17:15 — 19:25 WS1450 WestJet Edmonton — Las Vegas 3h 34m stop 22:59 — 04:47 F92146 Frontier Airlines Las Vegas — Chicago	13h 12m including layover	Find flight from$262
15:15 — 06:33 +1 day	15:15 — 18:27 WS1492 WestJet Calgary — Phoenix 2h 36m stop 21:59 — 22:13 F94113 Frontier Airlines Phoenix — Las Vegas 3h 35m stop 06:11 — 11:48 F92330 Frontier Airlines Las Vegas — Chicago	14h 18m including layover	Find flight from$190
18:55 — 10:39 +1 day	18:55 — 20:51 WS1400 WestJet Calgary — Las Vegas 3h 58m stop 00:59 — 05:48 F91650 Frontier Airlines Las Vegas — Dallas 2h 16m stop 09:05 — 11:26 F93242 Frontier Airlines Dallas — Chicago	14h 44m including layover	Find flight from$186
19:10 — 15:53 +1 day	19:10 — 22:24 WS1536 WestJet Calgary — Phoenix 10h 6m stop 08:30 — 11:57 F92532 Frontier Airlines Phoenix — Dallas 1h 34m stop 13:31 — 15:53 F91888 Frontier Airlines Dallas — Chicago	19h 43m including layover	Find flight from$207
21:45 — 20:49 +1 day	21:45 — 22:49 WS289 WestJet Calgary — Edmonton 1h 58m stop 00:45 — 07:06 WS1940 WestJet Edmonton — Atlanta 12h 48m stop 22:28 — 23:29 F92779 Frontier Airlines Atlanta — Chicago	22h 4m including layover	Find flight from$153
21:45 — 10:55 +1 day	21:45 — 22:49 WS289 WestJet Calgary — Edmonton 1h 58m stop 00:45 — 07:06 WS1940 WestJet Edmonton — Atlanta 2h 54m stop 16:12 — 17:12 F92143 Frontier Airlines Atlanta — Chicago	12h 10m including layover	Find flight from$162
23:20 — 01:59 +2 days	23:20 — 00:01 WS135 WestJet Calgary — Vancouver 9h 14m stop 09:15 — 13:24 WS1770 WestJet Vancouver — Phoenix 7h 54m stop 21:18 — 01:59 F91828 Frontier Airlines Phoenix — Chicago	25h 39m including layover	Find flight from$227
23:20 — 06:33 +2 days	23:20 — 00:04 WS135 WestJet Calgary — Vancouver 17h 29m stop 17:30 — 20:15 WS1790 WestJet Vancouver — Las Vegas 4h 43m stop 16:09 — 21:54 F92330 Frontier Airlines Las Vegas — Chicago	30h 13m including layover	Find flight from$232

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

*Departure and arrival times - local. Updated on February 22, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Calgary to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Calgary and Chicago is 2249 miles. Time difference between the cities is 1h. Airplanes depart 00:20 to 23:40 from 1 Calgary airport and arrive 00:20 to 23:40 to 7 Chicago airports. Average flight time is 3h 27m.

The fastest flight 3h 27m
Average flight time 3h 27m
The earliest flight 00:20
The latest flight 23:40
Distance 1398 ml

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

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

What is the lowest airfare Calgary to Chicago?

The cheapest plane ticket found by our users is $153. This airfare is for economy class on one-way WS289 flight by WestJet for February 21, 2025 which leaves Calgary Int. in Calgary at 21:45 am and arrives at Chicago Midway at 20:49.

Economy class

$153

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Business class

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First class

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Popular Airlines on the Route

The flight Calgary — Chicago is served by 4 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by Alaska Airlines - 1 departures per week at the price of from $ 335 . And the most expensive tickets are offered by United Airlines airline - from $ 584.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA1655 by United Airlines takes 3h 27m and the cheapest is WS289 by WestJet for $310.

UA - United Airlines

from $310

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Connecting Flights

There are 57 flights with layovers on the route. The fastest connecting flight is UA1953 by United Airlines takes 7h 36m and the cheapest is WS289 by WestJet for $153.

AS - Alaska Airlines

from $335

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WS - WestJet

from $153

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UA - United Airlines

from $314

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F8 - Freedom Airlines

from $266

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Airports

You can fly from Calgary to Chicago from 1 airports (Calgary Int.).

Calgary airports

Calgary Int.-YYC

from $153
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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from Calgary by 4 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top International Destinations from Calgary

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Calgary — Las Vegas

from $58

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Calgary — New York

from $58

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Calgary — Seattle

from $70

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Calgary — Chicago

from $59

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Calgary — Nashville

from $70

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Calgary — Denver

from $61

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Calgary — San Francisco

from $69

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Calgary — Houston

from $56

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Calgary — Palm Springs

from $77

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Calgary — Atlanta

from $74

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How to book a plane 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 flight ticket.
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.