Cheap Flights from Calgary, AB to Chicago, IL from $132

One way Round trip

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On Cheapflightsplus.com you will find 1 direct and 133 connecting flights from Calgary to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $132, 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: $132 (one-way), $226 (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 $132. The fastest direct flight takes 3h 27m and the fastest connecting – 7h 36m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $296 Find flight	12:41 Calgary Calgary Int.	17:08 Chicago O'Hare International	3h 27m	United Airlines	UA1655
from $132 Find flight	06:19 Calgary Calgary Int.	19:31 Chicago O'Hare International	12h 12m layover 6h 58m - Denver	United Airlines	UA550 UA1495
from $158 Find flight	16:35 Calgary Calgary Int.	22:22+1 день Chicago Midway	28h 47m layover 22h 10m - Phoenix	Freedom Airlines	F81502 F91738
from $194 Find flight	19:10 Calgary Calgary Int.	10:42+1 день Chicago Midway	14h 32m layover 7h 56m - Phoenix	WestJet	WS1536 F91736
from $195 Find flight	09:35 Calgary Calgary Int.	05:18+1 день Chicago O'Hare International	18h 43m layover 11h 14m - Los Angeles	WestJet	WS1510 NK1679
from $195 Find flight	19:20 Calgary Calgary Int.	00:33+2 дня Chicago O'Hare International	28h 13m layover 20h 47m - Los Angeles	WestJet	WS1512 NK517
from $197 Find flight	14:30 Calgary Calgary Int.	05:18+1 день Chicago O'Hare International	13h 48m layover 6h 21m - Los Angeles	WestJet	WS1514 NK1679
from $144 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 $163 Find flight	19:20 Calgary Calgary Int.	00:17+2 дня Chicago Midway	27h 57m layover 18h 34m - Los Angeles 1h 15m - Denver	WestJet	WS1512 F92342 F92210
from $166 Find flight	23:20 Calgary Calgary Int.	23:24+2 дня Chicago Midway	47h 4m layover 22h 59m - Vancouver 15h 30m - Atlanta	WestJet	WS135 WS1598 F92779
from $169 Find flight	09:35 Calgary Calgary Int.	11:44+1 день Chicago Midway	25h 9m layover 9h 29m - Los Angeles 7h 28m - Las Vegas	WestJet	WS1510 F93292 F92330
from $172 Find flight	08:00 Calgary Calgary Int.	00:17+1 день Chicago Midway	15h 17m layover 6h 10m - Phoenix 1h 34m - Denver	WestJet	WS1394 F92106 F92210
from $179 Find flight	09:55 Calgary Calgary Int.	09:52+1 день Chicago O'Hare International	22h 57m layover 5h 40m - Atlanta 7h 47m - Orlando	WestJet	WS1590 F94026 F92041
from $192 Find flight	23:30 Calgary Calgary Int.	22:22+1 день Chicago Midway	21h 52m layover 6h 28m - Edmonton 7h 34m - Phoenix	WestJet	WS237 WS1532 F91738
from $194 Find flight	15:45 Calgary Calgary Int.	09:16+1 день Chicago O'Hare International	16h 31m layover 6h 11m - Las Vegas 2h 13m - Dallas	WestJet	WS1624 F93886 F93242
from $196 Find flight	09:55 Calgary Calgary Int.	13:43+1 день Chicago O'Hare International	26h 48m layover 15h 58m - Atlanta 1h 54m - Tampa	WestJet	WS1590 F92912 F91415

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on January 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$296
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$214
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$214
06:19 — 19:31	06:19 — 08:57 UA550 United Airlines Calgary — Denver 6h 58m stop 15:55 — 19:31 UA1495 United Airlines Denver — Chicago	12h 12m including layover	Find flight from$132
14:30 — 05:18 +1 day	14:30 — 16:52 WS1514 WestJet Calgary — Los Angeles 6h 21m stop 23:15 — 05:18 NK1679 Spirit Airlines Los Angeles — Chicago	13h 48m including layover	Find flight from$197
16:35 — 22:22 +1 day	16:35 — 19:55 F81502 Freedom Airlines Calgary — Phoenix 22h 10m stop 18:05 — 22:22 F91738 Frontier Airlines Phoenix — Chicago	28h 47m including layover	Find flight from$158
17:15 — 10:02 +1 day	17:15 — 00:22 WS1418 WestJet Calgary — Orlando 7h 37m stop 08:08 — 10:03 F91457 Frontier Airlines Orlando — Chicago	15h 47m including layover	Find flight from$244
18:55 — 06:33 +1 day	18:55 — 20:51 WS1400 WestJet Calgary — Las Vegas 4h 5m stop 06:50 — 12:34 F92330 Frontier Airlines Las Vegas — Chicago	10h 38m including layover	Find flight from$246
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$247
08:00 — 00:17 +1 day	08:00 — 11:13 WS1394 WestJet Calgary — Phoenix 6h 10m stop 17:23 — 19:21 F92106 Frontier Airlines Phoenix — Denver 1h 34m stop 20:55 — 00:17 F92210 Frontier Airlines Denver — Chicago	15h 17m including layover	Find flight from$172
08:00 — 23:59	08:00 — 11:13 WS1394 WestJet Calgary — Phoenix 3h 32m stop 14:45 — 16:59 AS1006 Alaska Airlines Phoenix — Seattle 1h 1m stop 18:00 — 23:59 AS538 Alaska Airlines Seattle — Chicago	14h 59m including layover	Find flight from$208
09:35 — 11:44 +1 day	09:35 — 12:01 WS1510 WestJet Calgary — Los Angeles 9h 29m stop 21:30 — 22:43 F93292 Frontier Airlines Los Angeles — Las Vegas 7h 28m stop 06:11 — 11:44 F92330 Frontier Airlines Las Vegas — Chicago	25h 9m including layover	Find flight from$169
09:55 — 09:52 +1 day	09:55 — 16:19 WS1590 WestJet Calgary — Atlanta 5h 40m stop 21:59 — 23:43 F94026 Frontier Airlines Atlanta — Orlando 7h 47m stop 07:30 — 09:52 F92041 Frontier Airlines Orlando — Chicago	22h 57m including layover	Find flight from$179
10:30 — 00:17 +1 day	10:30 — 12:29 WS1424 WestJet Calgary — Las Vegas 3h 9m stop 15:38 — 18:40 F92430 Frontier Airlines Las Vegas — Denver 2h 15m stop 20:55 — 00:17 F92210 Frontier Airlines Denver — Chicago	12h 47m including layover	Find flight from$209
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$218
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$227
15:45 — 09:16 +1 day	15:45 — 17:44 WS1624 WestJet Calgary — Las Vegas 6h 11m stop 23:55 — 04:42 F93886 Frontier Airlines Las Vegas — Dallas 2h 13m stop 06:55 — 09:16 F93242 Frontier Airlines Dallas — Chicago	16h 31m including layover	Find flight from$194
15:45 — 13:06 +1 day	15:45 — 17:44 WS1624 WestJet Calgary — Las Vegas 6h 11m stop 23:55 — 04:42 F93886 Frontier Airlines Las Vegas — Dallas 6h 2m stop 10:44 — 13:06 F91888 Frontier Airlines Dallas — Chicago	20h 21m including layover	Find flight from$200
16:35 — 13:06 +1 day	16:35 — 19:55 F81502 Freedom Airlines Calgary — Phoenix 10h 10m stop 06:05 — 09:33 F92532 Frontier Airlines Phoenix — Dallas 1h 11m stop 10:44 — 13:06 F91888 Frontier Airlines Dallas — Chicago	19h 31m including layover	Find flight from$180
17:15 — 13:06 +1 day	17:15 — 00:23 WS1418 WestJet Calgary — Orlando 5h 37m stop 06:00 — 08:17 F91481 Frontier Airlines Orlando — Dallas 2h 27m stop 10:44 — 13:06 F91888 Frontier Airlines Dallas — Chicago	18h 51m including layover	Find flight from$233
19:10 — 17:25 +1 day	19:10 — 22:22 WS1536 WestJet Calgary — Phoenix 11h stop 09:22 — 09:39 F93983 Frontier Airlines Phoenix — Las Vegas 1h 58m stop 11:37 — 17:25 F92146 Frontier Airlines Las Vegas — Chicago	21h 15m including layover	Find flight from$151
19:10 — 00:17 +2 days	19:10 — 22:22 WS1536 WestJet Calgary — Phoenix 19h 1m stop 17:23 — 19:21 F92106 Frontier Airlines Phoenix — Denver 1h 34m stop 20:55 — 00:17 F92210 Frontier Airlines Denver — Chicago	28h 7m including layover	Find flight from$151
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$144
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$166
23:20 — 23:24 +2 days	23:20 — 00:01 WS135 WestJet Calgary — Vancouver 22h 59m stop 23:00 — 06:53 WS1598 WestJet Vancouver — Atlanta 15h 30m stop 22:23 — 23:24 F92779 Frontier Airlines Atlanta — Chicago	47h 4m including layover	Find flight from$166
23:20 — 23:47 +2 days	23:20 — 00:01 WS135 WestJet Calgary — Vancouver 22h 59m stop 23:00 — 06:53 WS1598 WestJet Vancouver — Atlanta 15h 36m stop 22:29 — 23:47 F91441 Frontier Airlines Atlanta — Chicago	47h 27m including layover	Find flight from$176

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

*Departure and arrival times - local. Updated on January 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 february (from 132 $), january (from 144 $), december (from 152 $).

The most expensive months are november (from 173 $), december (from 152 $), january (from 144 $).

What is the lowest airfare Calgary to Chicago?

The cheapest plane ticket found by our users is $132. This airfare is for economy class on one-way UA550 flight by United Airlines for February 1, 2025 which leaves Calgary Int. in Calgary at 06:19 am and arrives at Chicago O'Hare International at 19:31.

Economy class

$132

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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 5 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by Air Canada - 2 departures per week at the price of from $ 294 . And the most expensive tickets are offered by WestJet airline - from $ 577.

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 UA550 by United Airlines for $296.

UA - United Airlines

from $296

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Connecting Flights

There are 133 flights with layovers on the route. The fastest connecting flight is UA1953 by United Airlines takes 7h 36m and the cheapest is UA550 by United Airlines for $132.

AS - Alaska Airlines

from $244

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AC - Air Canada

from $294

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UA - United Airlines

from $132

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WS - WestJet

from $144

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F8 - Freedom Airlines

from $158

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See more connecting flights

Airports

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

Calgary airports

Calgary Int.-YYC

from $132
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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 5 airlines that use 3 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737-800

from $215

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Boeing 737 MAX 8

from $283

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Airbus A320

from $328

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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.