Alaska Airlines Calgary to Chicago Flights

One way Round trip

Adults

Children under 12

Infants under 2 without place

Economy

Business

First

done

Return flight: Chicago – Calgary

Page navigation

Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap Alaska Airlines flights from Calgary to Chicago. Compare airline ticket prices and book air tickets starting from $260 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Alaska Airlines, arrivals and departure details below.

Find Cheap Airfare Calgary (AB) — Chicago (IL) by Alaska Airlines

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 - $260, two-way – $446.

Direct flights

Check to choose departure date Check to choose departure date

Check prices for return flight

Find flights

Cheap Flights from Calgary to Chicago by Alaska Airlines

Look at the list of plane tickets for the most connecting flights by Alaska Airlines, their prices start from $260. There’re no direct flights. The fastest connecting flight – 9h 54m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $260 Find flight	7:00 pm Calgary Calgary Int.	11:59 pm+1 день Chicago O'Hare International	27h 59m layover 22h 4m - Seattle	Alaska Airlines	AS2226 AS538
from $328 Find flight	7:00 pm Calgary Calgary Int.	1:07 pm+1 день Chicago O'Hare International	17h 7m layover 1h 3m - Seattle 9h 7m - Portland	Alaska Airlines	AS2226 AS123 AS324

Show All Flights

*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 12/22/2024

Alaska Airlines 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
6:59 pm — 5:53 am +1 day	6:59 pm — 7:48 pm AS2226 Alaska Airlines Calgary — Seattle 4h 11m stop 11:59 pm — 5:53 am AS461 Alaska Airlines Seattle — Chicago	9h 54m including layover	Find flight from$335
7:00 pm — 11:59 pm +1 day	7:00 pm — 7:56 pm AS2226 Alaska Airlines Calgary — Seattle 22h 4m stop 6:00 pm — 11:59 pm AS538 Alaska Airlines Seattle — Chicago	27h 59m including layover	Find flight from$260
7:00 pm — 2:40 pm +1 day	7:00 pm — 7:56 pm AS2226 Alaska Airlines Calgary — Seattle 12h 29m stop 8:25 am — 2:40 pm AS408 Alaska Airlines Seattle — Chicago	18h 40m including layover	Find flight from$270
7:00 pm — 5:59 pm +1 day	7:00 pm — 7:56 pm AS2226 Alaska Airlines Calgary — Seattle 15h 49m stop 11:45 am — 5:59 pm AS352 Alaska Airlines Seattle — Chicago	21h 59m including layover	Find flight from$303
7:00 pm — 1:07 pm +1 day	7:00 pm — 7:56 pm AS2226 Alaska Airlines Calgary — Seattle 1h 3m stop 8:59 pm — 9:53 pm AS123 Alaska Airlines Seattle — Portland 9h 7m stop 7:00 am — 1:07 pm AS324 Alaska Airlines Portland — Chicago	17h 7m including layover	Find flight from$328
7:00 pm — 1:07 pm +1 day	7:00 pm — 7:56 pm AS2226 Alaska Airlines Calgary — Seattle 2h 55m stop 10:51 pm — 11:43 pm AS957 Alaska Airlines Seattle — Portland 7h 17m stop 7:00 am — 1:07 pm AS324 Alaska Airlines Portland — Chicago	17h 7m including layover	Find flight from$328
7:00 pm — 1:07 pm +1 day	7:00 pm — 7:56 pm AS2226 Alaska Airlines Calgary — Seattle 2h 3m stop 9:59 pm — 10:54 pm AS955 Alaska Airlines Seattle — Portland 8h 6m stop 7:00 am — 1:07 pm AS324 Alaska Airlines Portland — Chicago	17h 7m including layover	Find flight from$328
7:00 pm — 10:02 am +1 day	7:00 pm — 7:56 pm AS2226 Alaska Airlines Calgary — Seattle 1h 19m stop 9:15 pm — 5:40 am AS394 Alaska Airlines Seattle — Orlando 2h 20m stop 8:26 am — 10:28 am F91457 Frontier Airlines Orlando — Chicago	14h 2m including layover	Find flight from$351
7:00 pm — 11:44 am +1 day	7:00 pm — 7:56 pm AS2226 Alaska Airlines Calgary — Seattle 1h 33m stop 9:29 pm — 11:59 pm AS704 Alaska Airlines Seattle — Las Vegas 6h 12m stop 6:11 am — 11:44 am F92330 Frontier Airlines Las Vegas — Chicago	15h 44m including layover	Find flight from$360
7:00 pm — 11:40 am +1 day	7:00 pm — 7:56 pm AS2226 Alaska Airlines Calgary — Seattle 1h 19m stop 9:15 pm — 5:39 am AS360 Alaska Airlines Seattle — Tampa 4h 5m stop 9:44 am — 11:40 am F91185 Frontier Airlines Tampa — Chicago	15h 40m including layover	Find flight from$409

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

*Departure and arrival times are local. Last updated on 12/22/2024

Flight Information

There are 11 flights by Alaska Airlines 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 6:59 pm to 7:00 pm. Nonstop flight is 9h 54m. The time difference between Calgary and Chicago is 1h.

The fastest flight 9h 54m
Average flight time 17h 7m
The earliest flight 6:59 pm
The latest flight 7:00 pm
Distance 1398 ml

The cheapest months for traveling to Chicago are february (from 260 $), january (from 284 $).

The cheapest flight by Alaska Airlines that our users were able to find is $260. This airfare is economy class on one-way AS2226 flight for February 1, 2025 leaving Calgary Int. in Calgary at 7:00 pm, it includes all taxes and additional fees.

Find same flight?

Alaska Airlines Airplanes on the Route

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

Other Popular Airlines on the Route

Besides Alaska Airlines there are other 5 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 $315

Find

See more direct flights

Connecting Flights

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

AC - Air Canada

from $314

Find
UA - United Airlines

from $141

Find
WS - WestJet

from $153

Find
F8 - Freedom Airlines

from $169

Find
PD - Porter Airlines

from $311

Find

See more connecting flights

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.