Alaska Airlines Calgary to Chicago Flights

Return flight: Chicago – Calgary
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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 $244 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 february: one-way - $244, two-way – $418.
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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 $244. There’re no direct flights. The fastest connecting flight – 9h 54m.
Price Departure Arrival Flight Time Airline Flight
from $244
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 $308
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 01/22/2025
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 Arrival 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$315
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$244
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$253
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$284
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$308
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$308
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$308
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$330
*Departure and arrival times are local. Last updated on 01/22/2025

Flight Information

There are 9 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 244 $), january (from 266 $).

The cheapest flight by Alaska Airlines that our users were able to find is $244. 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.

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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 4 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:

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Connecting Flights

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

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How to book an air ticket yourself?

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.

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