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Cheap Flights from Calgary to Chicago, IL, United States - YYC to CHI Last modified: 26-May-2016 7:57 AM

Popular flights from Calgary to Chicago Last modified: 26-May-2016 7:57 AM

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

Air Canada
Departure Date Return Date Lowest Price
4-Jun-2016 18-Jun-2016 $329
21-Jun-2016 25-Jun-2016 $329
Alaska Airlines
Departure Date Return Date Lowest Price
7-Jun-2016 14-Jun-2016 $514
17-Jun-2016 22-Jun-2016 $514
American Airlines
Departure Date Return Date Lowest Price
16-Jun-2016 21-Jun-2016 $417
United Airlines
Departure Date Return Date Lowest Price
16-Jun-2016 21-Jun-2016 $455
WestJet
Departure Date Return Date Lowest Price
4-Jun-2016 11-Jun-2016 $390

How Much Does it Cost to Fly from Calgary to Chicago (YYC to CHI)?

We have collected flight cost data from across the web for travel from Calgary to Chicago, and have found the average flight price for this trip to be $425.

When Can I Buy the Cheapest Flight from Calgary to Chicago (YYC to CHI)?

Airlines can adjust prices for plane tickets from Calgary to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from Calgary to Chicago

The chart below shows up-to-date information regarding how far in advance a flight from Calgary to Chicago should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $534 $583
7-14 days $390 $329
14-21 days $459 $417
21-30 days $424 $329
30-60 days $445 $455
60-90 days $528 $543
90+ days $477 $514

Cheapest Day To Fly from Calgary to Chicago

The chart below shows up-to-date information regarding the cheapest days to fly from Calgary to Chicago.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$543 $329 $456 $417 $424 $329 $475

Lowest Fares Chart By Month from Calgary to Chicago

The chart below shows the lowest fare by month when flying from Calgary to Chicago.

Month Origin Destination Carrier Depart Date Return Date Stops Price
June Calgary Chicago Air Canada 04/06/16 18/06/16 1 $329
July Calgary Chicago WestJet 05/07/16 08/07/16 0 $445
August Calgary Chicago WestJet 26/08/16 27/08/16 0 $526
September Calgary Chicago WestJet 03/09/16 06/09/16 0 $477
October Calgary Chicago WestJet 08/10/16 12/10/16 0 $477
November Calgary Chicago Alaska 15/11/16 23/11/16 1 $572
December Calgary Chicago Alaska 10/12/16 13/12/16 1 $587
March Calgary Chicago United 08/03/17 12/03/17 0 $587

Non-Stop vs Connecting Flights from Calgary to Chicago (YYC to CHI)

Your Calgary to Chicago flight can be significantly cheaper by choosing a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Calgary to Chicago is $434.

The average price for non-stop flights from Calgary to Chicago is $530.

The chart below shows up to date information regarding non-stop flights from Calgary to Chicago.

Nonstop Flight Details from Calgary to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 3 3 3 3 3 3 3 08:10 15:15
WestJet 1 1 1 1 1 1 1 13:35 13:35

Round Trip vs One Way Flights from Calgary to Chicago (YYC to CHI)

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Calgary to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Calgary to Chicago is $265.

The average price for round trip flights from Calgary to Chicago is $428.

Calgary to Chicago Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is a direct flight from Calgary to Chicago?
Answer: The average Calgary to Chicago flight time is 3 hours and 31 minutes.
Question: How many kilometers are there between Calgary and Chicago?
Answer: The distance from Calgary to Chicago is 2222 kilometers.
Question: How common are direct flights from Calgary to Chicago?
Answer: There are 28 direct flights from Calgary to Chicago.
Question: What is the most popular airline for non-stop flights from Calgary to Chicago?
Answer: United Airlines provides 75% of the non-stop flights between Calgary and Chicago.
Question: What are the most popular connecting cities when flying from Calgary to Chicago?
Answer: Minneapolis - St Paul, MN

Airlines Flying from Calgary to Chicago (YYC to CHI) Number of flights searched: 149Last modified: 26-May-2016 7:57 AM

Below are the different airlines that fly from Calgary to Chicago with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Calgary to Chicago.

Calgary to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American DFW X X X X X X X
Air Canada YYZ X X X X X X X
Alaska SEA X X X X X X X
Alaska SEA / PDX X X X X X X X
Delta SLC X X X X X X X
United - X X X X X X X
United DEN X X X X X X X
WestJet - X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Calgary and Chicago, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Calgary - YYC

FlightsAirlineLowest Price
Calgary to Toronto Central Mountain, Air Canada, Porter, Air Transat, Sunwing, WestJet $467
Calgary to Windsor Central Mountain, Air Canada, WestJet $448

Cheap International Flights from Calgary - YYC

FlightsAirlineLowest Price
Calgary to New York Central Mountain, American, Air Canada, Alaska, JetBlue, United, Virgin America, WestJet $391
Calgary to Milwaukee American, Air Canada, Alaska, Frontier, United, WestJet $431
Calgary to Detroit American, Air Canada, Alaska, Spirit, United, WestJet $421
Calgary to Dallas - Ft Worth American, Air Canada, Alaska, United, WestJet $362
Calgary to Indianapolis American, Air Canada, Alaska, United, WestJet $460
Calgary to Minneapolis - St Paul Central Mountain, American, Air Canada, Alaska, Spirit, Sun Country, United, WestJet $510
Calgary to South Bend Air Canada, Alaska, United, WestJet Check Dates
Calgary to Madison American, Air Canada, Alaska, United, WestJet $576
Calgary to Atlanta American, Air Canada, Alaska, Frontier, United, WestJet $337
Calgary to Grand Rapids American, Air Canada, Alaska, Allegiant, United, WestJet $576
Calgary to St Louis American, Air Canada, Alaska, Frontier, United, WestJet $392
Calgary to London Aegean, Air Berlin, Air Canada, Air France, Finnair, Alitalia, British Airways, Condor, Aer Lingus, Iberia, Meridiana, Adria, KLM, Lufthansa, LOT, Thomas Cook, Czech, Austrian, SATA, SAS, Brussels, Jetairfly, Tap Portugal, Air Transat, Virgin Atlantic, WestJet $695
Calgary to Denver Central Mountain, American, Air Canada, Alaska, United, WestJet $463
Calgary to Los Angeles Central Mountain, American, Air Canada, Alaska, United, WestJet $285

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Kalispell to Chicago American, Alaska, United $614
Edmonton to Toronto Canadian Nth, First Air, Central Mountain, Air Canada, Porter, Sunwing, WestJet $456
Kalispell to Milwaukee American, Alaska, United $697

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Edmonton to Chicago American, Air Canada, Alaska, Frontier, Spirit, United, WestJet $484
Lethbridge to Chicago American, Air Canada, United $1,136
Edmonton to New York Central Mountain, American, Air Canada, Alaska, JetBlue, United, Virgin America, WestJet $463
Edmonton to Milwaukee American, Air Canada, Alaska, Frontier, United, WestJet $443
Edmonton to Detroit American, Air Canada, Alaska, Spirit, United, WestJet $401
Edmonton to South Bend Air Canada, Alaska, United, WestJet $1,232
Edmonton to Minneapolis - St Paul American, Air Canada, Alaska, Spirit, Sun Country, United, WestJet $578
Edmonton to Madison American, Air Canada, Alaska, United, WestJet $503
Edmonton to Indianapolis American, Air Canada, Alaska, United, WestJet $485
Edmonton to Grand Rapids American, Air Canada, Alaska, United, WestJet $536
Edmonton to Atlanta American, Air Canada, Alaska, United, WestJet $424
Cheap Flights from Calgary to Chicago, IL, United States, from $251 Round trip from YYC to CHI