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Cheap Flights from Calgary to Chicago, IL, United States - YYC to CHI

Popular flights from Calgary to Chicago

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
May 30, 2016 Jun 2, 2016 CAD319
May 31, 2016 Jun 3, 2016 CAD319
Jun 1, 2016 Jun 2, 2016 CAD319
Jun 1, 2016 Jun 3, 2016 CAD319
Alaska Airlines
Departure Date Return Date Lowest Price
May 31, 2016 Jun 3, 2016 CAD347
American Airlines
Departure Date Return Date Lowest Price
May 7, 2016 May 10, 2016 CAD356
Frontier Airlines
Departure Date Return Date Lowest Price
Jun 2, 2016 Jun 5, 2016 CAD875
Spirit Airlines
Departure Date Return Date Lowest Price
Jun 2, 2016 Jun 5, 2016 CAD917
United Airlines
Departure Date Return Date Lowest Price
May 28, 2016 Jun 1, 2016 CAD457
May 31, 2016 Jun 3, 2016 CAD457
Jun 1, 2016 Jun 3, 2016 CAD457
Jun 1, 2016 Jun 2, 2016 CAD457
WestJet
Departure Date Return Date Lowest Price
May 17, 2016 May 19, 2016 CAD323

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 CAD324.

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 CAD562 CAD356
7-14 days CAD323 CAD358
14-21 days CAD492 CAD375
21-30 days CAD319 CAD324
30-60 days CAD457 CAD328
60-90 days CAD457 CAD415
90+ days CAD319 CAD324

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
CAD319 CAD319 CAD319 CAD329 CAD333 CAD324 CAD333

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
May Calgary Chicago Air Canada 5/30/16 6/2/16 0 CAD319
June Calgary Chicago Air Canada 6/1/16 6/2/16 0 CAD319
July Calgary Chicago Air Canada 7/7/16 7/12/16 2 CAD341
August Calgary Chicago WestJet 8/17/16 8/23/16 1 CAD418
September Calgary Chicago Air Canada 9/16/16 9/24/16 1 CAD328
October Calgary Chicago Air Canada 10/26/16 10/31/16 0 CAD319
November Calgary Chicago Air Canada 11/3/16 11/6/16 1 CAD324
December Calgary Chicago Air Canada 12/9/16 12/12/16 1 CAD338

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Calgary to Chicago

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Calgary to Chicago.

Next 30 Days

SunMonTueWedThuFriSat
1 2 3 4 5 6 7
CAD573
8 9 10 11 12 13 14
CAD573
15 16 17 18 19 20 21
CAD565
22 23 24 25 26 27 28
CAD565 CAD809
29 30 31 1 2 3 4
CAD809 CAD531
5 6 7 8 9 10 11
CAD531

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 CAD536.

The average price for non-stop flights from Calgary to Chicago is CAD425.

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 4 3 3 3 3 3 2 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 CAD218.

The average price for round trip flights from Calgary to Chicago is CAD533.

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 26 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 73% 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)

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 MSP 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, Air Transat, Sunwing, WestJet CAD453
Calgary to Windsor Air Canada, Air Transat, WestJet CAD448

Cheap International Flights from Calgary - YYC

FlightsAirlineLowest Price
Calgary to New York Central Mountain, American, Air Canada, Alaska, JetBlue, Frontier, United, Virgin America, WestJet CAD373
Calgary to Milwaukee American, Air Canada, Alaska, Frontier, United, WestJet CAD492
Calgary to Detroit American, Air Canada, Alaska, Frontier, Spirit, United, WestJet CAD420
Calgary to Dallas - Ft Worth American, Air Canada, Alaska, Spirit, United, WestJet CAD314
Calgary to Indianapolis American, Air Canada, Alaska, Allegiant, United, WestJet CAD445
Calgary to Minneapolis - St Paul Central Mountain, American, Air Canada, Alaska, Sun Country, United, WestJet CAD508
Calgary to South Bend Air Canada, Alaska, United, WestJet Check Dates
Calgary to Madison American, Air Canada, Alaska, United, WestJet CAD492
Calgary to Atlanta American, Air Canada, Alaska, Frontier, United, WestJet CAD357
Calgary to Grand Rapids American, Air Canada, Alaska, United, WestJet CAD601
Calgary to St Louis American, Air Canada, Alaska, Frontier, United, WestJet CAD351
Calgary to London Aegean, Air Berlin, Air Canada, Air France, Finnair, Alitalia, British Airways, Condor, Pullmantur Air, Aer Lingus, Iberia, Adria, KLM, Lufthansa, LOT, Thomas Cook, Czech, Austrian, SATA, SAS, Brussels, Tap Portugal, Air Transat, Virgin Atlantic, WestJet CAD535
Calgary to Denver Central Mountain, American, Air Canada, Alaska, Frontier, United, WestJet CAD425
Calgary to Los Angeles American, Air Canada, Alaska, JetBlue, United, WestJet CAD273

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Kalispell to Chicago American, Alaska, United CAD652
Edmonton to Toronto Canadian Nth, First Air, Central Mountain, Air Canada, Porter, Sunwing, WestJet CAD451
Kalispell to Milwaukee American, Alaska, United CAD646

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Edmonton to Chicago Central Mountain, American, Air Canada, Alaska, Frontier, Spirit, United, WestJet CAD505
Lethbridge to Chicago Air Canada, United Check Dates
Edmonton to New York American, Air Canada, Alaska, JetBlue, Frontier, Spirit, United, Virgin America, WestJet CAD461
Edmonton to Milwaukee American, Air Canada, Alaska, Frontier, United, WestJet CAD520
Edmonton to Detroit American, Air Canada, Alaska, Spirit, United, WestJet CAD395
Edmonton to South Bend Air Canada, Alaska, United, WestJet Check Dates
Edmonton to Minneapolis - St Paul Central Mountain, American, Air Canada, Alaska, Sun Country, United, WestJet CAD570
Edmonton to Madison American, Air Canada, Alaska, United, WestJet CAD562
Edmonton to Indianapolis American, Air Canada, Alaska, United, WestJet CAD423
Edmonton to Grand Rapids American, Air Canada, Alaska, United, WestJet CAD537
Edmonton to Atlanta American, Air Canada, Alaska, Frontier, United, WestJet CAD413
Cheap Flights from Calgary to Chicago, IL, United States, from CAD255 Round trip from YYC to CHI