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

Popular flights from Calgary to Chicago

If your flight days are flexible and you looking for a good deal, our charts on cheap flights provide some insight regarding affordable flight options for your next big adventure.

Air Canada
Departure Date Return Date Lowest Price
May 16, 2016 May 17, 2016 CAD435
May 26, 2016 May 27, 2016 CAD435
Alaska Airlines
Departure Date Return Date Lowest Price
May 20, 2016 May 24, 2016 CAD432
American Airlines
Departure Date Return Date Lowest Price
May 23, 2016 May 24, 2016 CAD407
United Airlines
Departure Date Return Date Lowest Price
Jun 2, 2016 Jun 7, 2016 CAD412
WestJet
Departure Date Return Date Lowest Price
May 3, 2016 May 10, 2016 CAD346
May 24, 2016 May 31, 2016 CAD346
Jun 7, 2016 Jun 15, 2016 CAD346

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 CAD435.

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 CAD1,620 CAD668
7-14 days CAD490 CAD482
14-21 days CAD487 CAD479
21-30 days CAD487 CAD479
30-60 days CAD487 CAD479
60-90 days CAD346 CAD421
90+ days CAD346 CAD408

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
CAD479 CAD346 CAD490 CAD372 CAD446 CAD479 CAD436

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
February Calgary Chicago American 2/25/16 2/28/16 1 CAD482
March Calgary Chicago American 3/5/16 3/14/16 1 CAD479
April Calgary Chicago American 4/29/16 5/2/16 1 CAD446
May Calgary Chicago WestJet 5/3/16 5/10/16 0 CAD346
June Calgary Chicago WestJet 6/7/16 6/15/16 0 CAD346
July Calgary Chicago WestJet 7/20/16 8/3/16 0 CAD494
August Calgary Chicago WestJet 8/6/16 8/9/16 0 CAD522
September Calgary Chicago Alaska 9/3/16 9/15/16 1 CAD531

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
14 15 16 17 18 19 20
CAD1,620
21 22 23 24 25 26 27
CAD1,620 CAD490
28 29 1 2 3 4 5
CAD490
6 7 8 9 10 11 12
CAD499
13 14 15 16 17 18 19
CAD499 CAD493
20 21 22 23 24 25 26
CAD493

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 CAD490.

The average price for non-stop flights from Calgary to Chicago is CAD435.

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 2 3 3 3 2 3 06:15 15:15

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 CAD259.

The average price for round trip flights from Calgary to Chicago is CAD439.

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 19 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 100% 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

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 CAD435
Calgary to Windsor Central Mountain, Air Canada, WestJet CAD450

Cheap International Flights from Calgary - YYC

FlightsAirlineLowest Price
Calgary to New York Central Mountain, American, Air Canada, Alaska, JetBlue, Spirit, United, Virgin America, WestJet CAD396
Calgary to Milwaukee American, Air Canada, Alaska, Frontier, United, WestJet CAD416
Calgary to Detroit American, Air Canada, Alaska, Spirit, United, WestJet CAD401
Calgary to Dallas - Ft Worth Central Mountain, American, Air Canada, Alaska, Spirit, Sun Country, United, WestJet CAD361
Calgary to Indianapolis American, Air Canada, Alaska, United, WestJet CAD450
Calgary to Minneapolis - St Paul American, Air Canada, Alaska, Spirit, Sun Country, United, WestJet CAD533
Calgary to South Bend Air Canada, Alaska, United, WestJet CAD608
Calgary to Madison American, Air Canada, Alaska, United, WestJet CAD437
Calgary to Atlanta American, Air Canada, Alaska, Frontier, United, WestJet CAD295
Calgary to Grand Rapids American, Air Canada, Alaska, United, WestJet CAD421
Calgary to St Louis American, Air Canada, Alaska, United, WestJet CAD348
Calgary to London Aegean, Air Berlin, Air Canada, Air France, Finnair, Alitalia, British Airways, airBaltic, Condor, Aer Lingus, Iberia, KLM, Lufthansa, LOT, Thomas Cook, Czech, Austrian, SATA, SAS, Brussels, Tap Portugal, Air Transat, Virgin Atlantic, WestJet CAD775
Calgary to Denver Central Mountain, American, Air Canada, Alaska, United, WestJet CAD389
Calgary to Los Angeles Central Mountain, American, Air Canada, Alaska, JetBlue, United, WestJet CAD318

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Kalispell to Chicago Alaska, United CAD588
Edmonton to Toronto Canadian Nth, First Air, Central Mountain, Air Canada, Air Transat, Sunwing, WestJet CAD437
Kalispell to Milwaukee American, Alaska, United CAD1,086

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Edmonton to Chicago Central Mountain, American, Air Canada, Alaska, Frontier, United, WestJet CAD358
Lethbridge to Chicago American, Air Canada, United Check Dates
Edmonton to New York American, Air Canada, Alaska, JetBlue, United, WestJet CAD410
Edmonton to Milwaukee American, Air Canada, Alaska, United, WestJet CAD423
Edmonton to Detroit American, Air Canada, Alaska, United, WestJet CAD375
Edmonton to South Bend Air Canada, Alaska, United, WestJet Check Dates
Edmonton to Minneapolis - St Paul American, Air Canada, Alaska, Spirit, Sun Country, United, WestJet CAD546
Edmonton to Madison American, Air Canada, Alaska, United, WestJet Check Dates
Edmonton to Indianapolis American, Air Canada, Alaska, Allegiant, United, WestJet CAD405
Edmonton to Grand Rapids American, Air Canada, Alaska, Allegiant, United, WestJet CAD602
Edmonton to Atlanta American, Air Canada, Alaska, United, WestJet CAD396
Cheap Flights from Calgary to Chicago, IL, United States, from CAD248 Round trip from YYC to CHI