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MDW - YYC

Find cheap flights from Chicago Midway Airport to Calgary from $329

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Calgary departing on 6/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Tue 5/28
Tue 6/4

Search hundreds of travel sites at once for deals on flights to Calgary

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Calgary, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Calgary, as well as popular online travel agencies
In the last 7 days travelers have searched 43,623,357 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Midway to Calgary (MDW-YYC)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Calgary that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:32 am - 9:59 pmMDW-YYC
11h 27m1 stop
12:30 am - 1:55 pmYYC-MDW
12h 25m1 stop
$345
Find Deal
Sat, Jul 27 - Mon, Jul 29
10:00 am - 7:59 pmMDW-YYC
10h 59m1 stop
12:30 am - 1:55 pmYYC-MDW
12h 25m1 stop
$366
Find Deal
Thu, Jul 25 - Mon, Jul 29
10:59 pm - 2:39 pmMDW-YYC
16h 40m1 stop
12:30 am - 2:41 pmYYC-MDW
13h 11m1 stop
$370
Find Deal
Tue, May 14 - Sun, May 19
7:27 am - 7:59 pmMDW-YYC
13h 32m1 stop
12:30 am - 1:55 pmYYC-MDW
12h 25m1 stop
$371
Find Deal
Wed, Jul 24 - Mon, Jul 29
9:20 am - 1:51 pmMDW-YYC
5h 31m1 stop
6:50 am - 6:05 pmYYC-MDW
10h 15m1 stop
$529Delta
Find Deal
Tue, Oct 1 - Sun, Oct 6
11:59 am - 8:43 pmMDW-YYC
9h 44m1 stop
6:50 am - 6:05 pmYYC-MDW
10h 15m1 stop
$536Delta
Find Deal
Sat, Sep 14 - Sun, Sep 22
9:35 am - 8:43 pmMDW-YYC
12h 08m2 stops
6:50 am - 1:02 pmYYC-MDW
5h 12m1 stop
$539Delta
Find Deal
Tue, Oct 1 - Sun, Oct 6
8:00 am - 10:09 pmMDW-YYC
15h 09m2 stops
7:35 am - 9:37 pmYYC-MDW
13h 02m2 stops
$541Porter Airlines
Find Deal
Fri, Jun 7 - Wed, Jun 12
5:15 pm - 11:34 amMDW-YYC
19h 19m2 stops
7:35 am - 9:37 pmYYC-MDW
13h 02m2 stops
$721Porter Airlines
Find Deal
Thu, Jun 13 - Wed, Jun 19
8:00 am - 9:05 pmMDW-YYC
14h 05m2 stops
7:35 am - 9:37 pmYYC-MDW
13h 02m2 stops
$741Porter Airlines
Find Deal
Mon, Jun 24 - Thu, Jun 27

Flights from Midway to Calgary - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Calgary to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Calgary?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Calgary, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Calgary is October, where tickets cost $288 on average. On the other hand, the most expensive months are December and February, where the average cost of tickets is $533 and $497 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Calgary?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Calgary, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Calgary, you should book around 2 days before departure. For the absolute cheapest price, our data suggests you should book 88 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Calgary?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Calgary from Chicago Midway Airport were found on Delta ($329) and WestJet ($638), and the lowest round-trip tickets were found on Delta ($529) and Porter Airlines ($541).

Good to know

Cheapest flight

$329
Flight from Chicago Midway Airport to Calgary

When to book flights from Midway to Calgary

Are your dates flexible? Find out the best times to travel from Midway to Calgary based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Calgary flights

  • What is the cheapest flight from Chicago Midway Airport to Calgary?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Calgary was $329 for a one-way ticket and $345 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Calgary?

    Yes, you’ll need a passport to travel to Calgary from Chicago Midway Airport.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Calgary?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Calgary?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Calgary.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Calgary?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Calgary.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Calgary?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Calgary from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Calgary?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Calgary with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and YYC can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Calgary?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Calgary from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from Chicago to Calgary

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Calgary found on KAYAK in the last 72 hours.
6/30Sun
1 stopDelta
9h 19mMDW-YYC
$329
6/30Sun
2 stops
12h 42mMDW-YYC
$353
5/30Thu
1 stopDelta
8h 16mMDW-YYC
$422
5/30Thu
2 stopsWestJet
14h 35mMDW-YYC
$638
5/27Mon
2 stopsWestJet
13h 03mMDW-YYC
$666
5/22Wed
2 stopsWestJet
13h 34mMDW-YYC
$789
6/17Mon
2 stopsWestJet
10h 50mMDW-YYC
$797
6/22Sat
2 stopsWestJet
10h 50mMDW-YYC
$801
5/9Thu
2 stopsDelta
9h 26mMDW-YYC
$872
5/20Mon
2 stopsWestJet
13h 03mMDW-YYC
$918

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Last minute flights from Midway to Calgary

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Calgary that are departing in the next 10 days.
5/1Wed
multi-stopDelta
10h 36mMDW-YYC
5/12Sun
multi-stopDelta
9h 12mYYC-MDW
$432
5/1Wed
multi-stop
25h 11mMDW-YYC
5/11Sat
multi-stop
12h 23mYYC-MDW
$451
5/1Wed
multi-stop
25h 11mMDW-YYC
5/3Fri
multi-stop
27h 39mYYC-MDW
$460
5/1Wed
multi-stop
18h 40mMDW-YYC
5/3Fri
multi-stop
27h 39mYYC-MDW
$498
5/1Wed
multi-stopDelta
10h 36mMDW-YYC
5/12Sun
multi-stopDelta
10h 42mYYC-MDW
$513
5/1Wed
multi-stop
18h 40mMDW-YYC
5/2Thu
multi-stop
13h 09mYYC-MDW
$546
5/1Wed
multi-stopDelta
12h 56mMDW-YYC
5/12Sun
multi-stopDelta
10h 42mYYC-MDW
$638
5/1Wed
multi-stop
13h 59mMDW-YYC
5/11Sat
multi-stop
16h 53mYYC-MDW
$668
5/1Wed
multi-stopPorter Airlines
11h 54mMDW-YYC
5/3Fri
multi-stopPorter Airlines
11h 47mYYC-MDW
$1,614
5/1Wed
multi-stopWestJet
25h 57mMDW-YYC
5/2Thu
multi-stopWestJet
10h 35mYYC-MDW
$1,765

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Chicago Midway Airport - Calgary Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Calgary (YYC)Canada

Return flight deals:

Calgary - Chicago Midway Airport

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