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MDW - YYC

$99 Find Cheap Flights from Chicago Midway Airport to Calgary

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 1/14. 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
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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 45,397,481 times on KAYAK, and here is why:

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Cheap Flight Deals from Chicago Midway Airport to Calgary (MDW-YYC)

 
These are the cheapest deals for flights from Midway to Calgary currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Calgary

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Calgary.

Recent one-way flight deals from Midway to Calgary

Only flying one-way? Below are some of the best one-way flight deals from Midway to Calgary found on KAYAK recently.

Recent last minute flight deals from Midway to Calgary

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Midway to Calgary.

Recent direct flight deals from Midway to Calgary

The latest deals for direct flights from Midway to Calgary so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Midway to Calgary

Find recent round-trip train or bus tickets from Midway to Calgary.

All round-trip flight deals to Calgary

The cheapest plane tickets to Calgary found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:31 am - 8:35 pmMDW-YYC
12h 04m2 stops
7:00 am - 1:31 pmYYC-MDW
5h 31m1 stop
$259Delta
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Wed, Dec 4 - Tue, Dec 10
9:31 am - 8:35 pmMDW-YYC
12h 04m2 stops
8:00 am - 6:32 pmYYC-MDW
9h 32m2 stops
$264Delta
Find Deal
Wed, Dec 4 - Tue, Dec 10
1:05 pm - 8:04 pmMDW-YYC
7h 59m1 stop
12:30 am - 9:23 amYYC-MDW
7h 53m1 stop
$321Delta
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Wed, Feb 19 - Sat, Feb 22
10:19 am - 7:08 pmMDW-YYC
9h 49m2 stops
7:00 am - 5:47 pmYYC-MDW
9h 47m2 stops
$326Delta
Find Deal
Wed, Jan 8 - Mon, Jan 13
6:07 pm - 11:44 amMDW-YYC
18h 37m1 stop
12:20 pm - 10:45 pmYYC-MDW
9h 25m1 stop
$360
Find Deal
Thu, Nov 28 - Thu, Dec 5
12:43 pm - 10:55 pmMDW-YYC
11h 12m1 stop
9:35 am - 12:13 amYYC-MDW
13h 38m2 stops
$364
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Fri, Dec 6 - Mon, Dec 9
12:05 pm - 9:36 pmMDW-YYC
10h 31m2 stops
7:40 am - 10:20 amYYC-MDW
25h 40m2 stops
$548Porter Airlines
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Fri, Dec 6 - Mon, Dec 9
1:05 pm - 8:04 pmMDW-YYC
7h 59m1 stop
12:30 am - 9:23 amYYC-MDW
7h 53m1 stop
$594WestJet
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Wed, Feb 19 - Sat, Feb 22
11:59 am - 1:50 pmMDW-YYC
26h 51m1 stop
3:00 pm - 6:32 pmYYC-MDW
26h 32m1 stop
$641WestJet
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Thu, Nov 28 - Fri, Dec 6
12:55 pm - 9:36 pmMDW-YYC
9h 41m2 stops
7:40 am - 4:40 pmYYC-MDW
32h 00m2 stops
$718Porter Airlines
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Sat, Dec 14 - Fri, Dec 20
1:26 pm - 8:53 pmMDW-YYC
8h 27m1 stop
$99Delta
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Tue, Jan 14
9:31 am - 8:35 pmMDW-YYC
12h 04m2 stops
$104Delta
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Wed, Dec 4
1:30 pm - 11:09 pmMDW-YYC
10h 39m2 stops
$128Delta
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Thu, Dec 5
9:31 am - 10:30 pmMDW-YYC
13h 59m2 stops
$145Delta
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Tue, Nov 26
6:00 pm - 9:45 pmMDW-YYC
28h 45m2 stops
$161
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Mon, Nov 25
4:45 pm - 5:05 pmMDW-YYC
25h 20m1 stop
$174
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Wed, Nov 13
11:15 am - 11:58 amMDW-YYC
25h 43m1 stop
$234Porter Airlines
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Sun, Nov 24
11:15 am - 3:28 pmMDW-YYC
29h 13m1 stop
$263Porter Airlines
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Fri, Nov 29
7:17 pm - 3:16 pmMDW-YYC
20h 59m2 stops
$380WestJet
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Mon, Nov 18
12:43 pm - 3:16 pmMDW-YYC
27h 33m2 stops
$387WestJet
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Wed, Nov 13
6:30 am - 10:55 pmMDW-YYC
17h 25m2 stops
4:35 pm - 9:37 pmYYC-MDW
28h 02m1 stop
$643
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Fri, Nov 8 - Sun, Nov 10
7:30 am - 8:04 pmMDW-YYC
13h 34m1 stop
4:35 pm - 9:37 pmYYC-MDW
28h 02m1 stop
$696
Find Deal
Fri, Nov 8 - Sun, Nov 10
6:30 am - 10:55 pmMDW-YYC
17h 25m2 stops
12:40 am - 4:40 pmYYC-MDW
15h 00m1 stop
$877
Find Deal
Fri, Nov 8 - Sat, Nov 9
7:30 am - 8:04 pmMDW-YYC
13h 34m1 stop
12:40 am - 4:40 pmYYC-MDW
15h 00m1 stop
$930
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Fri, Nov 8 - Sat, Nov 9
7:55 pm - 7:32 pmMDW-YYC
24h 37m2 stops
9:25 pm - 6:32 pmYYC-MDW
20h 07m2 stops
$977
Find Deal
Fri, Nov 8 - Mon, Nov 11
7:55 pm - 7:32 pmMDW-YYC
24h 37m2 stops
9:25 pm - 6:32 pmYYC-MDW
20h 07m3 stops
$1,107
Find Deal
Fri, Nov 8 - Mon, Nov 11
10:49 am - 7:16 pmMDW-YYC
33h 27m2 stops
6:30 pm - 1:35 pmYYC-MDW
18h 05m2 stops
$1,415WestJet
Find Deal
Fri, Nov 8 - Sun, Nov 10
7:10 pm - 1:35 pmMDW-YYC
19h 25m1 stop
7:00 am - 6:32 pmYYC-MDW
10h 32m1 stop
$1,679WestJet
Find Deal
Fri, Nov 8 - Mon, Nov 11

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 September, where tickets cost $284 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $548 and $400 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 4 days before departure. For the absolute cheapest price, our data suggests you should book 119 days before departure.

Good to know

Cheapest flight

$99
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 $99 for a one-way ticket and $259 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.
1/14Tue
1 stopDelta
8h 27mMDW-YYC
$99
12/4Wed
2 stopsDelta
12h 04mMDW-YYC
$104
12/5Thu
2 stopsDelta
10h 39mMDW-YYC
$128
11/26Tue
2 stopsDelta
13h 59mMDW-YYC
$145
11/25Mon
2 stops
28h 45mMDW-YYC
$161
11/13Wed
1 stop
25h 20mMDW-YYC
$174
11/24Sun
1 stopPorter Airlines
25h 43mMDW-YYC
$234
11/29Fri
1 stopPorter Airlines
29h 13mMDW-YYC
$263
11/18Mon
2 stopsWestJet
20h 59mMDW-YYC
$380
11/13Wed
2 stopsWestJet
27h 33mMDW-YYC
$387

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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.
11/8Fri
multi-stop
17h 25mMDW-YYC
11/10Sun
multi-stop
28h 02mYYC-MDW
$643
11/8Fri
multi-stop
13h 34mMDW-YYC
11/10Sun
multi-stop
28h 02mYYC-MDW
$696
11/8Fri
multi-stop
17h 25mMDW-YYC
11/9Sat
multi-stop
15h 00mYYC-MDW
$877
11/8Fri
multi-stop
13h 34mMDW-YYC
11/9Sat
multi-stop
15h 00mYYC-MDW
$930
11/8Fri
multi-stop
24h 37mMDW-YYC
11/11Mon
multi-stop
20h 07mYYC-MDW
$977
11/8Fri
multi-stop
24h 37mMDW-YYC
11/11Mon
multi-stop
20h 07mYYC-MDW
$1,107
11/8Fri
multi-stopWestJet
33h 27mMDW-YYC
11/10Sun
multi-stopWestJet
18h 05mYYC-MDW
$1,415
11/8Fri
multi-stopWestJet
19h 25mMDW-YYC
11/11Mon
multi-stopWestJet
10h 32mYYC-MDW
$1,679

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Everything you need to know for your flight from Midway to Calgary

Information on your arrival and departure airports

Calgary (YYC)
Chicago Midway Airport (MDW)