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$100+ Cheap flights from Midway (MDW) to Calgary (YYC)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYC
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheap flight deals from Midway to Calgary

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Calgary (YYC). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septiembre 17, 2025.

Round-trip from

$251
(Delta)

One-way from

$100
(Delta)

Popular in

December

Cheapest in

May

Average price

$249
From Chicago Midway to Calgary
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One-way flight from Chicago Midway to Calgary
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Highest demand for flights based on searches. 20% potential increase in price ($76 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Calgary

Cheapest flights from Midway to Calgary
Explore the most affordable flight options available from Midway to Calgary. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.

This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/301:43 pmMDW - YYC
1 stop7h 59mDelta
sáb. 10/46:40 amYYC - MDW
1 stop9h 55mDelta
Deal found 9/16$251
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/306:30 amMDW - YYC
1 stop11h 36mMultiple Airlines
lun. 11/38:15 pmYYC - MDW
2 stops14h 23mMultiple Airlines
Deal found 9/15$254
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/218:05 amMDW - YYC
1 stop12h 55mMultiple Airlines
mar. 10/2112:30 amYYC - MDW
1 stop12h 08mMultiple Airlines
Deal found 9/16$256
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/66:30 amMDW - YYC
1 stop16h 21mMultiple Airlines
lun. 11/1012:30 amYYC - MDW
1 stop10h 08mMultiple Airlines
Deal found 9/15$258
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/1810:00 amMDW - YYC
1 stop9h 21mMultiple Airlines
vie. 10/247:00 amYYC - MDW
2 stops15h 46mMultiple Airlines
Deal found 9/14$259
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/89:20 amMDW - YYC
1 stop5h 34mDelta
sáb. 11/156:20 amYYC - MDW
2 stops10h 48mDelta
Deal found 9/15$261
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/61:37 pmMDW - YYC
1 stop23h 07mMultiple Airlines
dom. 11/98:15 pmYYC - MDW
2 stops21h 24mMultiple Airlines
Deal found 9/16$277
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/61:48 pmMDW - YYC
1 stop7h 59mDelta
sáb. 10/186:45 amYYC - MDW
1 stop5h 23mDelta
Deal found 9/15$279

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Calgary that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Calgary that are best for you.

Fly from

Midway

Fly to

Calgary

Route

Depart

Return

Price

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

sáb. 10/11

3:00 pm-8:47 pm

1 stop6h 47m

Calgary

sáb. 10/18

6:45 am-1:08 pm

1 stop5h 23m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

mar. 9/30

1:43 pm-8:42 pm

1 stop7h 59m

Calgary

sáb. 10/4

6:40 am-5:35 pm

1 stop9h 55m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

sáb. 10/18

9:20 am-1:54 pm

1 stop5h 34m

Calgary

vie. 10/24

6:45 am-5:43 pm

1 stop9h 58m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

sáb. 11/8

3:00 pm-8:47 pm

1 stop6h 47m

Calgary

sáb. 11/15

6:20 am-1:07 pm

1 stop5h 47m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

mar. 9/30

1:43 pm-8:42 pm

1 stop7h 59m

Calgary

vie. 10/3

6:40 am-5:35 pm

1 stop9h 55m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

lun. 9/29

9:20 am-1:32 pm

1 stop5h 12m

Calgary

jue. 10/2

6:40 am-5:35 pm

1 stop9h 55m

$289

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

sáb. 9/27

1:43 pm-8:42 pm

1 stop7h 59m

Calgary

mié. 10/1

6:40 am-5:35 pm

1 stop9h 55m

$289

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

lun. 9/29

1:43 pm-8:42 pm

1 stop7h 59m

Calgary

mié. 10/1

6:40 am-5:35 pm

1 stop9h 55m

$289

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

mar. 9/30

1:43 pm-8:42 pm

1 stop7h 59m

$100

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

jue. 10/30

9:20 am-1:54 pm

1 stop5h 34m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 18 results
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Best time to book a flight from Midway to Calgary

Have a flexible travel schedule? Discover the best time to fly to Calgary from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Calgary

What is the cheapest time of day to fly from MDW to YYC?

Find hourly flight availability from Midway to Calgary. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 17, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 51% on flights from Chicago Midway Airport to Calgary by exploring options for tickets in the morning.

Related info for your journey

Find useful and relevant information for your journey from Midway to Calgary. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Calgary from Chicago Midway?

    Most people fly into Calgary (YYC) if they book a flight to Calgary from Chicago Midway. On average, Calgary has 0 inbound flights from Chicago Midway per day from 0 airlines. Calgary is conveniently located just 5.8 mi from Calgary’s city center.

  • How long is the flight from Chicago Midway Airport to Calgary?

    A quick flight from Chicago Midway Airport to Calgary can take about 6h 47m. Delta provides one of the quickest options available for as low as $251. Airlines will cover a distance of 1396 mi.

  • Can I find deals for flights from Midway to Calgary that include hotel bookings?

    Yes. In addition to deals on Midway to Calgary flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Calgary?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Calgary.

  • Can I find deals for business class flights from Midway to Calgary?

    Yes. Cheapflights offers flight deals from Midway to Calgary by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Calgary (average of $300). Flying from Chicago Midway Airport to Calgary in February is currently the most expensive (average of $405). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Canmore
Airdrie

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