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$94+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYC
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$224
(Kiwi.com)

One-way from

$100
(Delta)

Popular in

December

Cheapest in

May

Average price

$258
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. 21% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Wed 10/228:05 amMDW - YYC
2 stops17h 39mMultiple Airlines
Fri 10/245:30 pmYYC - MDW
1 stop21h 39mMultiple Airlines
Deal found 9/9$224
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sat 10/1110:00 amMDW - YYC
1 stop9h 21mMultiple Airlines
Tue 10/1412:30 amYYC - MDW
1 stop12h 08mMultiple Airlines
Deal found 9/9$235
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 10/66:20 amMDW - YYC
1 stop14h 40mMultiple Airlines
Tue 10/1412:30 amYYC - MDW
1 stop12h 08mMultiple Airlines
Deal found 9/9$237
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Wed 10/158:05 amMDW - YYC
2 stops17h 39mMultiple Airlines
Fri 10/175:30 pmYYC - MDW
1 stop21h 39mMultiple Airlines
Deal found 9/10$245
This Delta deal was found by Cheapflights users on 9/9. 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.
Tue 10/79:20 amMDW - YYC
1 stop5h 34mDelta
Sat 10/186:45 amYYC - MDW
1 stop9h 58mDelta
Deal found 9/9$251
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Mon 10/2010:56 pmMDW - YYC
1 stop14h 16mMultiple Airlines
Tue 10/2112:30 amYYC - MDW
1 stop12h 08mMultiple Airlines
Deal found 9/10$252
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 11/811:10 amMDW - YYC
2 stops12h 52mDelta
Sat 11/156:20 amYYC - MDW
1 stop5h 47mDelta
Deal found 9/11$261
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Thu 11/66:25 amMDW - YYC
1 stop13h 44mMultiple Airlines
Mon 11/1012:30 amYYC - MDW
1 stop10h 08mMultiple Airlines
Deal found 9/10$265

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 September 11, 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

Wed 10/8

1:48 pm-8:47 pm

1 stop7h 59m

Calgary

Sun 10/12

6:45 am-5:43 pm

1 stop9h 58m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/8

1:48 pm-8:47 pm

1 stop7h 59m

Calgary

Sat 10/18

6:45 am-5:43 pm

1 stop9h 58m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

1:06 pm-8:47 pm

2 stops8h 41m

Calgary

Sat 11/15

6:20 am-1:07 pm

1 stop5h 47m

$261

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 11/6

6:25 am-7:09 pm

1 stop13h 44m

Calgary

Mon 11/10

12:30 am-11:38 am

1 stop10h 08m

$265

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/8

1:48 pm-8:47 pm

1 stop7h 59m

Calgary

Fri 10/17

6:45 am-5:43 pm

1 stop9h 58m

$268

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 10/11

9:20 am-11:02 pm

2 stops14h 42m

Calgary

Fri 10/17

6:45 am-5:43 pm

1 stop9h 58m

$278

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/8

9:35 am-6:24 pm

1 stop9h 49m

Calgary

Wed 10/15

9:15 am-6:25 pm

1 stop8h 10m

$294

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 10/6

10:35 am-8:00 pm

1 stop10h 25m

Calgary

Sat 10/11

9:15 am-6:25 pm

1 stop8h 10m

$294

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 10/24

1:48 pm-8:47 pm

1 stop7h 59m

Calgary

Tue 10/28

6:45 am-5:43 pm

1 stop9h 58m

$295

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 10/11

9:20 am-6:40 pm

2 stops10h 20m

Calgary

Wed 10/15

9:15 am-6:25 pm

1 stop8h 10m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 19 results
1
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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 September 11, 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 7h 59m. 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

Traveling to a place near Calgary?

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Canmore
Airdrie

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