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$105+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYC
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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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 November 20, 2025.

This Delta deal was found by Cheapflights users on 11/19. 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.
Wed 12/101:50 pmMDW - YYC
1 stop8h 07mDelta
Sat 12/136:35 amYYC - MDW
1 stop5h 35mDelta
Deal found 11/19$251
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 11/276:05 amMDW - YYC
1 stop14h 04mMultiple Airlines
Mon 12/19:45 pmYYC - MDW
2 stops34h 01mMultiple Airlines
Deal found 11/19$259
This Delta deal was found by Cheapflights users on 11/18. 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 12/91:50 pmMDW - YYC
1 stop8h 07mDelta
Fri 12/126:35 amYYC - MDW
2 stops10h 25mDelta
Deal found 11/18$261
This Delta deal was found by Cheapflights users on 11/19. 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.
Wed 11/261:47 pmMDW - YYC
1 stop8h 06mDelta
Wed 12/106:35 amYYC - MDW
1 stop5h 35mDelta
Deal found 11/19$283
This Delta deal was found by Cheapflights users on 11/19. 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.
Wed 11/261:47 pmMDW - YYC
1 stop8h 06mDelta
Sun 12/76:35 amYYC - MDW
1 stop5h 35mDelta
Deal found 11/19$315
This Delta deal was found by Cheapflights users on 11/19. 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.
Wed 11/269:41 amMDW - YYC
2 stops14h 29mDelta
Tue 12/96:35 amYYC - MDW
1 stop5h 35mDelta
Deal found 11/19$325
This Delta deal was found by Cheapflights users on 11/19. 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.
Wed 11/266:00 amMDW - YYC
2 stops15h 53mDelta
Mon 12/87:35 amYYC - MDW
2 stops9h 43mDelta
Deal found 11/19$330
This Delta deal was found by Cheapflights users on 11/19. 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.
Thu 11/279:34 amMDW - YYC
2 stops29h 19mDelta
Wed 12/106:35 amYYC - MDW
1 stop5h 35mDelta
Deal found 11/19$336

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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$235
(Kiwi.com)

One-way from

$105
(Delta)

Popular in

December

Cheapest in

October

Average price

$250
Provider with most accurate pricing for Chicago Midway-Calgary flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Calgary flights.
Search Deals
From Chicago Midway to Calgary
Search Deals
One-way flight from Chicago Midway to Calgary
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 20, 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

Tue 1/20

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Sat 1/24

6:30 am-4:16 pm

1 stop8h 46m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 1/26

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Fri 1/30

6:30 am-1:09 pm

1 stop5h 39m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 1/25

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Sat 1/31

6:30 am-4:16 pm

1 stop8h 46m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 1/18

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Wed 1/28

6:30 am-1:09 pm

1 stop5h 39m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 1/20

11:05 am-12:05 am

1 stop14h 00m

Calgary

Sat 1/24

9:45 pm-11:45 am

2 stops13h 00m

$255

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 12/9

10:49 am-11:13 pm

2 stops13h 24m

Calgary

Fri 12/12

6:35 am-6:00 pm

2 stops10h 25m

$266

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 12/10

1:50 pm-8:57 pm

1 stop8h 07m

Calgary

Sat 12/13

6:35 am-1:10 pm

1 stop5h 35m

$283

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/17

1:49 pm-8:56 pm

1 stop8h 07m

Calgary

Thu 2/19

6:30 am-1:09 pm

1 stop5h 39m

$306

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 1/21

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Sat 1/31

6:30 am-4:16 pm

1 stop8h 46m

$306

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 1/21

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Wed 1/28

6:30 am-1:09 pm

1 stop5h 39m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 22 results
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Compare providers for flights from Midway to Calgary

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Calgary in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Calgary flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Calgary flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Calgary flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Calgary flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Calgary flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 November 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 50% 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 8h 05m. 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.

See more FAQs

Traveling to a place near Calgary?

Book flights to Calgary if you plan to visit one of these locations
Canmore
Airdrie

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