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$123+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYC
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Find cheap flights from Midway to Calgary with Cheapflights

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2. Select your favorite providers

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3. Compare prices and book

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Cheap 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 January 20, 2026.

This Delta deal was found by Cheapflights users on 1/18. 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 2/249:50 am
MDW
-
YYC
2 stops14h 15m
Delta
Thu 3/56:30 am
YYC
-
MDW
1 stop5h 35m
Delta
Deal found 1/18$265
This Delta deal was found by Cheapflights users on 1/19. 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 4/152:12 pm
MDW
-
YYC
1 stop7h 28m
Delta
Sun 4/196:40 am
YYC
-
MDW
1 stop5h 52m
Delta
Deal found 1/19$267
This Delta deal was found by Cheapflights users on 1/18. 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 2/249:50 am
MDW
-
YYC
2 stops14h 15m
Delta
Wed 3/46:30 am
YYC
-
MDW
2 stops10h 07m
Delta
Deal found 1/18$270
This Delta deal was found by Cheapflights users on 1/18. 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.
Thu 2/269:50 am
MDW
-
YYC
2 stops14h 15m
Delta
Thu 3/56:30 am
YYC
-
MDW
1 stop5h 35m
Delta
Deal found 1/18$277
This Delta deal was found by Cheapflights users on 1/19. 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.
Tue 2/171:49 pm
MDW
-
YYC
1 stop8h 05m
Delta
Thu 2/266:30 am
YYC
-
MDW
1 stop5h 35m
Delta
Deal found 1/19$278
This Delta deal was found by Cheapflights users on 1/18. 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.
Thu 2/269:50 am
MDW
-
YYC
2 stops14h 15m
Delta
Wed 3/46:30 am
YYC
-
MDW
2 stops10h 07m
Delta
Deal found 1/18$282
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Wed 2/187:00 am
MDW
-
YYC
1 stop13h 09m
Multiple Airlines
Sat 2/217:35 pm
YYC
-
MDW
1 stop27h 06m
Multiple Airlines
Deal found 1/19$286
This Delta deal was found by Cheapflights users on 1/19. 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.
Tue 2/179:34 am
MDW
-
YYC
2 stops12h 20m
Delta
Fri 2/276:30 am
YYC
-
MDW
2 stops10h 07m
Delta
Deal found 1/19$293
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Wed 2/187:00 am
MDW
-
YYC
1 stop13h 09m
Multiple Airlines
Wed 2/257:00 pm
YYC
-
MDW
2 stops20h 16m
Multiple Airlines
Deal found 1/19$296
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Wed 2/187:00 am
MDW
-
YYC
1 stop13h 09m
Multiple Airlines
Mon 2/2312:30 am
YYC
-
MDW
1 stop17h 37m
Multiple Airlines
Deal found 1/19$298
This Delta deal was found by Cheapflights users on 1/19. 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.
Tue 2/171:49 pm
MDW
-
YYC
1 stop8h 05m
Delta
Mon 2/237:40 am
YYC
-
MDW
2 stops10h 00m
Delta
Deal found 1/19$300

Find 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 January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$265
(Delta)

One-way from

$123
(Trip.com)

Popular in

December

Cheapest in

May

Average price

$229
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. 4% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 20, 2026.
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

Sat 2/28

11:45 am-11:05 pm

2 stops12h 20m

Calgary

Tue 3/3

6:30 am-1:05 pm

1 stop5h 35m

$265

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/24

9:50 am-11:05 pm

2 stops14h 15m

Calgary

Thu 3/5

6:30 am-1:05 pm

1 stop5h 35m

$265

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/24

9:50 am-11:05 pm

2 stops14h 15m

Calgary

Tue 3/3

6:30 am-1:05 pm

1 stop5h 35m

$265

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 3/3

9:34 am-8:54 pm

2 stops12h 20m

Calgary

Tue 3/10

6:30 am-1:25 pm

1 stop5h 55m

$265

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/28

11:45 am-11:05 pm

2 stops12h 20m

Calgary

Thu 3/5

6:30 am-1:05 pm

1 stop5h 35m

$265

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/24

9:50 am-11:05 pm

2 stops14h 15m

Calgary

Thu 2/26

6:30 am-5:37 pm

2 stops10h 07m

$270

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/7

11:45 am-8:54 pm

1 stop10h 09m

Calgary

Tue 3/3

6:30 am-1:05 pm

1 stop5h 35m

$273

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/7

11:45 am-8:54 pm

1 stop10h 09m

Calgary

Wed 3/4

6:30 am-1:05 pm

1 stop5h 35m

$273

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/17

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Thu 2/26

6:30 am-1:05 pm

1 stop5h 35m

$278

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/17

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Wed 2/25

6:30 am-1:05 pm

1 stop5h 35m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 20 results
1
2

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Calgary flight deals on Cheapflights vs. FlightHub >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 Expedia the most. Expedia 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.

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 12h 20m. Delta provides one of the quickest options available for as low as $265. 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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