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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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYC
Apr 10 — Apr 171
Fri 4/10
Fri 4/17
1 adult, Economy
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Find cheap flights from Midway to Calgary with Cheapflights

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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 March 11, 2026.

This Delta deal was found by Cheapflights users on 3/9. 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.
Wed 5/271:59 pm
MDW
-
YYC
1 stop7h 31m
Delta
Sun 5/316:45 am
YYC
-
MDW
1 stop5h 34m
Delta
Deal found 3/9$286
This Delta deal was found by Cheapflights users on 3/8. 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 5/29:27 am
MDW
-
YYC
2 stops12h 13m
Delta
Sat 5/96:45 am
YYC
-
MDW
1 stop5h 34m
Delta
Deal found 3/8$294
This Delta deal was found by Cheapflights users on 3/8. 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.
Sun 5/249:22 am
MDW
-
YYC
2 stops12h 08m
Delta
Tue 6/26:45 am
YYC
-
MDW
1 stop10h 11m
Delta
Deal found 3/8$297
This Delta deal was found by Cheapflights users on 3/8. 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.
Sun 5/249:22 am
MDW
-
YYC
2 stops12h 08m
Delta
Sat 5/307:45 am
YYC
-
MDW
2 stops9h 48m
Delta
Deal found 3/8$302
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:59 pm
MDW
-
YYC
1 stop7h 31m
Delta
Tue 6/26:45 am
YYC
-
MDW
1 stop10h 11m
Delta
Deal found 3/10$306
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Sat 4/257:34 pm
MDW
-
YYC
1 stop16h 26m
Multiple Airlines
Tue 4/2812:30 am
YYC
-
MDW
1 stop18h 01m
Multiple Airlines
Deal found 3/10$307
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:59 pm
MDW
-
YYC
1 stop7h 31m
Delta
Sat 5/306:45 am
YYC
-
MDW
1 stop5h 34m
Delta
Deal found 3/10$309
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/86:00 am
MDW
-
YYC
1 stop14h 09m
Multiple Airlines
Tue 4/1412:30 am
YYC
-
MDW
1 stop18h 01m
Multiple Airlines
Deal found 3/10$314
This Delta deal was found by Cheapflights users on 3/8. 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.
Sun 5/249:22 am
MDW
-
YYC
2 stops12h 08m
Delta
Wed 6/36:45 am
YYC
-
MDW
1 stop5h 34m
Delta
Deal found 3/8$325
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/227:30 am
MDW
-
YYC
2 stops15h 00m
Multiple Airlines
Wed 4/297:00 am
YYC
-
MDW
1 stop11h 31m
Multiple Airlines
Deal found 3/8$326
This Delta deal was found by Cheapflights users on 3/8. 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.
Sun 5/249:22 am
MDW
-
YYC
2 stops12h 08m
Delta
Fri 6/56:45 am
YYC
-
MDW
1 stop10h 11m
Delta
Deal found 3/8$328

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 March 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$286
(Delta)

One-way from

$105
(Delta)

Popular in

December

Cheapest in

January

Average price

$348
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
High demand for flights, 3% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Calgary that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 5/27

1:59 pm-8:30 pm

1 stop7h 31m

Calgary

Fri 5/29

6:45 am-5:56 pm

1 stop10h 11m

$309

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/9

9:22 am-8:30 pm

2 stops12h 08m

Calgary

Sat 5/30

6:45 am-1:19 pm

1 stop5h 34m

$369

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 5/27

9:22 am-8:30 pm

2 stops12h 08m

Calgary

Wed 6/3

6:45 am-1:19 pm

1 stop5h 34m

$376

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/2

9:27 am-8:40 pm

2 stops12h 13m

Calgary

Sat 5/9

6:45 am-9:09 pm

2 stops13h 24m

$384
Quickest round-trip

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 5/26

1:59 pm-8:30 pm

1 stop7h 31m

Calgary

Sun 5/31

6:45 am-1:19 pm

1 stop5h 34m

$385

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/16

9:22 am-8:30 pm

2 stops12h 08m

Calgary

Sat 5/23

6:45 am-5:56 pm

1 stop10h 11m

$400

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 6/3

1:22 pm-8:05 pm

1 stop7h 43m

Calgary

Sun 6/7

6:35 am-1:07 pm

1 stop5h 32m

$451

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 5/1

1:24 pm-8:05 pm

1 stop7h 41m

Calgary

Sat 5/9

7:45 am-6:33 pm

2 stops9h 48m

$461

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 5/1

1:24 pm-8:05 pm

1 stop7h 41m

Calgary

Mon 5/4

11:00 am-5:58 pm

1 stop5h 58m

$471

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 4/23

9:27 am-7:28 pm

2 stops11h 01m

Calgary

Wed 4/29

7:00 am-6:36 pm

2 stops10h 36m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 20 resultsSorted by cheapest first
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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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 FlightHub the most. FlightHub 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 7h 31m. Delta provides one of the quickest options available for as low as $309. 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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