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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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYC
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$250
(Delta)

One-way from

$105
(Delta)

Popular in

December

Cheapest in

May

Average price

$278
Provider with most accurate pricing for Chicago Midway-Calgary flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Calgary flights.
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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. 23% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 15, 2025.

This Delta deal was found by Cheapflights users on 4/15. 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.
Tue 5/61:16 pmMDW - YYC
1 stop8h 31mDelta
Thu 5/86:30 amYYC - MDW
1 stop10h 15mDelta
Deal found 4/15$250
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Sat 6/146:20 amMDW - YYC
1 stop16h 55mMultiple Airlines
Tue 6/1712:30 amYYC - MDW
1 stop9h 11mMultiple Airlines
Deal found 4/14$302
This Mytrip deal was found by Cheapflights users on 4/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/119:40 amMDW - YYC
2 stops12h 35mPorter Airlines
Wed 7/1611:55 pmYYC - MDW
2 stops15h 29mPorter Airlines
Deal found 4/14$548
This Trip.com deal was found by Cheapflights users on 4/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/221:05 pmMDW - YYC
1 stop7h 55mWestJet
Tue 7/2910:00 amYYC - MDW
1 stop10h 47mWestJet
Deal found 4/15$714

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 April 15, 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 5/6

1:16 pm-8:47 pm

1 stop8h 31m

Calgary

Thu 5/8

6:30 am-5:45 pm

1 stop10h 15m

$250

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 6/14

6:20 am-10:15 pm

1 stop16h 55m

Calgary

Tue 6/17

12:30 am-10:41 am

1 stop9h 11m

$302

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 5/12

9:40 am-10:30 pm

2 stops13h 50m

Calgary

Tue 5/13

7:00 am-4:54 pm

2 stops32h 54m

$502

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 7/2

12:44 pm-8:00 pm

1 stop8h 16m

Calgary

Mon 7/7

12:30 am-9:51 am

1 stop8h 21m

$713

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 5/13

1:55 pm-11:01 pm

2 stops10h 06m

$105

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 6/7

9:59 am-8:05 pm

1 stop11h 06m

$118

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 5/30

5:50 pm-10:30 pm

2 stops29h 40m

$280

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 7/5

12:44 pm-8:00 pm

1 stop8h 16m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
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 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 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 April 15, 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.

Rainfall in Calgary by month

Plan your trip to Calgary by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Calgary ranges from 0.4 - 3.7 inches per month. June is typically the wettest month, when rainfall can reach 3.7 in. January is typically the driest time to visit Calgary when rainfall is around 0.4 in.

Temperature in Calgary by month

Plan your trip to Calgary by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Calgary, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 62.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

Reviews of airlines servicing Calgary

Get insights into the airlines that provide service to Calgary. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Calgary. Reviews last updated April 15, 2025.
Porter Airlines
8.0
Very good
281 reviews

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
8.0
Very good
281 reviews
Porter Airlines
8.0
Very good
281 reviews

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Delta
8.0
Very good
7,918 reviews
Porter Airlines
8.0
Very good
281 reviews

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
WestJet
7.2
Good
2,805 reviews
Porter Airlines
8.0
Very good
281 reviews

Crew

8.7

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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.

  • What are the cheapest airlines flying from Chicago Midway Airport to Calgary round-trip?

    Delta, at $250, was found to be the cheapest airline from Chicago Midway Airport to Calgary.Alternate airlines to your destination round-trip include Porter Airlines and WestJet.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Calgary one-way?

    $105 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Porter Airlines and WestJet, with prices starting from $280 and $372, respectively.

  • 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 June is currently the most expensive (average of $410). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Canmore
Airdrie

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