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$131+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYC
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$252
(Delta)

One-way from

$131
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$337
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 ($83 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 July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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 9/271:43 pmMDW - YYC
1 stop7h 59mDelta
Sat 10/46:40 amYYC - MDW
1 stop9h 55mDelta
Deal found 7/29$252
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 9/179:00 amMDW - YYC
1 stop12h 00mMultiple Airlines
Mon 9/2212:30 amYYC - MDW
1 stop14h 28mMultiple Airlines
Deal found 7/26$285

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 July 29, 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

Sat 9/27

1:43 pm-8:42 pm

1 stop7h 59m

Calgary

Sat 10/4

6:40 am-5:35 pm

1 stop9h 55m

$252

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 9/17

9:00 am-8:00 pm

1 stop12h 00m

Calgary

Mon 9/22

12:30 am-3:58 pm

1 stop14h 28m

$285

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 9/29

7:03 pm-11:55 am

1 stop17h 52m

$131

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 9/13

9:20 am-6:40 pm

2 stops10h 20m

$137

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 9/15

9:15 am-10:28 pm

2 stops14h 13m

$138

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 9/16

9:20 am-10:22 pm

2 stops14h 02m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 July 29, 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.

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 July 29, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta, and WestJet from Chicago Midway Airport to Calgary to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
317 reviews
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,977 reviews
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,973 reviews
Porter Airlines
8.0
Very good
317 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 to fly from Chicago Midway Airport to Calgary one-way?

    $137 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 $138 and $240, 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 February is currently the most expensive (average of $402). 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

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