HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Calgary

$112+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYC
May 8 — May 151
Fri 5/8
Fri 5/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Calgary with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/5. 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.
Tue 4/282:15 pm
MDW
-
YYC
2 stops26h 00m
Multiple Airlines
Sat 5/27:00 am
YYC
-
MDW
1 stop10h 37m
Multiple Airlines
Deal found 4/5$319
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
Mon 4/202:15 pm
MDW
-
YYC
1 stop22h 28m
Multiple Airlines
Tue 9/112:30 am
YYC
-
MDW
1 stop9h 39m
Multiple Airlines
Deal found 4/6$327
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/27:34 pm
MDW
-
YYC
1 stop16h 26m
Multiple Airlines
Mon 5/46:30 pm
YYC
-
MDW
2 stops15h 39m
Multiple Airlines
Deal found 4/6$328
This Kiwi.com deal was found by Cheapflights users on 4/7. 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.
Tue 5/56:00 am
MDW
-
YYC
1 stop12h 10m
Multiple Airlines
Mon 5/1112:30 am
YYC
-
MDW
1 stop9h 39m
Multiple Airlines
Deal found 4/7$329
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
Fri 5/12:15 pm
MDW
-
YYC
1 stop21h 45m
Multiple Airlines
Mon 5/46:30 pm
YYC
-
MDW
2 stops15h 39m
Multiple Airlines
Deal found 4/6$332
This Delta deal was found by Cheapflights users on 4/7. 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 5/69:27 am
MDW
-
YYC
2 stops12h 13m
Delta
Wed 5/136:45 am
YYC
-
MDW
1 stop10h 11m
Delta
Deal found 4/7$338
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/302:15 pm
MDW
-
YYC
1 stop21h 45m
Multiple Airlines
Sat 5/29:00 pm
YYC
-
MDW
2 stops24h 19m
Multiple Airlines
Deal found 4/6$340
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
Fri 5/12:15 pm
MDW
-
YYC
1 stop21h 45m
Multiple Airlines
Sat 5/29:00 pm
YYC
-
MDW
2 stops24h 19m
Multiple Airlines
Deal found 4/6$345

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 April 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(Kiwi.com)

One-way from

$112
(Delta)

Popular in

December

Cheapest in

January

Average price

$379
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, 5% 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 April 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 April 8, 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

Tue 6/2

1:22 pm-8:05 pm

1 stop7h 43m

Calgary

Sun 6/7

6:45 am-1:09 pm

1 stop5h 24m

$417

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 5/4

1:24 pm-8:05 pm

1 stop7h 41m

Calgary

Mon 5/11

6:45 am-5:56 pm

1 stop10h 11m

$417

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 5/1

1:24 pm-8:05 pm

1 stop7h 41m

Calgary

Sat 5/9

6:45 am-1:19 pm

1 stop5h 34m

$418

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-1:19 pm

1 stop5h 34m

$433

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/16

9:22 am-8:30 pm

2 stops12h 08m

Calgary

Sun 5/24

6:45 am-1:19 pm

1 stop5h 34m

$433
Quickest round-trip

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/2

2:12 pm-8:40 pm

1 stop7h 28m

Calgary

Sat 5/9

6:45 am-1:19 pm

1 stop5h 34m

$435

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 4/28

9:27 am-8:40 pm

2 stops12h 13m

Calgary

Sat 5/2

7:40 am-10:28 pm

2 stops13h 48m

$438

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 6/2

1:22 pm-8:05 pm

1 stop7h 43m

Calgary

Tue 6/9

6:45 am-1:09 pm

1 stop5h 24m

$454

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 9/1

1:00 pm-8:05 pm

1 stop8h 05m

Calgary

Sun 9/6

6:35 am-1:11 pm

1 stop5h 36m

$471

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 7/14

11:05 am-9:50 pm

1 stop11h 45m

Calgary

Sat 7/25

6:45 am-5:52 pm

1 stop10h 07m

$496

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 17 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 April.
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 43m. Delta provides one of the quickest options available for as low as $417. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Calgary

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Calgary flights
O'Hare Intl to Edmonton flights
O'Hare Intl to Grande Prairie flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights