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$130+ Cheap flights from Alberta to Midway (MDW)

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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Alberta to Midway

Keep the following information in mind while searching for Alberta to Midway flight deals. Data was last updated September 11, 2025.

Round-trip from

$223
(Delta)

One-way from

$130
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$230
From Alberta to Chicago Midway
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One-way flight from Alberta to Chicago Midway
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Highest demand for flights based on searches. 23% potential increase in price ($87 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Alberta to Midway

Cheapest flights from Alberta to Midway
Explore the most affordable flight options available from Alberta to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 10/256:45 amYYC - MDW
1 stop5h 23mDelta
Sat 11/19:20 amMDW - YYC
1 stop5h 34mDelta
Deal found 9/10$223
This Delta deal was found by Cheapflights users on 9/9. 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 10/299:15 amYEG - MDW
1 stop7h 28mDelta
Sat 11/19:20 amMDW - YEG
2 stops9h 00mDelta
Deal found 9/9$224
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:00 amYYC - MDW
2 stops15h 46mMultiple Airlines
Thu 10/2310:30 amMDW - YYC
1 stop8h 51mMultiple Airlines
Deal found 9/9$227
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:00 amYYC - MDW
2 stops29h 38mMultiple Airlines
Tue 10/148:05 amMDW - YYC
1 stop28h 14mMultiple Airlines
Deal found 9/9$230
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:00 amYYC - MDW
2 stops15h 46mMultiple Airlines
Fri 10/316:30 amMDW - YYC
1 stop11h 36mMultiple Airlines
Deal found 9/9$231
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:30 pmYYC - MDW
1 stop21h 39mMultiple Airlines
Mon 10/209:44 amMDW - YYC
1 stop26h 35mMultiple Airlines
Deal found 9/9$233
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:00 amYYC - MDW
2 stops12h 21mMultiple Airlines
Thu 10/306:20 amMDW - YYC
1 stop13h 49mMultiple Airlines
Deal found 9/9$235
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 10/189:25 amYEG - MDW
2 stops11h 49mDelta
Sat 10/253:00 pmMDW - YEG
2 stops10h 27mDelta
Deal found 9/10$243
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/229:45 pmYEG - MDW
2 stops25h 01mMultiple Airlines
Sat 11/11:37 pmMDW - YEG
1 stop24h 34mMultiple Airlines
Deal found 9/9$248
This Delta deal was found by Cheapflights users on 9/11. 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 10/16:40 amYYC - MDW
1 stop9h 55mDelta
Tue 11/49:35 amMDW - YYC
2 stops12h 12mDelta
Deal found 9/11$254
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1412:30 amYYC - MDW
1 stop12h 08mMultiple Airlines
Fri 11/146:15 amMDW - YYC
2 stops12h 15mMultiple Airlines
Deal found 9/9$255
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Tue 9/307:00 amYYC - MDW
2 stops31h 58mMultiple Airlines
Tue 10/78:05 amMDW - YYC
1 stop12h 55mMultiple Airlines
Deal found 9/10$262

Cheapflights Fare Finder

 
Customize your flight search to find flights from Alberta to Midway 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 September 11, 2025.
Use the filters below to find and compare flights from Alberta to Chicago Midway Airport that are best for you.

Fly from

Alberta

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 10/25

6:45 am-1:08 pm

1 stop5h 23m

Chicago Midway

Sat 11/1

9:20 am-1:54 pm

1 stop5h 34m

$223

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 10/26

6:45 am-1:08 pm

1 stop5h 23m

Chicago Midway

Sat 11/1

10:40 am-11:02 pm

2 stops13h 22m

$223

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 10/29

9:15 am-5:43 pm

1 stop7h 28m

Chicago Midway

Sat 11/1

9:20 am-5:20 pm

2 stops9h 00m

$224

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sat 10/18

9:25 am-5:43 pm

1 stop7h 18m

Chicago Midway

Sat 10/25

9:20 am-3:59 pm

1 stop7h 39m

$243

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 10/22

9:45 pm-11:46 pm

2 stops25h 01m

Chicago Midway

Sat 11/1

1:37 pm-1:11 pm

1 stop24h 34m

$248

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 10/3

9:15 am-6:35 pm

1 stop8h 20m

Chicago Midway

Sun 10/5

9:35 am-6:24 pm

1 stop9h 49m

$254

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 10/7

9:15 am-6:25 pm

1 stop8h 10m

Chicago Midway

Tue 10/14

9:35 am-6:24 pm

1 stop9h 49m

$254

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 10/14

12:30 am-1:38 pm

1 stop12h 08m

Chicago Midway

Fri 11/14

6:15 am-5:30 pm

2 stops12h 15m

$255

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/30

7:00 am-3:58 pm

2 stops31h 58m

Chicago Midway

Tue 10/7

8:05 am-8:00 pm

1 stop12h 55m

$262

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/23

12:30 am-4:57 pm

1 stop15h 27m

Chicago Midway

Fri 10/31

6:20 am-7:09 pm

1 stop13h 49m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 34 results
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Best time to book a flight from Alberta to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Alberta 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 Alberta to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Alberta to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Alberta to Chicago Midway Airport?

    Departing from Alberta to Chicago Midway Airport will take you 5h 23m. The distance from Alberta to Chicago Midway Airport is about 1396 mi.

  • What are the most popular routes from Alberta to Chicago Midway Airport?

    The most popular flight routes from Alberta to Chicago Midway Airport are Calgary - Chicago Midway, Edmonton - Chicago Midway and Grande Prairie - Chicago Midway.

  • Can I find deals for flights from Alberta to Midway that include hotel bookings?

    Yes. In addition to deals on Alberta to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Alberta to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Alberta to Midway.

  • Can I find deals for business class flights from Alberta to Midway?

    Yes. Cheapflights offers flight deals from Alberta to Midway 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 Alberta to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Alberta to Chicago Midway Airport (average of $160). Flying from Alberta to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Alberta to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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