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Midway

$139+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap 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 December 16, 2025.

This Delta deal was found by Cheapflights users on 12/15. 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.
Thu 12/186:35 amYYC - MDW
2 stops16h 12mDelta
Wed 1/79:50 amMDW - YYC
2 stops10h 25mDelta
Deal found 12/15$376
This Delta deal was found by Cheapflights users on 12/15. 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.
Thu 12/186:35 amYYC - MDW
2 stops16h 12mDelta
Tue 1/69:50 amMDW - YYC
2 stops14h 12mDelta
Deal found 12/15$394
This Delta deal was found by Cheapflights users on 12/15. 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.
Thu 12/186:35 amYYC - MDW
2 stops16h 12mDelta
Mon 1/59:50 amMDW - YYC
2 stops14h 12mDelta
Deal found 12/15$435
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Wed 12/318:55 amYYC - MDW
1 stop12h 17mMultiple Airlines
Thu 1/812:50 pmMDW - YYC
1 stop11h 02mMultiple Airlines
Deal found 12/14$558
This FlightHub deal was found by Cheapflights users on 12/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:00 pmYYC - MDW
2 stops16h 05mWestJet
Thu 1/81:28 pmMDW - YYC
2 stops12h 16mWestJet
Deal found 12/14$622
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:15 amYEG - MDW
1 stop7h 04mWestJet
Tue 12/305:59 pmMDW - YEG
1 stop23h 00mWestJet
Deal found 12/15$655
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:35 amYYC - MDW
1 stop5h 35mMultiple Airlines
Tue 1/62:03 pmMDW - YYC
1 stop9h 49mMultiple Airlines
Deal found 12/15$682
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:35 amYYC - MDW
1 stop5h 35mWestJet
Tue 1/61:28 pmMDW - YYC
2 stops20h 38mWestJet
Deal found 12/15$699
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:15 amYEG - MDW
1 stop7h 04mWestJet
Mon 12/299:29 amMDW - YEG
2 stops12h 31mWestJet
Deal found 12/15$703
This Justfly.com deal was found by Cheapflights users on 12/14. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:40 pmYYC - MDW
2 stops34h 26mWestJet
Fri 1/91:28 pmMDW - YYC
2 stops12h 16mWestJet
Deal found 12/14$704
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:15 amYEG - MDW
1 stop7h 04mMultiple Airlines
Mon 12/294:15 pmMDW - YEG
1 stop25h 35mMultiple Airlines
Deal found 12/15$783
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:00 amYEG - MDW
2 stops25h 05mPorter Airlines
Tue 12/3011:00 amMDW - YEG
2 stops11h 59mPorter Airlines
Deal found 12/15$1,266

Find flight deals from Alberta to Midway

Keep the following information in mind while searching for Alberta to Midway flight deals. Data was last updated December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$224
(Delta)

One-way from

$139
(Delta)

Popular in

July

Cheapest in

April

Average price

$291
Provider with most accurate pricing for Calgary-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Calgary-Chicago (CHI) flights.
Search Deals
From Alberta to Chicago Midway
Search Deals
One-way flight from Alberta to Chicago Midway
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 16, 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

Wed 1/14

6:30 am-1:09 pm

1 stop5h 39m

Chicago Midway

Sun 1/18

9:50 am-11:02 pm

2 stops14h 12m

$224

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 1/30

6:30 am-1:09 pm

1 stop5h 39m

Chicago Midway

Fri 2/6

1:51 pm-8:54 pm

1 stop8h 03m

$244

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sat 1/31

5:00 pm-3:58 pm

1 stop21h 58m

Chicago Midway

Sat 2/7

9:38 am-10:47 pm

2 stops14h 09m

$257

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 4/14

12:30 am-11:56 am

1 stop10h 26m

Chicago Midway

Wed 4/22

9:20 am-7:12 pm

2 stops10h 52m

$270

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/26

9:15 am-6:31 pm

1 stop8h 16m

Chicago Midway

Sat 5/30

9:30 am-6:25 pm

1 stop9h 55m

$270

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 4/24

12:45 am-9:51 am

1 stop8h 06m

Chicago Midway

Mon 4/27

1:05 pm-7:50 pm

1 stop7h 45m

$272

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sat 4/11

12:45 am-9:55 am

1 stop8h 10m

Chicago Midway

Tue 4/14

9:20 am-3:55 pm

1 stop7h 35m

$272

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 1/28

12:45 am-11:45 am

1 stop10h 00m

Chicago Midway

Thu 2/5

5:01 pm-10:47 pm

2 stops30h 46m

$285

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 1/28

6:30 am-1:09 pm

1 stop5h 39m

Chicago Midway

Wed 2/4

9:32 am-8:54 pm

2 stops12h 22m

$290

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sun 2/15

9:55 pm-11:54 pm

2 stops24h 59m

Chicago Midway

Fri 2/20

7:53 pm-12:13 pm

1 stop17h 20m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 27 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 39m. 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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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