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Cheap flights from Alberta to Chicago Midway Airport from C$ 248

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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
20 Jul — 27 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Alberta to Midway

Enter your travel dates to find the best prices.

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 20 June 2026.

Tue 1/96:45 a.m.
YYC
-
MDW
1 stop5h 25m
Delta
Sun 6/99:24 a.m.
MDW
-
YYC
2 stops12h 11m
Delta
Deal found 19/6C$ 415
Wed 21/107:45 a.m.
YYC
-
MDW
2 stops13h 25m
Delta
Sat 24/1012:30 p.m.
MDW
-
YYC
2 stops11h 43m
Delta
Deal found 17/6C$ 416
Wed 23/96:45 a.m.
YYC
-
MDW
1 stop5h 22m
Delta
Sat 10/1010:35 a.m.
MDW
-
YYC
2 stops13h 38m
Delta
Deal found 15/6C$ 436
Fri 30/107:45 a.m.
YYC
-
MDW
1 stop8h 05m
Delta
Mon 2/1112:30 p.m.
MDW
-
YYC
1 stop9h 24m
Delta
Deal found 19/6C$ 457
Wed 23/96:45 a.m.
YYC
-
MDW
1 stop5h 22m
Delta
Sun 11/109:30 a.m.
MDW
-
YYC
2 stops12h 24m
Delta
Deal found 15/6C$ 502
Sun 4/1012:20 a.m.
YYC
-
MDW
1 stop10h 35m
Delta
Tue 6/1012:30 p.m.
MDW
-
YYC
1 stop9h 24m
Delta
Deal found 19/6C$ 505
Mon 28/97:00 a.m.
YYC
-
MDW
1 stop8h 11m
Delta
Tue 6/1012:30 p.m.
MDW
-
YYC
1 stop9h 24m
Delta
Deal found 17/6C$ 508
Mon 16/119:15 a.m.
YEG
-
MDW
2 stops11h 55m
Delta
Mon 30/119:55 a.m.
MDW
-
YEG
1 stop8h 00m
Delta
Deal found 20/6C$ 582
Fri 25/99:40 a.m.
YEG
-
MDW
1 stop7h 31m
Delta
Tue 29/99:30 a.m.
MDW
-
YEG
2 stops8h 25m
Delta
Deal found 19/6C$ 610
Thu 10/99:40 a.m.
YEG
-
MDW
1 stop7h 39m
Delta
Sun 13/99:20 a.m.
MDW
-
YEG
1 stop8h 35m
Delta
Deal found 18/6C$ 614
Wed 26/89:40 a.m.
YEG
-
MDW
1 stop7h 21m
Delta
Wed 16/99:49 a.m.
MDW
-
YEG
1 stop8h 06m
Delta
Deal found 18/6C$ 627
Thu 27/89:40 a.m.
YEG
-
MDW
1 stop7h 21m
Delta
Tue 1/99:59 a.m.
MDW
-
YEG
1 stop7h 56m
Delta
Deal found 19/6C$ 637

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 20 June 2026.

Round-trip from

C$ 415

One-way from

C$ 248

Popular in

June

Cheapest in

November

Average price

C$ 548
Delta
  • Delta
  • 1/9-6/9
  • 3 total stops
  • 17h 36m total
  • Alberta to Chicago
Search Deals
Delta
  • Delta
  • 10/9
  • 1 total stop
  • 5h 45m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 123 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 629,999 searches. Data last updated 20 June 2026.
Use the filters below to find and compare flights from Alberta to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 21/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Sat 24/10

12:30 p.m.-11:13 p.m.

2 stops11h 43m

C$ 416

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 30/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Mon 2/11

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 419

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 27/11

7:45 a.m.-10:10 p.m.

2 stops13h 25m

Chicago Midway

Wed 2/12

12:30 p.m.-11:13 p.m.

2 stops11h 43m

C$ 461

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 13/11

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Tue 17/11

10:35 a.m.-11:13 p.m.

2 stops13h 38m

C$ 461

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 25/9

9:40 a.m.-6:11 p.m.

1 stop7h 31m

Chicago Midway

Tue 29/9

9:49 a.m.-4:55 p.m.

1 stop8h 06m

C$ 610
Quickest round-trip

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sun 13/9

9:40 a.m.-6:05 p.m.

1 stop7h 25m

Chicago Midway

Wed 16/9

9:49 a.m.-4:55 p.m.

1 stop8h 06m

C$ 614

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sun 13/9

9:40 a.m.-6:05 p.m.

1 stop7h 25m

Chicago Midway

Tue 15/9

9:30 a.m.-4:55 p.m.

2 stops8h 25m

C$ 614

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Thu 10/9

9:40 a.m.-6:19 p.m.

1 stop7h 39m

Chicago Midway

Tue 15/9

9:30 a.m.-4:55 p.m.

2 stops8h 25m

C$ 614

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Thu 27/8

7:30 a.m.-6:33 p.m.

2 stops10h 03m

Chicago Midway

Tue 1/9

9:24 a.m.-4:55 p.m.

2 stops8h 31m

C$ 637

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Thu 13/8

9:40 a.m.-6:01 p.m.

1 stop7h 21m

Chicago Midway

Thu 20/8

1:27 p.m.-12:44 a.m.

2 stops12h 17m

C$ 643

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/6

Showing 1-10 of 31 resultsSorted by cheapest first
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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?

    Delta can get you from Alberta to Chicago Midway Airport in just under 8h 05m. Your travel time can differ by up to . The distance from Alberta to Chicago Midway Airport is about 2247 km.

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

    Most travellers choose Calgary - Chicago Midway, Edmonton - Chicago Midway or Grande Prairie - Chicago Midway when deciding on the best route from Alberta to Chicago Midway Airport.

  • 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

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Cheapflights makes it easy to find Alberta to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Alberta to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Alberta.

Can Cheapflights find flights from Alberta to Midway with no change fees?

Certainly. Search results for flights to Midway from Alberta shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Alberta to Midway become cheaper?

Yes! Start tracking prices for Alberta to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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