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Cheap flights from Alberta to Chicago Midway Airport from C$ 214

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 28/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
5 Jun — 12 Jun1
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 6 May 2026.

Thu 24/127:45 a.m.
YYC
-
MDW
2 stops13h 00m
Delta
Thu 31/1211:20 a.m.
MDW
-
YYC
2 stops12h 53m
Delta
Deal found 2/5C$ 411
Thu 24/127:45 a.m.
YYC
-
MDW
2 stops13h 00m
Delta
Sat 2/111:20 a.m.
MDW
-
YYC
2 stops12h 53m
Delta
Deal found 2/5C$ 444
Fri 29/56:45 a.m.
YYC
-
MDW
1 stop10h 11m
Delta
Tue 9/69:17 a.m.
MDW
-
YYC
2 stops12h 21m
Delta
Deal found 5/5C$ 453
Tue 2/66:45 a.m.
YYC
-
MDW
1 stop10h 11m
Delta
Tue 9/69:17 a.m.
MDW
-
YYC
2 stops12h 21m
Delta
Deal found 5/5C$ 478
Tue 26/56:45 a.m.
YYC
-
MDW
1 stop10h 11m
Delta
Thu 28/59:22 a.m.
MDW
-
YYC
2 stops12h 08m
Delta
Deal found 5/5C$ 485
Thu 7/56:45 a.m.
YYC
-
MDW
2 stops13h 24m
Delta
Sat 16/59:23 a.m.
MDW
-
YYC
2 stops14h 34m
Delta
Deal found 5/5C$ 487
Wed 20/57:00 a.m.
YEG
-
MDW
2 stops10h 33m
Delta
Wed 27/59:22 a.m.
MDW
-
YEG
2 stops11h 18m
Delta
Deal found 5/5C$ 589
Tue 19/57:00 a.m.
YEG
-
MDW
2 stops10h 33m
Delta
Wed 27/59:22 a.m.
MDW
-
YEG
2 stops11h 18m
Delta
Deal found 5/5C$ 600
Thu 28/57:15 a.m.
YEG
-
MDW
3 stops25h 30m
Porter Airlines
Tue 2/610:15 a.m.
MDW
-
YEG
2 stops12h 20m
Porter Airlines
Deal found 2/5C$ 632
Tue 2/611:50 a.m.
YEG
-
MDW
2 stops20h 45m
Porter Airlines
Tue 9/610:15 a.m.
MDW
-
YEG
2 stops12h 20m
Porter Airlines
Deal found 3/5C$ 660
Thu 11/64:55 p.m.
YEG
-
MDW
1 stop15h 40m
Multiple Airlines
Mon 15/610:15 a.m.
MDW
-
YEG
2 stops12h 20m
Multiple Airlines
Deal found 5/5C$ 672
Tue 2/611:50 a.m.
YEG
-
MDW
2 stops20h 45m
Multiple Airlines
Tue 9/610:15 a.m.
MDW
-
YEG
2 stops12h 20m
Multiple Airlines
Deal found 3/5C$ 701

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 6 May 2026.

Round-trip from

C$ 453

One-way from

C$ 214

Popular in

July

Cheapest in

November

Average price

C$ 357
Delta
  • Delta
  • 29/5-9/6
  • 4 total stops
  • 25h 45m total
  • Alberta to Chicago
Search Deals
Delta
  • Delta
  • 28/5
  • 1 total stop
  • 5h 34m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 6 May 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

Tue 26/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Thu 28/5

9:22 a.m.-8:30 p.m.

2 stops12h 08m

C$ 485

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 2/6

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Tue 9/6

1:49 p.m.-8:38 p.m.

1 stop7h 49m

C$ 498

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 22/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Thu 28/5

9:22 a.m.-8:30 p.m.

2 stops12h 08m

C$ 514

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 25/5

6:45 a.m.-1:19 p.m.

1 stop5h 34m

Chicago Midway

Wed 27/5

9:22 a.m.-8:30 p.m.

2 stops12h 08m

C$ 514

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 22/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Tue 26/5

9:22 a.m.-8:30 p.m.

2 stops12h 08m

C$ 514

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 22/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Sun 24/5

9:22 a.m.-8:30 p.m.

2 stops12h 08m

C$ 603

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 11/9

11:40 a.m.-9:46 p.m.

1 stop9h 06m

Chicago Midway

Mon 14/9

1:00 p.m.-8:05 p.m.

1 stop8h 05m

C$ 715

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/6

12:30 a.m.-11:09 a.m.

1 stop9h 39m

Chicago Midway

Mon 15/6

6:00 a.m.-5:10 p.m.

1 stop12h 10m

C$ 736

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 12/7

12:50 a.m.-2:35 p.m.

1 stop12h 45m

Chicago Midway

Mon 20/7

6:00 a.m.-9:50 p.m.

1 stop16h 50m

C$ 744

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Thu 28/5

11:50 a.m.-9:45 a.m.

2 stops20h 55m

Chicago Midway

Tue 2/6

10:15 a.m.-9:35 p.m.

2 stops12h 20m

C$ 747

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/5

Showing 1-10 of 35 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 and Porter Airlines can get you from Alberta to Chicago Midway Airport in just under 10h 11m. Your travel time can differ by up to 10h 44m. The distance from Alberta to Chicago Midway Airport is about 2247 km. Both multi-stop and direct flights can be found to your destination and back.

  • 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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How does Cheapflights help users find flights from Alberta to Midway?

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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