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Cheap flights from Alberta to Chicago Midway Airport from C$ 192

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
4 Aug — 11 Aug1
1 adult

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 30 July 2025.

Round-trip from

C$ 337

One-way from

C$ 192

Popular in

December

Cheapest in

April

Average price

C$ 501
Delta
  • Delta
  • 10/9-13/9
  • 3 total stops
  • 20h 05m total
  • Alberta to Chicago
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Delta
  • Delta
  • 10/9
  • 1 total stop
  • 5h 23m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 164 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 30 July 2025.

Wed 1/106:00 a.m.YEG - MDW
2 stops11h 35mDelta
Wed 15/109:20 a.m.MDW - YEG
1 stop7h 39mDelta
Deal found 30/7C$ 337
Mon 8/96:40 a.m.YYC - MDW
1 stop9h 57mDelta
Sat 25/103:00 p.m.MDW - YYC
1 stop6h 47mDelta
Deal found 28/7C$ 448
Wed 17/912:05 a.m.YEG - MDW
1 stop15h 19mMultiple Airlines
Mon 22/99:35 a.m.MDW - YEG
1 stop12h 45mMultiple Airlines
Deal found 29/7C$ 458
Sat 6/910:00 a.m.YYC - MDW
1 stop12h 17mMultiple Airlines
Mon 8/96:20 a.m.MDW - YYC
1 stop14h 40mMultiple Airlines
Deal found 29/7C$ 468
Thu 18/94:40 p.m.YEG - MDW
1 stop14h 59mPorter Airlines
Mon 22/99:35 a.m.MDW - YEG
1 stop12h 47mPorter Airlines
Deal found 29/7C$ 513
Sat 13/99:25 a.m.YEG - MDW
1 stop7h 10mWestJet
Sat 27/911:00 a.m.MDW - YEG
2 stops11h 20mWestJet
Deal found 30/7C$ 732
Mon 25/811:55 p.m.YYC - MDW
2 stops15h 29mPorter Airlines
Mon 1/95:20 p.m.MDW - YYC
2 stops19h 15mPorter Airlines
Deal found 28/7C$ 757
Sat 6/97:00 a.m.YYC - MDW
2 stops13h 12mWestJet
Mon 8/910:31 a.m.MDW - YYC
2 stops11h 21mWestJet
Deal found 29/7C$ 839
Fri 12/98:50 p.m.YQU - MDW
2 stops11h 57mWestJet
Fri 19/99:20 a.m.MDW - YQU
2 stops10h 33mWestJet
Deal found 29/7C$ 968

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 30 July 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

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 1/10

6:00 a.m.-6:35 p.m.

2 stops11h 35m

Chicago Midway

Wed 15/10

9:20 a.m.-3:59 p.m.

1 stop7h 39m

C$ 337

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 8/9

6:40 a.m.-5:37 p.m.

1 stop9h 57m

Chicago Midway

Sat 25/10

3:00 p.m.-8:47 p.m.

1 stop6h 47m

C$ 448

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 17/9

12:05 a.m.-4:24 p.m.

1 stop15h 19m

Chicago Midway

Mon 22/9

9:35 a.m.-9:20 p.m.

1 stop12h 45m

C$ 458

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 6/9

10:00 a.m.-11:17 p.m.

1 stop12h 17m

Chicago Midway

Mon 8/9

6:20 a.m.-8:00 p.m.

1 stop14h 40m

C$ 468

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Thu 18/9

4:40 p.m.-8:39 a.m.

1 stop14h 59m

Chicago Midway

Mon 22/9

9:35 a.m.-9:22 p.m.

1 stop12h 47m

C$ 513

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sat 13/9

9:25 a.m.-5:35 p.m.

1 stop7h 10m

Chicago Midway

Sat 27/9

11:00 a.m.-9:20 p.m.

2 stops11h 20m

C$ 732

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 25/8

11:55 p.m.-4:24 p.m.

2 stops15h 29m

Chicago Midway

Mon 1/9

5:20 p.m.-11:35 a.m.

2 stops19h 15m

C$ 757

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 6/9

7:00 a.m.-9:12 p.m.

2 stops13h 12m

Chicago Midway

Mon 8/9

10:31 a.m.-8:52 p.m.

2 stops11h 21m

C$ 839

Grande PrairieChicago

YQU - MDW

YQUMDW

Grande Prairie

Fri 12/9

8:50 p.m.-9:47 a.m.

2 stops11h 57m

Chicago Midway

Fri 19/9

9:20 a.m.-6:53 p.m.

2 stops10h 33m

C$ 968

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 10/9

6:40 a.m.-1:03 p.m.

1 stop5h 23m

C$ 192

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

Showing 1-10 of 19 results
1
2

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 30 July 2025.
Read through reviews of airlines operating flights from Alberta to Chicago Midway Airport, such as Porter Airlines,Delta, andWestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,980 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,975 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • What are the cheapest airlines to fly from Alberta to Chicago Midway Airport one-way?

    C$ 192 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Porter Airlines and WestJet, with prices starting from C$ 280 and C$ 399, respectively.

  • 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.

  • What is the cheapest month to book a flight from Alberta to Chicago Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Alberta to Chicago Midway Airport (average of C$ 233). Flying from Alberta to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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

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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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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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