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Cheap flights from Alberta to Chicago Midway Airport from C$ 309

YYC — MDW
4 Dec — 11 Dec1
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

Sat 19/125:10 p.m. -
2 stops26h 20m
Wed 23/128:35 p.m. -
2 stops26h 07m
Deal found 3/11C$ 714
Mon 7/129:15 a.m. -
1 stop7h 35m
Mon 14/1210:24 a.m. -
1 stop5h 36m
Deal found 2/11C$ 725
Thu 3/129:20 p.m. -
2 stops18h 47m
Sun 6/125:02 p.m. -
2 stops22h 13m
Deal found 2/11C$ 726
Mon 7/125:00 p.m. -
2 stops18h 33m
Mon 14/125:02 p.m. -
2 stops22h 13m
Deal found 2/11C$ 754
Mon 23/116:00 a.m. -
2 stops10h 39m
Mon 30/115:29 p.m. -
2 stops21h 01m
Deal found 31/10C$ 761
Mon 23/116:00 a.m. -
2 stops10h 39m
Tue 1/125:30 p.m. -
2 stops21h 00m
Deal found 1/11C$ 774
Thu 3/129:20 p.m. -
2 stops18h 47m
Thu 10/125:02 p.m. -
2 stops22h 13m
Deal found 2/11C$ 775
Wed 18/119:20 p.m. -
2 stops20h 27m
Wed 25/118:42 p.m. -
2 stops19h 18m
Deal found 2/11C$ 783
Tue 24/1112:55 a.m. -
2 stops34h 30m
Mon 30/1110:34 a.m. -
2 stops27h 56m
Deal found 1/11C$ 785

Find flight deals from Alberta to Midway

Round-trip from

C$ 714

One-way from

C$ 309

Popular in

December

Cheapest in

April

Average price

C$ 479
19/12-23/12
  • 19/12-23/12
  • 4 total stops
  • 52h 27m total
  • Alberta to Chicago
Search Deals
30/11-31/12
  • 30/11-31/12
  • 3 total stops
  • 40h 56m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2026
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Cheapflights Fare Finder

 
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

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Thu 17/12

7:00 a.m.-7:30 p.m.

2 stops36h 30m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 359

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Wed 20/1

6:00 a.m.-11:46 p.m.

2 stops17h 46m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 367

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Mon 16/11

7:30 a.m.-11:22 a.m.

2 stops27h 52m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 378

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Thu 3/12

4:50 p.m.-9:45 a.m.

3 stops40h 55m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 383

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Wed 16/12

5:00 p.m.-12:03 p.m.

2 stops43h 03m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 383

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Sun 13/12

6:00 a.m.-9:45 a.m.

3 stops27h 45m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 387
Quickest round-trip

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Sun 13/12

9:15 a.m.-4:50 p.m.

1 stop7h 35m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 402

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Wed 2/12

7:30 a.m.-2:41 p.m.

2 stops31h 11m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 404

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Mon 23/11

12:55 a.m.-12:51 p.m.

2 stops11h 56m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 413

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Wed 2/12

12:55 a.m.-1:01 p.m.

2 stops12h 06m

Chicago Midway

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 413

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 20 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

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

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

    Delta and WestJet can get you from Alberta to Chicago Midway Airport in just under 7h 35m. Your travel time can differ by up to 3h 04m. The distance from Alberta to Chicago Midway Airport is about 2303 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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