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Cheap flights from Alberta to Chicago Midway Airport from C$ 222

YYC — MDW
18 Oct — 25 Oct1
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 31/106:35 a.m. -
2 stops9h 12m
Fri 6/1112:27 p.m. -
2 stops12h 43m
Deal found 15/9C$ 365
Wed 28/106:35 a.m. -
2 stops10h 25m
Wed 4/1112:27 p.m. -
1 stop10h 13m
Deal found 13/9C$ 400
Fri 4/128:45 a.m. -
1 stop7h 05m
Fri 11/1212:39 p.m. -
2 stops12h 42m
Deal found 16/9C$ 407
Sat 14/117:25 a.m. -
2 stops9h 39m
Wed 18/1112:30 p.m. -
2 stops12h 47m
Deal found 14/9C$ 421
Fri 30/107:45 a.m. -
1 stop8h 02m
Mon 2/1112:27 p.m. -
1 stop10h 13m
Deal found 13/9C$ 453
Wed 21/107:00 a.m. -
1 stop15h 43m
Wed 28/106:16 a.m. -
1 stop13h 39m
Deal found 14/9C$ 492
Tue 27/1012:25 a.m. -
1 stop16h 22m
Wed 4/116:16 a.m. -
1 stop13h 39m
Deal found 13/9C$ 506
Thu 29/107:45 a.m. -
2 stops13h 48m
Thu 5/1112:27 p.m. -
1 stop10h 13m
Deal found 14/9C$ 509
Sat 17/109:40 a.m. -
1 stop6h 07m
Wed 21/101:27 p.m. -
2 stops12h 17m
Deal found 17/9C$ 512
Mon 16/119:15 a.m. -
2 stops12h 39m
Mon 30/1110:34 a.m. -
1 stop6h 26m
Deal found 17/9C$ 513
Sat 31/106:00 a.m. -
2 stops10h 47m
Sat 7/117:25 a.m. -
2 stops15h 00m
Deal found 16/9C$ 609
Fri 16/1011:25 p.m. -
1 stop10h 35m
Sat 24/1011:45 a.m. -
1 stop13h 55m
Deal found 15/9C$ 623

Find flight deals from Alberta to Midway

Round-trip from

C$ 365

One-way from

C$ 222

Popular in

June

Cheapest in

January

Average price

C$ 432
Delta
  • Delta
  • 31/10-6/11
  • 4 total stops
  • 21h 55m total
  • Alberta to Chicago
Search Deals
Delta
  • Delta
  • 22/11-31/12
  • 2 total stops
  • 13h 09m total
  • Alberta to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 50 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 September 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

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 30/10

7:45 a.m.-4:47 p.m.

1 stop8h 02m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 222

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 7/10

7:45 a.m.-4:47 p.m.

1 stop8h 02m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 222

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 3/10

6:35 a.m.-6:22 p.m.

2 stops10h 47m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 222

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 21/10

7:45 a.m.-4:47 p.m.

1 stop8h 02m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 229

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 14/1

7:15 a.m.-3:50 p.m.

2 stops8h 35m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 242

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 15/1

8:45 a.m.-3:50 p.m.

1 stop7h 05m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 242

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 17/11

8:45 a.m.-5:04 p.m.

2 stops8h 19m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 243

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 14/11

8:45 a.m.-3:39 p.m.

1 stop6h 54m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 273
Quickest round-trip

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Sat 24/10

9:40 a.m.-4:47 p.m.

1 stop6h 07m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 297

EdmontonChicago

YEG Edmonton - MDW Chicago Midway

YEGMDW

Edmonton

Sat 3/10

9:40 a.m.-5:59 p.m.

1 stop7h 19m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/9

Showing 1-10 of 26 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 can get you from Alberta to Chicago Midway Airport in just under 8h 02m. 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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