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Cheap flights from Calgary to Chicago Midway Airport from C$ 240

YYC — MDW
7 Oct — 14 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Calgary to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Calgary to Midway

Sat 14/117:25 a.m. -
2 stops9h 39m
Wed 18/1112:30 p.m. -
2 stops12h 47m
Deal found 5/9C$ 370
Tue 17/118:45 a.m. -
1 stop6h 54m
Mon 23/1110:34 a.m. -
2 stops14h 43m
Deal found 4/9C$ 372
Fri 30/107:45 a.m. -
1 stop8h 02m
Mon 2/1110:12 a.m. -
2 stops14h 58m
Deal found 3/9C$ 420
Wed 21/107:45 a.m. -
1 stop8h 02m
Wed 28/1012:27 p.m. -
2 stops11h 43m
Deal found 5/9C$ 464
Fri 23/1011:00 a.m. -
1 stop6h 00m
Thu 29/1012:27 p.m. -
1 stop9h 13m
Deal found 3/9C$ 471
Sun 6/96:45 a.m. -
1 stop8h 12m
Sat 12/99:29 a.m. -
2 stops12h 13m
Deal found 5/9C$ 487
Fri 6/111:25 a.m. -
1 stop8h 12m
Tue 10/1112:30 p.m. -
2 stops12h 47m
Deal found 3/9C$ 491
Sat 10/1011:00 a.m. -
1 stop6h 00m
Tue 10/1112:30 p.m. -
2 stops12h 47m
Deal found 4/9C$ 495
Wed 16/95:50 p.m. -
2 stops13h 58m
Tue 20/1010:12 a.m. -
2 stops13h 58m
Deal found 4/9C$ 500

Find flight deals from Calgary to Midway

Round-trip from

C$ 370

One-way from

C$ 240

Popular in

June

Cheapest in

January

Average price

C$ 424
Delta
  • Delta
  • 14/11-18/11
  • 4 total stops
  • 22h 26m total
  • Calgary to Chicago
Search Deals
Delta
  • Delta
  • 11/2-31/12
  • 2 total stops
  • 8h 52m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 16 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 Calgary 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

Thu 11/2

8:45 a.m.-5:37 p.m.

2 stops8h 52m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 240
Quickest round-trip

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 22/9

6:35 a.m.-1:20 p.m.

1 stop5h 45m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 247

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 22/1

8:45 a.m.-9:10 p.m.

2 stops12h 25m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 271

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 12/9

6:35 a.m.-4:57 p.m.

2 stops9h 22m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 278

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 6/11

1:25 a.m.-11:47 a.m.

2 stops10h 22m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 290

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 2/10

12:20 a.m.-10:36 a.m.

1 stop9h 16m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 294

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 17/10

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

1 stop6h 00m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 305

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 14/10

7:00 a.m.-4:14 p.m.

1 stop8h 14m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 305

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Mon 5/10

12:20 a.m.-10:03 a.m.

1 stop8h 43m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 305

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 2/10

11:50 p.m.-12:39 p.m.

2 stops11h 49m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 305

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 22 resultsSorted by cheapest first
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Best time to book a flight from Calgary to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Calgary with our price prediction graph.
Estimated round-trip price

Related info for your journey

  • What airport do you fly from for flights from Calgary to Chicago Midway?

    Calgary (YYC), located 9.3 km from the city centre, is the airport you fly out of when you book flights from Calgary to Chicago Midway. 0 airlines have flights from Calgary to Chicago Midway on a regular basis. Booking flights from Calgary to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

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

    There are many flights that can get you from Calgary to Chicago Midway Airport in 9h 39m. Fly via Delta to get the fastest option. There are 2247 km between Calgary and Chicago Midway Airport.

  • Can I find deals for flights from Calgary to Midway that include hotel bookings?

    Yes. In addition to deals on Calgary to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Midway.

  • Can I find deals for business class flights from Calgary to Midway?

    Yes. Cheapflights offers flight deals from Calgary 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 Calgary to Midway?

Deals for Calgary to Midway flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Calgary 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 Calgary.

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

Yes, we can. To see specific flights from Calgary to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes, Cheapflights offers price alerts on Calgary to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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