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Cheap flights from Calgary to Chicago Midway Airport from C$ 219

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
25 Feb — 4 Mar1
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
Explore the most affordable flight options available from Calgary to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 26 January 2026.

Wed 25/26:30 a.m.
YYC
-
MDW
1 stop5h 35m
Delta
Tue 3/39:34 a.m.
MDW
-
YYC
2 stops12h 20m
Delta
Deal found 25/1C$ 316
Wed 11/36:30 a.m.
YYC
-
MDW
1 stop5h 55m
Delta
Wed 18/39:30 a.m.
MDW
-
YYC
2 stops10h 42m
Delta
Deal found 25/1C$ 414
Tue 24/26:30 a.m.
YYC
-
MDW
1 stop5h 35m
Delta
Mon 2/39:50 a.m.
MDW
-
YYC
2 stops14h 15m
Delta
Deal found 25/1C$ 416
Wed 4/26:30 a.m.
YYC
-
MDW
1 stop5h 36m
Delta
Wed 11/29:33 a.m.
MDW
-
YYC
2 stops12h 21m
Delta
Deal found 25/1C$ 418
Thu 26/26:30 a.m.
YYC
-
MDW
1 stop5h 35m
Delta
Thu 5/39:34 a.m.
MDW
-
YYC
2 stops12h 24m
Delta
Deal found 25/1C$ 427
Tue 24/26:30 a.m.
YYC
-
MDW
1 stop5h 35m
Delta
Sun 8/39:35 a.m.
MDW
-
YYC
2 stops10h 53m
Delta
Deal found 25/1C$ 429
Fri 20/26:30 a.m.
YYC
-
MDW
2 stops12h 30m
Multiple Airlines
Mon 23/211:05 a.m.
MDW
-
YYC
1 stop14h 00m
Multiple Airlines
Deal found 25/1C$ 441
Thu 5/36:30 a.m.
YYC
-
MDW
1 stop5h 35m
Delta
Sun 8/39:35 a.m.
MDW
-
YYC
2 stops12h 23m
Delta
Deal found 25/1C$ 445
Fri 20/26:30 a.m.
YYC
-
MDW
2 stops10h 07m
Delta
Mon 23/29:50 a.m.
MDW
-
YYC
2 stops10h 22m
Delta
Deal found 25/1C$ 448
Thu 5/312:30 a.m.
YYC
-
MDW
1 stop8h 24m
Delta
Sun 8/39:35 a.m.
MDW
-
YYC
2 stops12h 23m
Delta
Deal found 24/1C$ 453
Sat 28/212:15 a.m.
YYC
-
MDW
2 stops11h 31m
Delta
Wed 4/39:50 a.m.
MDW
-
YYC
2 stops10h 22m
Delta
Deal found 25/1C$ 455

Find flight deals from Calgary to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 26 January 2026.

Round-trip from

C$ 316

One-way from

C$ 219

Popular in

July

Cheapest in

April

Average price

C$ 320
Delta
  • Delta
  • 25/2-4/3
  • 3 total stops
  • 16h 11m total
  • Calgary to Chicago
Search Deals
Delta
  • Delta
  • 10/2
  • 1 total stop
  • 5h 36m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 62 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 January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary 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 26 January 2026.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Calgary

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 27/2

6:30 a.m.-5:37 p.m.

2 stops10h 07m

Chicago Midway

Tue 3/3

1:49 p.m.-8:54 p.m.

1 stop8h 05m

C$ 316

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/3

6:30 a.m.-1:25 p.m.

1 stop5h 55m

Chicago Midway

Wed 18/3

9:30 a.m.-7:12 p.m.

2 stops10h 42m

C$ 414

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/2

6:30 a.m.-1:05 p.m.

1 stop5h 35m

Chicago Midway

Wed 4/3

10:49 a.m.-7:09 p.m.

1 stop9h 20m

C$ 416

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 24/2

6:30 a.m.-5:37 p.m.

2 stops10h 07m

Chicago Midway

Mon 2/3

9:50 a.m.-7:12 p.m.

2 stops10h 22m

C$ 416

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/2

6:30 a.m.-1:05 p.m.

1 stop5h 35m

Chicago Midway

Mon 2/3

9:50 a.m.-11:05 p.m.

2 stops14h 15m

C$ 416

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 7/2

6:30 a.m.-4:16 p.m.

1 stop8h 46m

Chicago Midway

Tue 10/2

1:51 p.m.-8:54 p.m.

1 stop8h 03m

C$ 418

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 6/2

6:30 a.m.-1:06 p.m.

1 stop5h 36m

Chicago Midway

Mon 9/2

9:53 a.m.-11:02 p.m.

2 stops14h 09m

C$ 418

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 7/2

6:30 a.m.-4:16 p.m.

1 stop8h 46m

Chicago Midway

Mon 9/2

9:53 a.m.-11:02 p.m.

2 stops14h 09m

C$ 418

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 6/2

6:30 a.m.-1:06 p.m.

1 stop5h 36m

Chicago Midway

Tue 10/2

1:51 p.m.-8:54 p.m.

1 stop8h 03m

C$ 418

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 6/2

6:30 a.m.-1:06 p.m.

1 stop5h 36m

Chicago Midway

Wed 11/2

9:33 a.m.-8:54 p.m.

2 stops12h 21m

C$ 418

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/1

Showing 1-10 of 21 results
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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
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.

Related info for your journey

Find useful and relevant information for your journey from Calgary to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 10h 07m. 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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