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Cheap flights from Calgary to Chicago Midway Airport from C$ 271

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 25/12. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
22 Aug — 29 Aug1
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 23 July 2026.

Mon 23/117:45 a.m.
YYC
-
MDW
2 stops13h 25m
Delta
Thu 26/1110:35 a.m.
MDW
-
YYC
2 stops13h 38m
Delta
Deal found 20/7C$ 376
Thu 10/127:45 a.m.
YYC
-
MDW
1 stop8h 05m
Delta
Thu 17/1212:30 p.m.
MDW
-
YYC
2 stops11h 43m
Delta
Deal found 20/7C$ 438
Sat 25/76:45 a.m.
YYC
-
MDW
1 stop10h 07m
Delta
Tue 18/89:59 a.m.
MDW
-
YYC
2 stops14h 05m
Delta
Deal found 19/7C$ 443
Thu 29/1012:30 a.m.
YYC
-
MDW
2 stops11h 18m
Delta
Mon 2/119:59 a.m.
MDW
-
YYC
2 stops10h 16m
Delta
Deal found 23/7C$ 472
Sat 25/76:45 a.m.
YYC
-
MDW
1 stop10h 07m
Delta
Wed 2/99:24 a.m.
MDW
-
YYC
2 stops12h 11m
Delta
Deal found 19/7C$ 507
Thu 17/127:45 a.m.
YYC
-
MDW
2 stops13h 25m
Delta
Fri 25/1211:20 a.m.
MDW
-
YYC
2 stops12h 53m
Delta
Deal found 19/7C$ 520

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 23 July 2026.

Round-trip from

C$ 376

One-way from

C$ 271

Popular in

June

Cheapest in

November

Average price

C$ 403
Delta
  • Delta
  • 23/11-26/11
  • 4 total stops
  • 27h 03m total
  • Calgary to Chicago
Search Deals
Delta
  • Delta
  • 25/12
  • 2 total stops
  • 7h 37m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 23 July 2026.
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 - MDW

YYCMDW

Calgary

Mon 23/11

7:45 a.m.-9:10 p.m.

2 stops13h 25m

Chicago Midway

Thu 26/11

10:35 a.m.-12:13 a.m.

2 stops13h 38m

C$ 376

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

12:30 a.m.-12:05 p.m.

1 stop10h 35m

Chicago Midway

Mon 2/11

12:28 p.m.-9:30 p.m.

1 stop9h 02m

C$ 537

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 12/11

7:45 a.m.-3:50 p.m.

1 stop8h 05m

Chicago Midway

Sun 15/11

12:30 p.m.-9:54 p.m.

1 stop9h 24m

C$ 543
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 14/10

11:00 a.m.-6:05 p.m.

1 stop6h 05m

Chicago Midway

Sat 17/10

9:59 a.m.-7:40 p.m.

2 stops10h 41m

C$ 603

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 24/12

7:45 a.m.-3:50 p.m.

1 stop8h 05m

Chicago Midway

Thu 31/12

11:20 a.m.-12:13 a.m.

2 stops12h 53m

C$ 623

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 24/9

12:20 a.m.-10:58 a.m.

1 stop9h 38m

Chicago Midway

Sun 27/9

7:25 a.m.-5:10 p.m.

1 stop10h 45m

C$ 643
Cheapest one-way

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 25/12

7:45 a.m.-3:22 p.m.

2 stops7h 37m

C$ 271

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 25/11

7:45 a.m.-3:50 p.m.

1 stop8h 05m

C$ 275

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 4/10

12:20 a.m.-11:54 a.m.

1 stop10h 34m

C$ 286

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/10

12:20 a.m.-9:52 a.m.

1 stop8h 32m

C$ 286

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/7

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

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 13h 25m. 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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