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Cheap flights from Calgary to Chicago Midway Airport from C$ 195

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 17/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
26 May — 2 Jun1
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 April 2026.

Sat 5/96:35 a.m.
YYC
-
MDW
2 stops14h 11m
Delta
Wed 9/96:00 a.m.
MDW
-
YYC
2 stops18h 06m
Delta
Deal found 25/4C$ 348
Sun 26/46:40 a.m.
YYC
-
MDW
2 stops10h 18m
Delta
Wed 29/49:27 a.m.
MDW
-
YYC
2 stops12h 13m
Delta
Deal found 24/4C$ 377
Sat 24/107:45 a.m.
YYC
-
MDW
1 stop8h 05m
Delta
Fri 4/1212:30 p.m.
MDW
-
YYC
1 stop9h 24m
Delta
Deal found 24/4C$ 380
Tue 19/56:45 a.m.
YYC
-
MDW
1 stop10h 11m
Delta
Thu 4/69:23 a.m.
MDW
-
YYC
2 stops14h 34m
Delta
Deal found 22/4C$ 384
Thu 21/511:00 a.m.
YYC
-
MDW
1 stop6h 33m
Delta
Thu 28/51:22 p.m.
MDW
-
YYC
1 stop7h 43m
Delta
Deal found 23/4C$ 395
Thu 21/56:45 a.m.
YYC
-
MDW
1 stop10h 11m
Delta
Thu 4/69:23 a.m.
MDW
-
YYC
2 stops14h 34m
Delta
Deal found 22/4C$ 396
Tue 26/56:45 a.m.
YYC
-
MDW
1 stop5h 34m
Delta
Sun 31/59:23 a.m.
MDW
-
YYC
2 stops14h 34m
Delta
Deal found 21/4C$ 404
Tue 12/56:45 a.m.
YYC
-
MDW
1 stop10h 11m
Delta
Tue 26/56:23 a.m.
MDW
-
YYC
2 stops15h 07m
Delta
Deal found 24/4C$ 425
Thu 28/56:45 a.m.
YYC
-
MDW
1 stop10h 11m
Delta
Sat 30/59:22 a.m.
MDW
-
YYC
2 stops12h 08m
Delta
Deal found 21/4C$ 436
Tue 19/512:30 a.m.
YYC
-
MDW
1 stop9h 39m
Multiple Airlines
Thu 4/66:00 a.m.
MDW
-
YYC
1 stop12h 10m
Multiple Airlines
Deal found 25/4C$ 440
Sat 24/107:45 a.m.
YYC
-
MDW
1 stop8h 05m
Delta
Thu 3/1212:30 p.m.
MDW
-
YYC
1 stop9h 24m
Delta
Deal found 24/4C$ 441
Fri 22/511:00 a.m.
YYC
-
MDW
1 stop6h 33m
Delta
Thu 4/69:23 a.m.
MDW
-
YYC
2 stops11h 17m
Delta
Deal found 22/4C$ 443

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 April 2026.

Round-trip from

C$ 348

One-way from

C$ 195

Popular in

March

Cheapest in

November

Average price

C$ 344
Delta
  • Delta
  • 5/9-9/9
  • 4 total stops
  • 32h 17m total
  • Calgary to Chicago
Search Deals
Delta
  • Delta
  • 17/5
  • 1 total stop
  • 10h 11m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 38 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 April 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 April 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

Sat 5/9

6:35 a.m.-9:46 p.m.

2 stops14h 11m

Chicago Midway

Wed 9/9

6:00 a.m.-11:06 p.m.

2 stops18h 06m

C$ 348

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 26/5

6:45 a.m.-9:09 p.m.

2 stops13h 24m

Chicago Midway

Sat 30/5

6:23 a.m.-8:30 p.m.

2 stops15h 07m

C$ 404

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 27/5

6:45 a.m.-1:19 p.m.

1 stop5h 34m

Chicago Midway

Sat 30/5

6:23 a.m.-8:30 p.m.

2 stops15h 07m

C$ 404
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 26/5

6:45 a.m.-1:19 p.m.

1 stop5h 34m

Chicago Midway

Sun 31/5

9:23 a.m.-10:57 p.m.

2 stops14h 34m

C$ 404

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 12/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Tue 26/5

6:23 a.m.-8:30 p.m.

2 stops15h 07m

C$ 425

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 28/5

6:45 a.m.-9:09 p.m.

2 stops13h 24m

Chicago Midway

Sat 30/5

9:22 a.m.-8:30 p.m.

2 stops12h 08m

C$ 436

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 23/5

6:45 a.m.-9:09 p.m.

2 stops13h 24m

Chicago Midway

Thu 4/6

9:23 a.m.-7:40 p.m.

2 stops11h 17m

C$ 445

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 24/5

7:45 a.m.-5:56 p.m.

2 stops9h 11m

Chicago Midway

Thu 4/6

9:23 a.m.-7:40 p.m.

2 stops11h 17m

C$ 445

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 26/5

6:45 a.m.-9:09 p.m.

2 stops13h 24m

Chicago Midway

Tue 2/6

9:22 a.m.-8:30 p.m.

2 stops12h 08m

C$ 456

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 24/9

7:15 a.m.-9:46 p.m.

2 stops13h 31m

Chicago Midway

Mon 28/9

6:00 a.m.-11:06 p.m.

2 stops18h 06m

C$ 474

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/4

Showing 1-10 of 21 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
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 14h 11m. 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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