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Cheap flights from Calgary to Chicago Midway Airport from C$ 283

YYC — MDW
24 Nov — 1 Dec1
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 5/127:25 a.m. -
2 stops9h 25m
Sat 12/1212:39 p.m. -
1 stop9h 28m
Deal found 21/10C$ 485
Fri 30/107:45 a.m. -
2 stops13h 48m
Mon 2/1110:12 a.m. -
2 stops13h 58m
Deal found 22/10C$ 506
Wed 9/128:45 a.m. -
1 stop8h 05m
Sat 12/1212:39 p.m. -
1 stop9h 28m
Deal found 20/10C$ 515
Thu 22/107:45 a.m. -
1 stop8h 02m
Wed 28/1010:12 a.m. -
2 stops13h 58m
Deal found 21/10C$ 517
Sat 21/118:45 a.m. -
1 stop7h 54m
Sat 28/1112:30 p.m. -
1 stop9h 28m
Deal found 24/10C$ 534
Wed 9/128:45 a.m. -
2 stops9h 16m
Mon 14/1210:24 a.m. -
2 stops13h 57m
Deal found 20/10C$ 541
Wed 9/128:45 a.m. -
1 stop8h 05m
Wed 16/1212:39 p.m. -
2 stops11h 42m
Deal found 20/10C$ 583
Tue 27/107:45 a.m. -
2 stops13h 48m
Tue 3/1110:12 a.m. -
2 stops13h 58m
Deal found 22/10C$ 584
Sat 24/106:35 a.m. -
2 stops14h 58m
Tue 27/1012:27 p.m. -
1 stop9h 13m
Deal found 22/10C$ 585
Wed 21/107:45 a.m. -
2 stops13h 48m
Sat 24/1012:27 p.m. -
2 stops11h 45m
Deal found 20/10C$ 594

Find flight deals from Calgary to Midway

Round-trip from

C$ 485

One-way from

C$ 283

Popular in

March

Cheapest in

April

Average price

C$ 410
Delta
  • Delta
  • 5/12-12/12
  • 3 total stops
  • 18h 53m total
  • Calgary to Chicago
Search Deals
Delta
  • Delta
  • 12/12-31/12
  • 1 total stop
  • 8h 05m total
  • Calgary to Chicago
Search Deals
High demand for flights, 8% potential price rise
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Cheapest flight prices on average. 1% potential price decrease (C$ 12 potential savings vs. average RT price).
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Average for round-trip flights in October 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

Wed 4/11

7:25 a.m.-6:00 p.m.

2 stops10h 35m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 283

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 3/11

8:45 a.m.-10:33 p.m.

2 stops13h 48m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 293
Quickest round-trip

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 5/12

8:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 297

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 2/3

8:45 a.m.-6:37 p.m.

2 stops9h 52m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 319

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 1/12

2:55 p.m.-9:26 a.m.

3 stops18h 31m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 326

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 18/11

9:50 a.m.-11:25 a.m.

2 stops25h 35m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 351

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 1/12

8:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 363

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 5/12

8:00 p.m.-9:45 a.m.

2 stops37h 45m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 371

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Mon 30/11

8:10 a.m.-9:26 a.m.

3 stops49h 16m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 372

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 21/11

9:50 a.m.-8:14 a.m.

3 stops22h 24m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 412

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/10

Showing 1-10 of 19 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 8h 05m. 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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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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