Cheap flights from Calgary to Chicago Midway Airport

YYC — MDW
5 Dec — 12 Dec1
Return
1 adult
Economy
From?
To?
Mon 5/12
Mon 12/12

How far in advance should I book a flight from Calgary to Chicago Midway Airport?

To save on the cost of your flight from Calgary to Chicago Midway Airport, book at least 61 days before your planned departure. Booking around this time can save you about 42% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 847 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 956.

What is the cheapest month to fly from Calgary to Chicago Midway Airport?

Our data shows that November tends to be the cheapest month to fly to Chicago Midway Airport from Calgary. Users have commonly found prices around C$ 673 for the month, but tickets can be as low as C$ 485. Due to multiple factors, prepare for potentially higher prices in July.

When is the cheapest time to fly from Calgary to Chicago Midway Airport (YYC - MDW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Calgary to Chicago Midway Airport as you normally would.

Cheap flights from Calgary to Midway in November, December 2022

The best prices found for YYC to MDW flights for November, December
13 Dec. - 18 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

11h 05m
MDW

Chicago Midway

YYC

Calgary

1 stop

15h 14m
C$ 493

Multiple Airlines

Deal found 29/11

11 Dec. - 18 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

10h 50m
MDW

Chicago Midway

YYC

Calgary

1 stop

9h 39m
C$ 521

Multiple Airlines

Deal found 27/11

10 Dec. - 18 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

17h 05m
MDW

Chicago Midway

YYC

Calgary

1 stop

9h 39m
C$ 524

Multiple Airlines

Deal found 27/11

Calgary to Midway 2022 flight deals

Cheap flights to Midway from Calgary found for this year
13 Dec. - 18 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

11h 05m
MDW

Chicago Midway

YYC

Calgary

1 stop

15h 14m
C$ 493

Multiple Airlines

Deal found 29/11

11 Dec. - 18 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

10h 50m
MDW

Chicago Midway

YYC

Calgary

1 stop

9h 39m
C$ 521

Multiple Airlines

Deal found 27/11

10 Dec. - 18 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

17h 05m
MDW

Chicago Midway

YYC

Calgary

1 stop

9h 39m
C$ 524

Multiple Airlines

Deal found 27/11

Cheap Delta flights from Calgary to Midway

10 Jan. - 21 Jan.
YYC

Calgary

MDW

Chicago Midway

1 stop

9h 55m
MDW

Chicago Midway

YYC

Calgary

2 stops

9h 04m
C$ 482

Delta

Deal found 30/11

17 Feb. - 24 Feb.
YYC

Calgary

MDW

Chicago Midway

1 stop

6h 15m
MDW

Chicago Midway

YYC

Calgary

1 stop

7h 28m
C$ 565

Delta

Deal found 28/11

5 Jan. - 14 Jan.
YYC

Calgary

MDW

Chicago Midway

1 stop

9h 34m
MDW

Chicago Midway

YYC

Calgary

2 stops

9h 04m
C$ 589

Delta

Deal found 28/11

Cheap Endeavor Airlines flights from Calgary to Midway

26 Jan. - 30 Jan.
YYC

Calgary

MDW

Chicago Midway

1 stop

6h 24m
MDW

Chicago Midway

YYC

Calgary

1 stop

8h 09m
C$ 896

Endeavor Airlines

Deal found 29/11

26 Jan. - 30 Jan.
YYC

Calgary

MDW

Chicago Midway

1 stop

6h 24m
MDW

Chicago Midway

YYC

Calgary

1 stop

8h 09m
C$ 901

Endeavor Airlines

Deal found 28/11

25 Dec. - 30 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

9h 34m
MDW

Chicago Midway

YYC

Calgary

1 stop

5h 31m
C$ 946

Endeavor Airlines

Deal found 29/11

Last minute flights from Calgary to Midway

Late deals on round-trip flights to Midway from Calgary, departing today and this week
10 Dec. - 13 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

17h 05m
MDW

Chicago Midway

YYC

Calgary

1 stop

15h 39m
C$ 440

Multiple Airlines

Deal found 27/11

10 Dec. - 18 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

17h 05m
MDW

Chicago Midway

YYC

Calgary

1 stop

9h 39m
C$ 524

Multiple Airlines

Deal found 27/11

10 Dec. - 18 Dec.
YYC

Calgary

MDW

Chicago Midway

1 stop

17h 05m
MDW

Chicago Midway

YYC

Calgary

1 stop

9h 39m
C$ 631

Multiple Airlines

Deal found 29/11

One-way flights to Midway from Calgary

The cheapest one-way flights from Calgary to Midway
2 Apr.
YYC

Calgary

MDW

Chicago Midway

1 stop

15h 47m
C$ 222

Multiple Airlines

Deal found 28/11

18 Jan.
YYC

Calgary

MDW

Chicago Midway

1 stop

14h 55m
C$ 262

Multiple Airlines

Deal found 29/11

19 Jan.
YYC

Calgary

MDW

Chicago Midway

1 stop

6h 24m
C$ 274

Delta

Deal found 29/11

Related info for your journey

Useful info, stats and facts about Calgary to Midway flights.

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.

Can I find flights from Calgary to Chicago Midway Airport for under C$ 500 on Cheapflights?

Yes, there are multiple flights from Calgary to Chicago Midway Airport for under C$ 500. The cheapest flight booked recently is on Multiple Airlines for just C$ 462, but on average you can expect to pay C$ 589.

Are there last-minute flights available from Calgary to Chicago Midway Airport for under C$ 500?

There are currently 10+ open flights from Calgary to Chicago Midway Airport within the next 7 days for less than C$ 500.

Alternative routes for Calgary to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Calgary to O'Hare Intlfrom C$ 649 pp
Edmonton to O'Hare Intlfrom C$ 2,901 pp