What is the cheapest airline that flies from Chicago Midway to Calgary?

Delta and Porter Airlines are the most popular carriers operating from Chicago Midway to Calgary

When did momondo last update prices for flights from Chicago Midway Airport to Calgary Airport?

Prices for flights from Chicago Midway Airport to Calgary Airport are refreshed on a daily basis.

How old do you have to be to fly from Chicago Midway Airport to Calgary Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Calgary Airport.

What documentation or ID do you need to fly to Calgary Airport?

The travel and health documents you'll need for your trip to Calgary Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Calgary Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$100 Cheap Flights from Chicago Midway Airport to Calgary in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Calgary

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Cheap round-trip flights

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8:42 pm - 3:10 pmMDW-YYC

19h 28m2 stops

7:30 am - 10:18 pmYYC-MDW

13h 48m1 stop

$235Multiple Airlines

Find Deal

Fri, Dec 5 - Mon, Dec 8

1:56 pm - 11:44 amMDW-YYC

22h 48m1 stop

7:30 am - 10:17 pmYYC-MDW

13h 47m1 stop

$241Multiple Airlines

Find Deal

Tue, Nov 11 - Thu, Nov 27

8:42 pm - 7:09 pmMDW-YYC

23h 27m1 stop

9:45 pm - 9:22 pmYYC-MDW

22h 37m2 stops

$243Multiple Airlines

Find Deal

Fri, Dec 5 - Fri, Dec 12

12:30 pm - 10:52 pmMDW-YYC

11h 22m1 stop

12:20 pm - 9:44 pmYYC-MDW

8h 24m1 stop

$249Multiple Airlines

Find Deal

Thu, Jan 15 - Sun, Jan 18

6:15 am - 7:09 pmMDW-YYC

13h 54m1 stop

7:30 am - 10:18 pmYYC-MDW

13h 48m1 stop

$250Multiple Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

1:50 pm - 8:57 pmMDW-YYC

8h 07m1 stop

6:35 am - 1:08 pmYYC-MDW

5h 33m1 stop

$251Delta

Find Deal

Wed, Dec 10 - Sat, Dec 13

6:05 am - 7:09 pmMDW-YYC

14h 04m1 stop

8:55 am - 6:08 pmYYC-MDW

8h 13m1 stop

$254Multiple Airlines

Find Deal

Fri, Nov 28 - Thu, Dec 4

9:34 am - 8:53 pmMDW-YYC

12h 19m2 stops

6:35 am - 1:07 pmYYC-MDW

5h 32m1 stop

$260Delta

Find Deal

Tue, Nov 11 - Mon, Nov 24

1:50 pm - 8:57 pmMDW-YYC

8h 07m1 stop

7:35 am - 6:18 pmYYC-MDW

9h 43m2 stops

$261Delta

Find Deal

Sat, Dec 6 - Sat, Dec 13

11:05 am - 11:13 pmMDW-YYC

13h 08m2 stops

7:35 am - 6:18 pmYYC-MDW

9h 43m2 stops

$266Delta

Find Deal

Sat, Dec 6 - Sat, Dec 13

Delta flights from Chicago Midway Airport to Calgary

Our best Delta deals on Chicago Midway Airport to Calgary flight tickets

Delta

Dec 10

MDW1:50 pmChicago Midway

8h 07m

1 stop

YYC8:57 pmCalgary

Dec 13

YYC6:35 amCalgary

5h 33m

1 stop

MDW1:08 pmChicago Midway

$251

Find similar

Delta

Nov 11

MDW9:34 amChicago Midway

12h 19m

2 stops

YYC8:53 pmCalgary

Nov 24

YYC6:35 amCalgary

5h 32m

1 stop

MDW1:07 pmChicago Midway

$260

Find similar

Delta

Dec 6

MDW1:50 pmChicago Midway

8h 07m

1 stop

YYC8:57 pmCalgary

Dec 13

YYC7:35 amCalgary

9h 43m

2 stops

MDW6:18 pmChicago Midway

$261

Find similar

WestJet flights from Chicago Midway Airport to Calgary

Our best WestJet deals on Chicago Midway Airport to Calgary flight tickets

WestJet

Nov 6

MDW10:40 amChicago Midway

11h 22m

2 stops

YYC9:02 pmCalgary

Nov 10

YYC9:45 pmCalgary

11h 07m

2 stops

MDW9:52 amChicago Midway

$804

Find similar

WestJet

Nov 6

MDW10:40 amChicago Midway

11h 22m

2 stops

YYC9:02 pmCalgary

Nov 10

YYC6:35 amCalgary

10h 43m

1 stop

MDW6:18 pmChicago Midway

$808

Find similar

WestJet

Nov 6

MDW9:20 amChicago Midway

12h 42m

2 stops

YYC9:02 pmCalgary

Nov 10

YYC7:00 amCalgary

10h 18m

2 stops

MDW6:18 pmChicago Midway

$832

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Calgary that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 12/5

8:42 pm-3:10 pm

2 stops19h 28m

Calgary

Mon 12/8

7:30 am-10:18 pm

1 stop13h 48m

$235

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/11

1:56 pm-11:44 am

1 stop22h 48m

Calgary

Thu 11/27

7:30 am-10:17 pm

1 stop13h 47m

$241

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 12/5

8:42 pm-7:09 pm

1 stop23h 27m

Calgary

Fri 12/12

9:45 pm-9:22 pm

2 stops22h 37m

$243

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 1/15

12:30 pm-10:52 pm

1 stop11h 22m

Calgary

Sun 1/18

12:20 pm-9:44 pm

1 stop8h 24m

$249

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 12/4

6:15 am-7:09 pm

1 stop13h 54m

Calgary

Mon 12/8

7:30 am-10:18 pm

1 stop13h 48m

$250

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 12/10

1:50 pm-8:57 pm

1 stop8h 07m

Calgary

Sat 12/13

6:35 am-1:08 pm

1 stop5h 33m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 11/28

6:05 am-7:09 pm

1 stop14h 04m

Calgary

Thu 12/4

8:55 am-6:08 pm

1 stop8h 13m

$254

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/11

9:34 am-8:53 pm

2 stops12h 19m

Calgary

Mon 11/24

6:35 am-1:07 pm

1 stop5h 32m

$260

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 12/6

1:50 pm-8:57 pm

1 stop8h 07m

Calgary

Sat 12/13

7:35 am-6:18 pm

2 stops9h 43m

$261

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 12/6

11:05 am-11:13 pm

2 stops13h 08m

Calgary

Sat 12/13

7:35 am-6:18 pm

2 stops9h 43m

$266

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Calgary

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest day to depart on your flight to Calgary?

The cheapest day to depart on your flight to Calgary is on a Thursday when prices can be found for as low as $291. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago Midway Airport to Calgary on a Tuesday will generally be more expensive and average around $328. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Calgary?

The cheapest time of day to fly to Calgary is in the afternoon when flights can be purchased for as low as $262. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $482 on average. Flights to Calgary from Chicago Midway Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

When to book flights from Chicago Midway Airport to Calgary

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Calgary according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Calgary (MDW to YYC) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Calgary

Direct flights	None

There are no direct flights from Chicago Midway Airport to Calgary. There are no popular flight routes from Chicago Midway Airport to Calgary.

Search flight deals

How far is Chicago Midway to Calgary by plane?
There are 1396.3 mi between Chicago Midway and Calgary. Flights usually cover this in 5h 34m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to Calgary Airport?
Prices for flights from Chicago Midway Airport to Calgary Airport are refreshed on a daily basis.
How old do you have to be to fly from Chicago Midway Airport to Calgary Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Calgary Airport.
What documentation or ID do you need to fly to Calgary Airport?
The travel and health documents you'll need for your trip to Calgary Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Calgary Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Calgary?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Calgary. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Calgary with flexible booking policies on momondo?

momondo does allow users to show only those flights to Calgary from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Calgary?

momondo helps you find the best flight between Chicago and Calgary by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Calgary right now. Can momondo alert me if prices change?

Price alerts on flights to Calgary from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.