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

Delta, Porter Airlines, and WestJet 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

Round-trip

One-way

Last minute

Cheap round-trip flights

1:43 pm - 8:42 pmMDW-YYC

7h 59m1 stop

6:40 am - 5:35 pmYYC-MDW

9h 55m1 stop

$251Delta

Find Deal

Tue, Sep 30 - Fri, Oct 3

6:30 am - 5:06 pmMDW-YYC

11h 36m1 stop

8:15 pm - 11:38 amYYC-MDW

14h 23m2 stops

$254Multiple Airlines

Find Deal

Thu, Oct 30 - Mon, Nov 3

8:05 am - 8:00 pmMDW-YYC

12h 55m1 stop

12:30 am - 1:38 pmYYC-MDW

12h 08m1 stop

$256Multiple Airlines

Find Deal

Tue, Oct 21 - Tue, Oct 21

6:30 am - 5:06 pmMDW-YYC

11h 36m1 stop

8:55 am - 12:41 pmYYC-MDW

26h 46m1 stop

$258Multiple Airlines

Find Deal

Thu, Nov 6 - Tue, Nov 11

10:00 am - 6:21 pmMDW-YYC

9h 21m1 stop

7:00 am - 11:46 pmYYC-MDW

15h 46m2 stops

$259Multiple Airlines

Find Deal

Sat, Oct 18 - Fri, Oct 24

9:20 am - 1:54 pmMDW-YYC

5h 34m1 stop

6:20 am - 6:08 pmYYC-MDW

10h 48m2 stops

$261Delta

Find Deal

Sat, Nov 8 - Sat, Nov 15

9:20 am - 1:54 pmMDW-YYC

5h 34m1 stop

6:20 am - 1:07 pmYYC-MDW

5h 47m1 stop

$262Delta

Find Deal

Sat, Nov 8 - Sat, Nov 15

11:10 am - 8:47 pmMDW-YYC

10h 37m2 stops

7:45 am - 6:18 pmYYC-MDW

9h 33m2 stops

$266Delta

Find Deal

Sat, Nov 8 - Sat, Nov 15

6:30 am - 5:06 pmMDW-YYC

11h 36m1 stop

11:30 pm - 6:39 pmYYC-MDW

42h 09m2 stops

$270Multiple Airlines

Find Deal

Thu, Nov 6 - Tue, Nov 11

3:00 pm - 8:47 pmMDW-YYC

6h 47m1 stop

6:20 am - 6:08 pmYYC-MDW

10h 48m2 stops

$271Delta

Find Deal

Sat, Nov 8 - Sat, Nov 15

Delta flights from Chicago Midway Airport to Calgary

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

Delta

Sep 30

MDW1:43 pmChicago Midway

7h 59m

1 stop

YYC8:42 pmCalgary

Oct 3

YYC6:40 amCalgary

9h 55m

1 stop

MDW5:35 pmChicago Midway

$251

Find similar

Delta

Nov 8

MDW9:20 amChicago Midway

5h 34m

1 stop

YYC1:54 pmCalgary

Nov 15

YYC6:20 amCalgary

10h 48m

2 stops

MDW6:08 pmChicago Midway

$261

Find similar

Delta

Nov 8

MDW9:20 amChicago Midway

5h 34m

1 stop

YYC1:54 pmCalgary

Nov 15

YYC6:20 amCalgary

5h 47m

1 stop

MDW1:07 pmChicago Midway

$262

Find similar

WestJet flights from Chicago Midway Airport to Calgary

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

WestJet

Sep 28

MDW7:15 pmChicago Midway

30h 29m

2 stops

YYC12:44 amCalgary

Oct 1

YYC6:00 amCalgary

10h 35m

2 stops

MDW5:35 pmChicago Midway

$698

Find similar

WestJet

Sep 30

MDW9:20 amChicago Midway

24h 30m

2 stops

YYC8:50 amCalgary

Oct 7

YYC6:30 pmCalgary

17h 38m

2 stops

MDW1:08 pmChicago Midway

$701

Find similar

WestJet

Sep 28

MDW9:20 amChicago Midway

25h 24m

2 stops

YYC9:44 amCalgary

Sep 29

YYC9:30 pmCalgary

14h 33m

2 stops

MDW1:03 pmChicago Midway

$717

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

Tue 9/30

1:43 pm-8:42 pm

1 stop7h 59m

Calgary

Fri 10/3

6:40 am-5:35 pm

1 stop9h 55m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 10/30

6:30 am-5:06 pm

1 stop11h 36m

Calgary

Mon 11/3

8:15 pm-11:38 am

2 stops14h 23m

$254

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 10/21

8:05 am-8:00 pm

1 stop12h 55m

Calgary

Tue 10/21

12:30 am-1:38 pm

1 stop12h 08m

$256

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 11/6

6:30 am-5:06 pm

1 stop11h 36m

Calgary

Tue 11/11

8:55 am-12:41 pm

1 stop26h 46m

$258

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 10/18

10:00 am-6:21 pm

1 stop9h 21m

Calgary

Fri 10/24

7:00 am-11:46 pm

2 stops15h 46m

$259

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

9:20 am-1:54 pm

1 stop5h 34m

Calgary

Sat 11/15

6:20 am-6:08 pm

2 stops10h 48m

$261

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

9:20 am-1:54 pm

1 stop5h 34m

Calgary

Sat 11/15

6:20 am-1:07 pm

1 stop5h 47m

$262

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

11:10 am-8:47 pm

2 stops10h 37m

Calgary

Sat 11/15

7:45 am-6:18 pm

2 stops9h 33m

$266

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 11/6

6:30 am-5:06 pm

1 stop11h 36m

Calgary

Tue 11/11

11:30 pm-6:39 pm

2 stops42h 09m

$270

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

3:00 pm-8:47 pm

1 stop6h 47m

Calgary

Sat 11/15

6:20 am-6:08 pm

2 stops10h 48m

$271

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 $332. 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 at noon when flights can be purchased for as low as $204. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $471 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.