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

Delta is the most popular carrier 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 2026

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Find the cheapest flights from Chicago Midway Airport to Calgary

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:27 am - 8:40 pm

MDW

YYC

12h 13m

2 stops

6:40 am - 1:32 pm

YYC

MDW

5h 52m

1 stop

$265Delta

Tue, Apr 21 - Tue, Apr 28

1:51 pm - 8:54 pm

MDW

YYC

8h 03m

1 stop

6:30 am - 4:14 pm

YYC

MDW

8h 44m

1 stop

$276Delta

Wed, Feb 11 - Sun, Feb 15

1:49 pm - 8:54 pm

MDW

YYC

8h 05m

1 stop

6:30 am - 1:05 pm

YYC

MDW

5h 35m

1 stop

$278Delta

Tue, Feb 17 - Thu, Feb 26

9:32 am - 8:54 pm

MDW

YYC

12h 22m

2 stops

6:30 am - 4:16 pm

YYC

MDW

8h 46m

1 stop

$280Delta

Wed, Feb 4 - Sat, Feb 7

9:33 am - 8:54 pm

MDW

YYC

12h 21m

2 stops

6:30 am - 4:14 pm

YYC

MDW

8h 44m

1 stop

$286Delta

Wed, Feb 11 - Sun, Feb 15

1:49 pm - 8:54 pm

MDW

YYC

8h 05m

1 stop

6:30 am - 5:37 pm

YYC

MDW

10h 07m

2 stops

$288Delta

Tue, Feb 17 - Fri, Feb 27

9:34 am - 8:54 pm

MDW

YYC

12h 20m

2 stops

6:30 am - 5:37 pm

YYC

MDW

10h 07m

2 stops

$293Delta

Tue, Feb 17 - Fri, Feb 27

7:00 am - 7:09 pm

MDW

YYC

13h 09m

1 stop

7:00 pm - 4:16 pm

YYC

MDW

20h 16m

2 stops

$296Multiple Airlines

Wed, Feb 18 - Wed, Feb 25

7:00 am - 7:09 pm

MDW

YYC

13h 09m

1 stop

12:30 am - 7:07 pm

YYC

MDW

17h 37m

1 stop

$298Multiple Airlines

Wed, Feb 18 - Mon, Feb 23

1:49 pm - 8:54 pm

MDW

YYC

8h 05m

1 stop

6:30 am - 1:05 pm

YYC

MDW

5h 35m

1 stop

$300Delta

Tue, Feb 17 - Mon, Feb 23

Delta flights from Chicago Midway Airport to Calgary

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

Delta

Apr 21

MDW9:27 amChicago Midway

12h 13m

2 stops

YYC8:40 pmCalgary

Apr 28

YYC6:40 amCalgary

5h 52m

1 stop

MDW1:32 pmChicago Midway

$265

Delta

Feb 11

MDW1:51 pmChicago Midway

8h 03m

1 stop

YYC8:54 pmCalgary

Feb 15

YYC6:30 amCalgary

8h 44m

1 stop

MDW4:14 pmChicago Midway

$276

Delta

Feb 17

MDW1:49 pmChicago Midway

8h 05m

1 stop

YYC8:54 pmCalgary

Feb 26

YYC6:30 amCalgary

5h 35m

1 stop

MDW1:05 pmChicago Midway

$278

WestJet flights from Chicago Midway Airport to Calgary

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

WestJet

Feb 1

MDW7:16 pmChicago Midway

26h 38m

1 stop

YYC8:54 pmCalgary

Feb 7

YYC6:30 amCalgary

8h 46m

1 stop

MDW4:16 pmChicago Midway

$912

WestJet

Jan 30

MDW9:50 amChicago Midway

10h 25m

2 stops

YYC7:15 pmCalgary

Feb 7

YYC6:30 amCalgary

8h 46m

1 stop

MDW4:16 pmChicago Midway

$959

WestJet

Jan 30

MDW1:49 pmChicago Midway

8h 05m

1 stop

YYC8:54 pmCalgary

Feb 7

YYC6:30 amCalgary

8h 46m

1 stop

MDW4:16 pmChicago Midway

$993

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 4/21

9:27 am-8:40 pm

2 stops12h 13m

Calgary

Tue 4/28

6:40 am-1:32 pm

1 stop5h 52m

$265

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 2/11

1:51 pm-8:54 pm

1 stop8h 03m

Calgary

Sun 2/15

6:30 am-4:14 pm

1 stop8h 44m

$276

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/17

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Thu 2/26

6:30 am-1:05 pm

1 stop5h 35m

$278

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 2/4

9:32 am-8:54 pm

2 stops12h 22m

Calgary

Sat 2/7

6:30 am-4:16 pm

1 stop8h 46m

$280

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 2/11

9:33 am-8:54 pm

2 stops12h 21m

Calgary

Sun 2/15

6:30 am-4:14 pm

1 stop8h 44m

$286

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/17

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Fri 2/27

6:30 am-5:37 pm

2 stops10h 07m

$288

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/17

9:34 am-8:54 pm

2 stops12h 20m

Calgary

Fri 2/27

6:30 am-5:37 pm

2 stops10h 07m

$293

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 2/18

7:00 am-7:09 pm

1 stop13h 09m

Calgary

Wed 2/25

7:00 pm-4:16 pm

2 stops20h 16m

$296

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 2/18

7:00 am-7:09 pm

1 stop13h 09m

Calgary

Mon 2/23

12:30 am-7:07 pm

1 stop17h 37m

$298

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/17

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Mon 2/23

6:30 am-1:05 pm

1 stop5h 35m

$300

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 Friday when prices can be found for as low as $292. 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 Wednesday will generally be more expensive and average around $322. 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 $263. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $445 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

Fastest flight time	6h 25m
Direct flights	None

The fastest flight from Chicago Midway Airport to Calgary takes 6h 25m

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 6h 25m, 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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Lake Louise

Airdrie

Drumheller

Radium Hot Springs

Kananaskis

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.