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

Delta 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 were last updated today.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for 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.

C$ 133 Cheap Flights from Chicago Midway Airport to Calgary in 2025/26

1 adult

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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.

2:49 p.m. - 11:44 a.m.MDW-YYC

21h 55m1 stop

9:45 p.m. - 1:59 p.m.YYC-MDW

15h 14m2 stops

C$ 306Multiple Airlines

Find Deal

Tue, 2 Dec - Fri, 5 Dec

7:23 p.m. - 7:09 p.m.MDW-YYC

24h 46m1 stop

12:30 a.m. - 10:12 p.m.YYC-MDW

20h 42m1 stop

C$ 318Multiple Airlines

Find Deal

Thu, 4 Dec - Sat, 6 Dec

6:15 a.m. - 7:09 p.m.MDW-YYC

13h 54m1 stop

8:15 p.m. - 10:12 p.m.YYC-MDW

24h 57m2 stops

C$ 323Multiple Airlines

Find Deal

Thu, 4 Dec - Sun, 7 Dec

8:42 p.m. - 11:44 a.m.MDW-YYC

16h 02m1 stop

9:45 p.m. - 5:38 p.m.YYC-MDW

18h 53m2 stops

C$ 341Multiple Airlines

Find Deal

Mon, 15 Dec - Wed, 24 Dec

1:50 p.m. - 8:57 p.m.MDW-YYC

8h 07m1 stop

6:35 a.m. - 1:10 p.m.YYC-MDW

5h 35m1 stop

C$ 351Delta

Find Deal

Wed, 10 Dec - Sat, 13 Dec

1:50 p.m. - 8:57 p.m.MDW-YYC

8h 07m1 stop

7:35 a.m. - 6:18 p.m.YYC-MDW

9h 43m2 stops

C$ 364Delta

Find Deal

Wed, 10 Dec - Sat, 13 Dec

9:34 a.m. - 8:57 p.m.MDW-YYC

12h 23m2 stops

7:35 a.m. - 6:18 p.m.YYC-MDW

9h 43m2 stops

C$ 371Delta

Find Deal

Wed, 10 Dec - Sat, 13 Dec

6:05 a.m. - 7:09 p.m.MDW-YYC

14h 04m1 stop

7:30 a.m. - 10:12 p.m.YYC-MDW

13h 42m2 stops

C$ 383Multiple Airlines

Find Deal

Thu, 27 Nov - Thu, 4 Dec

11:48 a.m. - 9:06 p.m.MDW-YYC

10h 18m1 stop

6:30 a.m. - 1:09 p.m.YYC-MDW

5h 39m1 stop

C$ 390Delta

Find Deal

Sun, 4 Jan - Fri, 9 Jan

7:23 p.m. - 7:09 p.m.MDW-YYC

24h 46m1 stop

7:35 p.m. - 2:52 p.m.YYC-MDW

18h 17m1 stop

C$ 401Multiple Airlines

Find Deal

Thu, 4 Dec - Sun, 7 Dec

Delta flights from Chicago Midway Airport to Calgary

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

Delta

10 Dec

MDW1:50 p.m.Chicago Midway

8h 07m

1 stop

YYC8:57 p.m.Calgary

13 Dec

YYC6:35 a.m.Calgary

5h 35m

1 stop

MDW1:10 p.m.Chicago Midway

C$ 350

Find similar

Delta

10 Dec

MDW1:50 p.m.Chicago Midway

8h 07m

1 stop

YYC8:57 p.m.Calgary

13 Dec

YYC7:35 a.m.Calgary

9h 43m

2 stops

MDW6:18 p.m.Chicago Midway

C$ 364

Find similar

Delta

10 Dec

MDW9:34 a.m.Chicago Midway

12h 23m

2 stops

YYC8:57 p.m.Calgary

13 Dec

YYC7:35 a.m.Calgary

9h 43m

2 stops

MDW6:18 p.m.Chicago Midway

C$ 371

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 2/12

2:49 p.m.-11:44 a.m.

1 stop21h 55m

Calgary

Fri 5/12

9:45 p.m.-1:59 p.m.

2 stops15h 14m

C$ 306

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 4/12

7:23 p.m.-7:09 p.m.

1 stop24h 46m

Calgary

Sat 6/12

12:30 a.m.-10:12 p.m.

1 stop20h 42m

C$ 318

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 4/12

6:15 a.m.-7:09 p.m.

1 stop13h 54m

Calgary

Sun 7/12

8:15 p.m.-10:12 p.m.

2 stops24h 57m

C$ 323

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 15/12

8:42 p.m.-11:44 a.m.

1 stop16h 02m

Calgary

Wed 24/12

9:45 p.m.-5:38 p.m.

2 stops18h 53m

C$ 341

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/12

1:50 p.m.-8:57 p.m.

1 stop8h 07m

Calgary

Sat 13/12

6:35 a.m.-1:10 p.m.

1 stop5h 35m

C$ 350

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/12

1:50 p.m.-8:57 p.m.

1 stop8h 07m

Calgary

Sat 13/12

7:35 a.m.-6:18 p.m.

2 stops9h 43m

C$ 364

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/12

9:34 a.m.-8:57 p.m.

2 stops12h 23m

Calgary

Sat 13/12

7:35 a.m.-6:18 p.m.

2 stops9h 43m

C$ 371

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 27/11

6:05 a.m.-7:09 p.m.

1 stop14h 04m

Calgary

Thu 4/12

7:30 a.m.-10:12 p.m.

2 stops13h 42m

C$ 383

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 4/1

11:48 a.m.-9:06 p.m.

1 stop10h 18m

Calgary

Fri 9/1

6:30 a.m.-1:09 p.m.

1 stop5h 39m

C$ 390

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 4/12

7:23 p.m.-7:09 p.m.

1 stop24h 46m

Calgary

Sun 7/12

7:35 p.m.-2:52 p.m.

1 stop18h 17m

C$ 401

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 Wednesday when prices can be found for as low as C$ 230. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 440.

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

Our data shows that the cheapest Chicago Midway Airport to Calgary flights are usually those with departure times in the evening. Our users have found flights to Calgary in the evening for as low as C$ 219. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 355 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 travellers’ 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?
Chicago Midway and Calgary are 2247.1 km apart from one another. Flights usually cover this in 8h 06m, 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 were last updated today.
How old do you have to be to fly from Chicago Midway Airport to Calgary Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for 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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Canmore

Lake Louise

Radium Hot Springs

Kananaskis

Drumheller

Airdrie

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Calgary from Chicago.

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

Flights from Chicago to Calgary with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Calgary.

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

If you are simply researching potential flights to Calgary, momondo offers a useful price alert feature which will track prices for flights to Calgary from Chicago and alert you when they change.