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 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$ 138 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.

11:45 a.m. - 8:54 p.m.

MDW

YYC

10h 09m1 stop

6:30 a.m. - 1:06 p.m.

YYC

MDW

5h 36m1 stop

C$ 346Delta

Sat, 31 Jan - Tue, 3 Feb

11:45 a.m. - 8:54 p.m.

MDW

YYC

10h 09m1 stop

6:30 a.m. - 4:14 p.m.

YYC

MDW

8h 44m1 stop

C$ 347Delta

Sun, 8 Feb - Sat, 14 Feb

11:45 a.m. - 11:02 p.m.

MDW

YYC

12h 17m2 stops

6:30 a.m. - 4:14 p.m.

YYC

MDW

8h 44m1 stop

C$ 360Delta

Sun, 8 Feb - Sat, 14 Feb

9:33 a.m. - 8:54 p.m.

MDW

YYC

12h 21m2 stops

6:30 a.m. - 5:55 p.m.

YYC

MDW

10h 25m2 stops

C$ 366Delta

Sat, 31 Jan - Tue, 3 Feb

1:49 p.m. - 8:54 p.m.

MDW

YYC

8h 05m1 stop

6:30 a.m. - 1:07 p.m.

YYC

MDW

5h 37m1 stop

C$ 386Delta

Mon, 2 Mar - Fri, 6 Mar

5:01 p.m. - 11:44 a.m.

MDW

YYC

19h 43m1 stop

9:45 p.m. - 12:05 p.m.

YYC

MDW

13h 20m2 stops

C$ 387Multiple Airlines

Thu, 22 Jan - Mon, 26 Jan

6:20 a.m. - 7:09 p.m.

MDW

YYC

13h 49m1 stop

8:15 p.m. - 11:45 a.m.

YYC

MDW

14h 30m2 stops

C$ 389Multiple Airlines

Thu, 22 Jan - Sun, 25 Jan

1:49 p.m. - 8:54 p.m.

MDW

YYC

8h 05m1 stop

6:30 a.m. - 1:07 p.m.

YYC

MDW

5h 37m1 stop

C$ 393Delta

Mon, 2 Mar - Fri, 6 Mar

9:32 a.m. - 8:54 p.m.

MDW

YYC

12h 22m2 stops

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

YYC

MDW

5h 39m1 stop

C$ 398Delta

Thu, 22 Jan - Sun, 25 Jan

9:30 a.m. - 6:25 p.m.

MDW

YYC

9h 55m1 stop

9:15 a.m. - 6:31 p.m.

YYC

MDW

8h 16m1 stop

C$ 409Delta

Sat, 23 May - Sat, 30 May

Delta flights from Chicago Midway Airport to Calgary

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

Delta

31 Jan

MDW11:45 a.m.Chicago Midway

10h 09m

1 stop

YYC8:54 p.m.Calgary

3 Feb

YYC6:30 a.m.Calgary

5h 36m

1 stop

MDW1:06 p.m.Chicago Midway

C$ 346

Find similar

Delta

8 Feb

MDW11:45 a.m.Chicago Midway

10h 09m

1 stop

YYC8:54 p.m.Calgary

14 Feb

YYC6:30 a.m.Calgary

8h 44m

1 stop

MDW4:14 p.m.Chicago Midway

C$ 347

Find similar

Delta

31 Jan

MDW9:33 a.m.Chicago Midway

12h 21m

2 stops

YYC8:54 p.m.Calgary

7 Feb

YYC6:30 a.m.Calgary

8h 46m

1 stop

MDW4:16 p.m.Chicago Midway

C$ 360

Find similar

WestJet flights from Chicago Midway Airport to Calgary

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

WestJet

29 Dec

MDW9:29 a.m.Chicago Midway

12h 33m

2 stops

YYC9:02 p.m.Calgary

6 Jan

YYC5:15 p.m.Calgary

18h 33m

2 stops

MDW12:48 p.m.Chicago Midway

C$ 1,200

Find similar

WestJet

26 Dec

MDW9:29 a.m.Chicago Midway

16h 15m

2 stops

YYC12:44 a.m.Calgary

31 Dec

YYC8:15 p.m.Calgary

11h 50m

2 stops

MDW9:05 a.m.Chicago Midway

C$ 1,239

Find similar

WestJet

26 Dec

MDW9:29 a.m.Chicago Midway

12h 33m

2 stops

YYC9:02 p.m.Calgary

28 Dec

YYC9:00 a.m.Calgary

23h 05m

2 stops

MDW9:05 a.m.Chicago Midway

C$ 1,274

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

Sat 31/1

11:45 a.m.-8:54 p.m.

1 stop10h 09m

Calgary

Tue 3/2

6:30 a.m.-1:06 p.m.

1 stop5h 36m

C$ 346

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 8/2

11:45 a.m.-8:54 p.m.

1 stop10h 09m

Calgary

Sat 14/2

6:30 a.m.-4:14 p.m.

1 stop8h 44m

C$ 347

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 8/2

11:45 a.m.-11:02 p.m.

2 stops12h 17m

Calgary

Sat 14/2

6:30 a.m.-4:14 p.m.

1 stop8h 44m

C$ 360

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 31/1

9:33 a.m.-8:54 p.m.

2 stops12h 21m

Calgary

Tue 3/2

6:30 a.m.-5:55 p.m.

2 stops10h 25m

C$ 366

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 2/3

1:49 p.m.-8:54 p.m.

1 stop8h 05m

Calgary

Fri 6/3

6:30 a.m.-1:07 p.m.

1 stop5h 37m

C$ 386

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 22/1

5:01 p.m.-11:44 a.m.

1 stop19h 43m

Calgary

Mon 26/1

9:45 p.m.-12:05 p.m.

2 stops13h 20m

C$ 387

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 22/1

6:20 a.m.-7:09 p.m.

1 stop13h 49m

Calgary

Sun 25/1

8:15 p.m.-11:45 a.m.

2 stops14h 30m

C$ 389

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 2/3

1:49 p.m.-8:54 p.m.

1 stop8h 05m

Calgary

Fri 6/3

6:30 a.m.-1:07 p.m.

1 stop5h 37m

C$ 393

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 22/1

9:32 a.m.-8:54 p.m.

2 stops12h 22m

Calgary

Sun 25/1

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

1 stop5h 39m

C$ 398

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 23/5

9:30 a.m.-6:25 p.m.

1 stop9h 55m

Calgary

Sat 30/5

9:15 a.m.-6:31 p.m.

1 stop8h 16m

C$ 409

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$ 227. 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$ 434.

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$ 217. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 353 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

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?
Chicago Midway and Calgary are 2247.1 km apart from one another. 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 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.

Banff

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.