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 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

1:43 p.m. - 8:42 p.m.MDW-YYC

7h 59m1 stop

6:40 a.m. - 5:35 p.m.YYC-MDW

9h 55m1 stop

C$ 345Delta

Find Deal

Tue, 30 Sep - Sat, 4 Oct

6:30 a.m. - 5:06 p.m.MDW-YYC

11h 36m1 stop

8:15 p.m. - 11:38 a.m.YYC-MDW

14h 23m2 stops

C$ 349Multiple Airlines

Find Deal

Thu, 30 Oct - Mon, 3 Nov

8:05 a.m. - 12:44 a.m.MDW-YYC

17h 39m2 stops

12:30 a.m. - 1:38 p.m.YYC-MDW

12h 08m1 stop

C$ 352Multiple Airlines

Find Deal

Wed, 15 Oct - Tue, 21 Oct

6:30 a.m. - 5:06 p.m.MDW-YYC

11h 36m1 stop

8:55 a.m. - 12:41 p.m.YYC-MDW

26h 46m1 stop

C$ 355Multiple Airlines

Find Deal

Thu, 6 Nov - Tue, 11 Nov

10:00 a.m. - 6:21 p.m.MDW-YYC

9h 21m1 stop

7:00 a.m. - 11:46 p.m.YYC-MDW

15h 46m2 stops

C$ 356Multiple Airlines

Find Deal

Sat, 18 Oct - Fri, 24 Oct

9:20 a.m. - 1:54 p.m.MDW-YYC

5h 34m1 stop

6:20 a.m. - 6:08 p.m.YYC-MDW

10h 48m2 stops

C$ 359Delta

Find Deal

Sat, 8 Nov - Sat, 15 Nov

9:20 a.m. - 1:54 p.m.MDW-YYC

5h 34m1 stop

6:20 a.m. - 1:07 p.m.YYC-MDW

5h 47m1 stop

C$ 360Delta

Find Deal

Sat, 8 Nov - Sat, 15 Nov

11:10 a.m. - 8:47 p.m.MDW-YYC

10h 37m2 stops

7:45 a.m. - 6:18 p.m.YYC-MDW

9h 33m2 stops

C$ 366Delta

Find Deal

Sat, 8 Nov - Sat, 15 Nov

6:30 a.m. - 5:06 p.m.MDW-YYC

11h 36m1 stop

11:30 p.m. - 6:39 p.m.YYC-MDW

42h 09m2 stops

C$ 371Multiple Airlines

Find Deal

Thu, 6 Nov - Tue, 11 Nov

3:00 p.m. - 8:47 p.m.MDW-YYC

6h 47m1 stop

6:20 a.m. - 6:08 p.m.YYC-MDW

10h 48m2 stops

C$ 373Delta

Find Deal

Sat, 8 Nov - Sat, 15 Nov

Delta flights from Chicago Midway Airport to Calgary

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

Delta

30 Sep

MDW1:43 p.m.Chicago Midway

7h 59m

1 stop

YYC8:42 p.m.Calgary

4 Oct

YYC6:40 a.m.Calgary

9h 55m

1 stop

MDW5:35 p.m.Chicago Midway

C$ 345

Find similar

Delta

8 Nov

MDW9:20 a.m.Chicago Midway

5h 34m

1 stop

YYC1:54 p.m.Calgary

15 Nov

YYC6:20 a.m.Calgary

10h 48m

2 stops

MDW6:08 p.m.Chicago Midway

C$ 359

Find similar

Delta

8 Nov

MDW9:20 a.m.Chicago Midway

5h 34m

1 stop

YYC1:54 p.m.Calgary

15 Nov

YYC6:20 a.m.Calgary

5h 47m

1 stop

MDW1:07 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

28 Sep

MDW7:15 p.m.Chicago Midway

30h 29m

2 stops

YYC12:44 a.m.Calgary

1 Oct

YYC6:00 a.m.Calgary

10h 35m

2 stops

MDW5:35 p.m.Chicago Midway

C$ 960

Find similar

WestJet

30 Sep

MDW9:20 a.m.Chicago Midway

24h 30m

2 stops

YYC8:50 a.m.Calgary

7 Oct

YYC6:30 p.m.Calgary

17h 38m

2 stops

MDW1:08 p.m.Chicago Midway

C$ 964

Find similar

WestJet

28 Sep

MDW9:20 a.m.Chicago Midway

25h 24m

2 stops

YYC9:44 a.m.Calgary

29 Sep

YYC9:30 p.m.Calgary

14h 33m

2 stops

MDW1:03 p.m.Chicago Midway

C$ 986

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 30/9

1:43 p.m.-8:42 p.m.

1 stop7h 59m

Calgary

Sat 4/10

6:40 a.m.-5:35 p.m.

1 stop9h 55m

C$ 345

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 30/10

6:30 a.m.-5:06 p.m.

1 stop11h 36m

Calgary

Mon 3/11

8:15 p.m.-11:38 a.m.

2 stops14h 23m

C$ 349

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 15/10

8:05 a.m.-12:44 a.m.

2 stops17h 39m

Calgary

Tue 21/10

12:30 a.m.-1:38 p.m.

1 stop12h 08m

C$ 352

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 6/11

6:30 a.m.-5:06 p.m.

1 stop11h 36m

Calgary

Tue 11/11

8:55 a.m.-12:41 p.m.

1 stop26h 46m

C$ 355

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 18/10

10:00 a.m.-6:21 p.m.

1 stop9h 21m

Calgary

Fri 24/10

7:00 a.m.-11:46 p.m.

2 stops15h 46m

C$ 356

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 8/11

9:20 a.m.-1:54 p.m.

1 stop5h 34m

Calgary

Sat 15/11

6:20 a.m.-6:08 p.m.

2 stops10h 48m

C$ 359

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 8/11

9:20 a.m.-1:54 p.m.

1 stop5h 34m

Calgary

Sat 15/11

6:20 a.m.-1:07 p.m.

1 stop5h 47m

C$ 360

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 8/11

11:10 a.m.-8:47 p.m.

2 stops10h 37m

Calgary

Sat 15/11

7:45 a.m.-6:18 p.m.

2 stops9h 33m

C$ 366

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 6/11

6:30 a.m.-5:06 p.m.

1 stop11h 36m

Calgary

Tue 11/11

11:30 p.m.-6:39 p.m.

2 stops42h 09m

C$ 371

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 8/11

3:00 p.m.-8:47 p.m.

1 stop6h 47m

Calgary

Sat 15/11

6:20 a.m.-6:08 p.m.

2 stops10h 48m

C$ 373

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$ 433.

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$ 216. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 315 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 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 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.