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Cheap flights from Chicago Midway Airport to Calgary from C$ 163

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Calgary departing on 23/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Find the cheapest flights from Chicago Midway Airport to Calgary

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
2:12 p.m. - 8:40 p.m.
MDW
-
YYC
7h 28m
1 stop
Delta Logo
6:45 a.m. - 1:19 p.m.
YYC
-
MDW
5h 34m
1 stop
C$ 403Delta
Sat, 2 May - Sat, 9 May
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
Delta Logo
6:45 a.m. - 1:19 p.m.
YYC
-
MDW
5h 34m
1 stop
C$ 417Delta
Sat, 2 May - Sat, 9 May
Delta Logo
2:12 p.m. - 8:40 p.m.
MDW
-
YYC
7h 28m
1 stop
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m
1 stop
C$ 418Delta
Tue, 14 Apr - Sat, 18 Apr
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
Delta Logo
7:45 a.m. - 6:33 p.m.
YYC
-
MDW
9h 48m
2 stops
C$ 424Delta
Sat, 2 May - Sat, 9 May
Delta Logo
2:12 p.m. - 8:40 p.m.
MDW
-
YYC
7h 28m
1 stop
Delta Logo
6:40 a.m. - 10:28 p.m.
YYC
-
MDW
14h 48m
2 stops
C$ 429Delta
Tue, 14 Apr - Wed, 22 Apr
Delta Logo
2:12 p.m. - 8:40 p.m.
MDW
-
YYC
7h 28m
1 stop
Delta Logo
7:40 a.m. - 6:36 p.m.
YYC
-
MDW
9h 56m
2 stops
C$ 432Delta
Tue, 14 Apr - Sat, 18 Apr
Delta Logo
9:29 a.m. - 11:00 p.m.
MDW
-
YYC
14h 31m
2 stops
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m
1 stop
C$ 438Delta
Mon, 27 Apr - Tue, 5 May
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
Delta Logo
7:40 a.m. - 6:36 p.m.
YYC
-
MDW
9h 56m
2 stops
C$ 439Delta
Tue, 14 Apr - Sat, 18 Apr
Delta Logo
9:29 a.m. - 11:00 p.m.
MDW
-
YYC
14h 31m
2 stops
Delta Logo
7:40 a.m. - 10:28 p.m.
YYC
-
MDW
13h 48m
2 stops
C$ 445Delta
Mon, 27 Apr - Tue, 5 May
Delta Logo
1:49 p.m. - 8:38 p.m.
MDW
-
YYC
7h 49m
1 stop
Delta Logo
6:45 a.m. - 1:09 p.m.
YYC
-
MDW
5h 24m
1 stop
C$ 447Delta
Tue, 23 Jun - Wed, 1 Jul

Delta flights from Chicago Midway Airport to Calgary

Our best Delta deals on Chicago Midway Airport to Calgary flight tickets
Delta
2 May
MDW2:12 p.m.Chicago Midway
7h 28m
1 stop
YYC8:40 p.m.Calgary
9 May
YYC6:45 a.m.Calgary
5h 34m
1 stop
MDW1:19 p.m.Chicago Midway
C$ 403
Delta
11 Apr
MDW1:10 p.m.Chicago Midway
10h 52m
2 stops
YYC11:02 p.m.Calgary
14 Apr
YYC7:40 a.m.Calgary
13h 48m
2 stops
MDW10:28 p.m.Chicago Midway
C$ 408
Delta
2 May
MDW9:27 a.m.Chicago Midway
12h 13m
2 stops
YYC8:40 p.m.Calgary
9 May
YYC6:45 a.m.Calgary
5h 34m
1 stop
MDW1:19 p.m.Chicago Midway
C$ 417

WestJet flights from Chicago Midway Airport to Calgary

Our best WestJet deals on Chicago Midway Airport to Calgary flight tickets
WestJet
7 Apr
MDW9:35 a.m.Chicago Midway
10h 53m
2 stops
YYC7:28 p.m.Calgary
10 Apr
YYC6:30 a.m.Calgary
5h 54m
1 stop
MDW1:24 p.m.Chicago Midway
C$ 1,314
WestJet
2 Apr
MDW1:10 p.m.Chicago Midway
20h 52m
2 stops
YYC9:02 a.m.Calgary
4 Apr
YYC12:30 a.m.Calgary
8h 26m
1 stop
MDW9:56 a.m.Chicago Midway
C$ 1,335
WestJet
3 Apr
MDW6:34 p.m.Chicago Midway
15h 28m
2 stops
YYC9:02 a.m.Calgary
4 Apr
YYC12:30 a.m.Calgary
8h 26m
1 stop
MDW9:56 a.m.Chicago Midway
C$ 1,336

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Calgary that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 28 March 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/5

2:12 p.m.-8:40 p.m.

1 stop7h 28m

Calgary

Sat 9/5

6:45 a.m.-1:19 p.m.

1 stop5h 34m

C$ 403

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/5

9:27 a.m.-8:40 p.m.

2 stops12h 13m

Calgary

Sat 9/5

6:45 a.m.-1:19 p.m.

1 stop5h 34m

C$ 417

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 14/4

2:12 p.m.-8:40 p.m.

1 stop7h 28m

Calgary

Sat 18/4

6:40 a.m.-1:32 p.m.

1 stop5h 52m

C$ 418

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/5

9:27 a.m.-8:40 p.m.

2 stops12h 13m

Calgary

Sat 9/5

7:45 a.m.-6:33 p.m.

2 stops9h 48m

C$ 424

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 14/4

2:12 p.m.-8:40 p.m.

1 stop7h 28m

Calgary

Wed 22/4

6:40 a.m.-10:28 p.m.

2 stops14h 48m

C$ 429

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 14/4

2:12 p.m.-8:40 p.m.

1 stop7h 28m

Calgary

Sat 18/4

7:40 a.m.-6:36 p.m.

2 stops9h 56m

C$ 432

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 27/4

9:29 a.m.-11:00 p.m.

2 stops14h 31m

Calgary

Tue 5/5

6:40 a.m.-1:32 p.m.

1 stop5h 52m

C$ 438

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 14/4

9:27 a.m.-8:40 p.m.

2 stops12h 13m

Calgary

Sat 18/4

7:40 a.m.-6:36 p.m.

2 stops9h 56m

C$ 439

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 27/4

9:29 a.m.-11:00 p.m.

2 stops14h 31m

Calgary

Tue 5/5

7:40 a.m.-10:28 p.m.

2 stops13h 48m

C$ 445

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 23/6

1:49 p.m.-8:38 p.m.

1 stop7h 49m

Calgary

Wed 1/7

6:45 a.m.-1:09 p.m.

1 stop5h 24m

C$ 447

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Calgary from

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

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 C$ 234. 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$ 497.

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$ 356 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.

Can stopping save me money on Chicago Midway Airport to Calgary flights?

You could potentially save up to 62% on your flight if you consider stops on a Chicago Midway Airport to Calgary flight.

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

5h 20m

Direct flights

None
The fastest flight from Chicago Midway Airport to Calgary takes 5h 20m
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 20m, 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.

Travelling to a place near Calgary?

Book flights to Calgary if you plan to visit one of these locations
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.

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