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Cheap flights from Chicago Midway Airport to Calgary from C$ 174

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 20/10. 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.
Multiple Airlines Logo
6:00 a.m. - 9:50 p.m.
MDW
-
YYC
16h 50m
1 stop
Multiple Airlines Logo
12:30 a.m. - 11:12 a.m.
YYC
-
MDW
9h 42m
1 stop
C$ 462Multiple Airlines
Tue, 11 Aug - Mon, 17 Aug
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
Multiple Airlines Logo
9:00 p.m. - 10:11 p.m.
YYC
-
MDW
24h 11m
2 stops
C$ 475Multiple Airlines
Tue, 11 Aug - Tue, 18 Aug
Multiple Airlines Logo
12:11 p.m. - 5:10 p.m.
MDW
-
YYC
29h 59m
1 stop
Multiple Airlines Logo
12:30 a.m. - 11:07 a.m.
YYC
-
MDW
9h 37m
1 stop
C$ 493Multiple Airlines
Thu, 30 Jul - Mon, 3 Aug
Multiple Airlines Logo
12:11 p.m. - 5:10 p.m.
MDW
-
YYC
29h 59m
1 stop
Multiple Airlines Logo
9:00 p.m. - 11:07 a.m.
YYC
-
MDW
13h 07m
2 stops
C$ 511Multiple Airlines
Thu, 30 Jul - Wed, 5 Aug
Multiple Airlines Logo
12:27 p.m. - 9:50 p.m.
MDW
-
YYC
10h 23m
1 stop
Multiple Airlines Logo
12:30 a.m. - 11:07 a.m.
YYC
-
MDW
9h 37m
1 stop
C$ 518Multiple Airlines
Tue, 30 Jun - Tue, 7 Jul
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
Multiple Airlines Logo
7:00 a.m. - 10:11 p.m.
YYC
-
MDW
14h 11m
1 stop
C$ 525Multiple Airlines
Tue, 11 Aug - Wed, 19 Aug
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
Multiple Airlines Logo
12:30 a.m. - 11:12 a.m.
YYC
-
MDW
9h 42m
1 stop
C$ 530Multiple Airlines
Tue, 11 Aug - Mon, 17 Aug
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
Multiple Airlines Logo
12:30 a.m. - 11:07 a.m.
YYC
-
MDW
9h 37m
1 stop
C$ 532Multiple Airlines
Sat, 4 Jul - Tue, 7 Jul
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
Multiple Airlines Logo
12:30 a.m. - 11:07 a.m.
YYC
-
MDW
9h 37m
1 stop
C$ 533Multiple Airlines
Sat, 4 Jul - Tue, 7 Jul
Multiple Airlines Logo
6:00 a.m. - 9:50 p.m.
MDW
-
YYC
16h 50m
1 stop
Multiple Airlines Logo
12:30 a.m. - 11:07 a.m.
YYC
-
MDW
9h 37m
1 stop
C$ 540Multiple Airlines
Tue, 30 Jun - Tue, 7 Jul

Delta flights from Chicago Midway Airport to Calgary

Our best Delta deals on Chicago Midway Airport to Calgary flight tickets
Delta
24 Aug
MDW1:52 p.m.Chicago Midway
7h 43m
1 stop
YYC8:35 p.m.Calgary
28 Aug
YYC6:45 a.m.Calgary
5h 23m
1 stop
MDW1:08 p.m.Chicago Midway
C$ 458
Delta
22 Aug
MDW9:59 a.m.Chicago Midway
14h 10m
2 stops
YYC11:09 p.m.Calgary
28 Aug
YYC6:45 a.m.Calgary
5h 23m
1 stop
MDW1:08 p.m.Chicago Midway
C$ 470
Delta
26 Sep
MDW9:30 a.m.Chicago Midway
12h 14m
2 stops
YYC8:44 p.m.Calgary
3 Oct
YYC6:35 a.m.Calgary
5h 36m
1 stop
MDW1:11 p.m.Chicago Midway
C$ 477

Porter Airlines flights from Chicago Midway Airport to Calgary

Our best Porter Airlines deals on Chicago Midway Airport to Calgary flight tickets
Porter Airlines
27 May
MDW10:30 a.m.Chicago Midway
12h 50m
1 stop
YYC10:20 p.m.Calgary
1 Jun
YYC12:00 p.m.Calgary
20h 35m
2 stops
MDW9:35 a.m.Chicago Midway
C$ 858
Porter Airlines
23 May
MDW10:30 a.m.Chicago Midway
12h 56m
2 stops
YYC10:26 p.m.Calgary
29 May
YYC7:00 a.m.Calgary
25h 45m
3 stops
MDW9:45 a.m.Chicago Midway
C$ 915
Porter Airlines
23 May
MDW10:30 a.m.Chicago Midway
12h 56m
2 stops
YYC10:26 p.m.Calgary
29 May
YYC12:00 p.m.Calgary
20h 45m
2 stops
MDW9:45 a.m.Chicago Midway
C$ 958

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 13 May 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

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/8

6:00 a.m.-9:50 p.m.

1 stop16h 50m

Calgary

Mon 17/8

12:30 a.m.-11:12 a.m.

1 stop9h 42m

C$ 462

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/8

6:00 a.m.-5:10 p.m.

1 stop12h 10m

Calgary

Tue 18/8

9:00 p.m.-10:11 p.m.

2 stops24h 11m

C$ 475

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 30/7

12:11 p.m.-5:10 p.m.

1 stop29h 59m

Calgary

Mon 3/8

12:30 a.m.-11:07 a.m.

1 stop9h 37m

C$ 493

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 30/7

12:11 p.m.-5:10 p.m.

1 stop29h 59m

Calgary

Wed 5/8

9:00 p.m.-11:07 a.m.

2 stops13h 07m

C$ 511
Quickest round-trip

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 30/6

12:27 p.m.-9:50 p.m.

1 stop10h 23m

Calgary

Tue 7/7

12:30 a.m.-11:07 a.m.

1 stop9h 37m

C$ 518

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/8

6:00 a.m.-5:10 p.m.

1 stop12h 10m

Calgary

Wed 19/8

7:00 a.m.-10:11 p.m.

1 stop14h 11m

C$ 525

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/8

6:00 a.m.-5:10 p.m.

1 stop12h 10m

Calgary

Mon 17/8

12:30 a.m.-11:12 a.m.

1 stop9h 42m

C$ 530

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 4/7

6:00 a.m.-5:10 p.m.

1 stop12h 10m

Calgary

Tue 7/7

12:30 a.m.-11:07 a.m.

1 stop9h 37m

C$ 532

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 4/7

6:00 a.m.-5:10 p.m.

1 stop12h 10m

Calgary

Tue 7/7

12:30 a.m.-11:07 a.m.

1 stop9h 37m

C$ 533

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 30/6

6:00 a.m.-9:50 p.m.

1 stop16h 50m

Calgary

Tue 7/7

12:30 a.m.-11:07 a.m.

1 stop9h 37m

C$ 540

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 Friday when prices can be found for as low as C$ 362. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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$ 588.

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 at noon. Our users have found flights to Calgary at noon for as low as C$ 253. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 399 on average. Flights to Calgary from Chicago Midway Airport in the afternoon 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

7h 31m

Direct flights

None
The fastest flight from Chicago Midway Airport to Calgary takes 7h 31m
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

Frequently asked questions about flying from Chicago Midway Airport to Calgary

  • 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 7h 31m, 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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