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Cheap flights from Chicago Midway Airport to Calgary from $147

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 12/18. 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
1 adult, Economy, 0 bags

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
12:28 pm - 8:30 pm
MDW
-
YYC
9h 02m
1 stop
Delta Logo
7:45 am - 10:10 pm
YYC
-
MDW
13h 25m
2 stops
$315Delta
Tue, Nov 3 - Mon, Nov 9
Delta Logo
12:28 pm - 11:04 pm
MDW
-
YYC
11h 36m
2 stops
Delta Logo
7:45 am - 10:10 pm
YYC
-
MDW
13h 25m
2 stops
$320Delta
Tue, Nov 3 - Mon, Nov 9
Delta Logo
12:28 pm - 8:30 pm
MDW
-
YYC
9h 02m
1 stop
Delta Logo
7:45 am - 10:10 pm
YYC
-
MDW
13h 25m
2 stops
$324Delta
Tue, Nov 3 - Mon, Nov 9
Delta Logo
9:29 am - 8:30 pm
MDW
-
YYC
12h 01m
2 stops
Delta Logo
7:45 am - 10:10 pm
YYC
-
MDW
13h 25m
2 stops
$330Delta
Tue, Nov 3 - Mon, Nov 9
Delta Logo
2:00 pm - 8:42 pm
MDW
-
YYC
7h 42m
1 stop
Delta Logo
6:35 am - 1:20 pm
YYC
-
MDW
5h 45m
1 stop
$340Delta
Thu, Sep 24 - Wed, Sep 30
Delta Logo
12:28 pm - 8:30 pm
MDW
-
YYC
9h 02m
1 stop
Delta Logo
7:45 am - 10:10 pm
YYC
-
MDW
13h 25m
2 stops
$355Delta
Tue, Nov 3 - Mon, Nov 9
Delta Logo
12:30 pm - 8:54 pm
MDW
-
YYC
9h 24m
1 stop
Delta Logo
7:45 am - 4:50 pm
YYC
-
MDW
8h 05m
1 stop
$358Delta
Fri, Nov 13 - Tue, Nov 17
Delta Logo
12:28 pm - 11:04 pm
MDW
-
YYC
11h 36m
2 stops
Delta Logo
7:45 am - 10:10 pm
YYC
-
MDW
13h 25m
2 stops
$360Delta
Tue, Nov 3 - Mon, Nov 9
Multiple Airlines Logo
11:50 am - 9:50 pm
MDW
-
YYC
11h 00m
1 stop
Multiple Airlines Logo
12:20 am - 10:58 am
YYC
-
MDW
9h 38m
1 stop
$368Multiple Airlines
Tue, Sep 1 - Thu, Sep 10
Multiple Airlines Logo
6:05 am - 9:50 pm
MDW
-
YYC
16h 45m
1 stop
Multiple Airlines Logo
12:20 am - 10:55 am
YYC
-
MDW
9h 35m
1 stop
$370Multiple Airlines
Mon, Aug 24 - Wed, Aug 26

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Delta flights from Chicago Midway Airport to Calgary

Our best Delta deals on Chicago Midway Airport to Calgary flight tickets
Delta
Nov 3
MDW12:28 pmChicago Midway
9h 02m
1 stop
YYC8:30 pmCalgary
Nov 9
YYC7:45 amCalgary
13h 25m
2 stops
MDW10:10 pmChicago Midway
$315
Delta
Nov 3
MDW12:28 pmChicago Midway
11h 36m
2 stops
YYC11:04 pmCalgary
Nov 9
YYC7:45 amCalgary
13h 25m
2 stops
MDW10:10 pmChicago Midway
$320
Delta
Nov 3
MDW12:28 pmChicago Midway
9h 02m
1 stop
YYC8:30 pmCalgary
Nov 9
YYC7:45 amCalgary
13h 25m
2 stops
MDW10:10 pmChicago Midway
$324

Porter Airlines flights from Chicago Midway Airport to Calgary

Our best Porter Airlines deals on Chicago Midway Airport to Calgary flight tickets
Porter Airlines
Jul 20
MDW10:25 amChicago Midway
13h 08m
2 stops
YYC10:33 pmCalgary
Jul 26
YYC11:55 pmCalgary
13h 40m
1 stop
MDW2:35 pmChicago Midway
$728
Porter Airlines
Jul 22
MDW10:25 amChicago Midway
13h 08m
2 stops
YYC10:33 pmCalgary
Jul 24
YYC12:00 pmCalgary
20h 40m
2 stops
MDW9:40 amChicago Midway
$757
Porter Airlines
Jul 22
MDW10:25 amChicago Midway
13h 08m
2 stops
YYC10:33 pmCalgary
Jul 29
YYC12:00 pmCalgary
20h 40m
2 stops
MDW9:40 amChicago Midway
$778

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 832,500 searches. Data last updated July 10, 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 11/3

12:28 pm-8:30 pm

1 stop9h 02m

Calgary

Mon 11/9

7:45 am-10:10 pm

2 stops13h 25m

$315

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/3

12:28 pm-11:04 pm

2 stops11h 36m

Calgary

Mon 11/9

7:45 am-10:10 pm

2 stops13h 25m

$320

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/3

12:28 pm-8:30 pm

1 stop9h 02m

Calgary

Mon 11/9

7:45 am-10:10 pm

2 stops13h 25m

$324

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/3

9:29 am-8:30 pm

2 stops12h 01m

Calgary

Mon 11/9

7:45 am-10:10 pm

2 stops13h 25m

$330
Quickest round-trip

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 9/24

2:00 pm-8:42 pm

1 stop7h 42m

Calgary

Wed 9/30

6:35 am-1:20 pm

1 stop5h 45m

$340

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/3

12:28 pm-8:30 pm

1 stop9h 02m

Calgary

Mon 11/9

7:45 am-10:10 pm

2 stops13h 25m

$355

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 11/13

12:30 pm-8:54 pm

1 stop9h 24m

Calgary

Tue 11/17

7:45 am-4:50 pm

1 stop8h 05m

$358

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/3

12:28 pm-11:04 pm

2 stops11h 36m

Calgary

Mon 11/9

7:45 am-10:10 pm

2 stops13h 25m

$360

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 9/1

11:50 am-9:50 pm

1 stop11h 00m

Calgary

Thu 9/10

12:20 am-10:58 am

1 stop9h 38m

$368

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 8/24

6:05 am-9:50 pm

1 stop16h 45m

Calgary

Wed 8/26

12:20 am-10:55 am

1 stop9h 35m

$370

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 $346. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago Midway Airport to Calgary on a Thursday will generally be more expensive and average around $388. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

The cheapest time of day to fly to Calgary is at noon when flights can be purchased for as low as $283. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $478 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 travelers’ schedules.

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

You could potentially save up to 37% 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 44m

Direct flights

None
The fastest flight from Chicago Midway Airport to Calgary takes 7h 44m
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?

    There are 1396.3 mi between Chicago Midway and Calgary. Flights usually cover this in 7h 44m, 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 are refreshed on a daily basis.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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.

Traveling to a place near Calgary?

Book flights to Calgary if you plan to visit one of these locations
Banff
Canmore
Lake Louise
Airdrie
Radium Hot Springs
Kananaskis
Drumheller

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Calgary. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Calgary from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Chicago and Calgary by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Calgary from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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