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Cheap flights from Chicago Midway Airport to Calgary from $127

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 10/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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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
1:52 pm - 8:35 pm
MDW
-
YYC
7h 43m
1 stop
Delta Logo
6:45 am - 1:08 pm
YYC
-
MDW
5h 23m
1 stop
$334Delta
Mon, Aug 24 - Fri, Aug 28
Delta Logo
9:59 am - 11:09 pm
MDW
-
YYC
14h 10m
2 stops
Delta Logo
6:45 am - 1:08 pm
YYC
-
MDW
5h 23m
1 stop
$343Delta
Sat, Aug 22 - Fri, Aug 28
Delta Logo
9:30 am - 8:44 pm
MDW
-
YYC
12h 14m
2 stops
Delta Logo
6:35 am - 1:11 pm
YYC
-
MDW
5h 36m
1 stop
$348Delta
Sat, Sep 26 - Sat, Oct 3
Delta Logo
12:30 pm - 11:13 pm
MDW
-
YYC
11h 43m
2 stops
Delta Logo
7:45 am - 6:37 pm
YYC
-
MDW
9h 52m
2 stops
$349Delta
Sat, Oct 17 - Sat, Oct 24
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
$350Delta
Mon, Oct 19 - Fri, Oct 30
Delta Logo
9:22 am - 8:30 pm
MDW
-
YYC
12h 08m
2 stops
Delta Logo
6:45 am - 5:56 pm
YYC
-
MDW
10h 11m
1 stop
$355Delta
Thu, May 28 - Sun, May 31
Delta Logo
12:30 pm - 8:54 pm
MDW
-
YYC
9h 24m
1 stop
Delta Logo
7:45 am - 9:45 pm
YYC
-
MDW
13h 00m
2 stops
$360Delta
Tue, Nov 3 - Tue, Nov 10
Multiple Airlines Logo
12:11 pm - 11:00 am
MDW
-
YYC
23h 49m
1 stop
Multiple Airlines Logo
12:30 am - 11:12 am
YYC
-
MDW
9h 42m
1 stop
$364Multiple Airlines
Sat, Aug 15 - Mon, Aug 17
Delta Logo
9:30 am - 8:54 pm
MDW
-
YYC
12h 24m
2 stops
Delta Logo
7:45 am - 9:45 pm
YYC
-
MDW
13h 00m
2 stops
$365Delta
Tue, Nov 3 - Tue, Nov 10
Multiple Airlines Logo
12:11 pm - 5:10 pm
MDW
-
YYC
29h 59m
1 stop
Multiple Airlines Logo
9:00 pm - 11:07 am
YYC
-
MDW
13h 07m
2 stops
$373Multiple Airlines
Thu, Jul 30 - Wed, Aug 5

Delta flights from Chicago Midway Airport to Calgary

Our best Delta deals on Chicago Midway Airport to Calgary flight tickets
Delta
Aug 24
MDW1:52 pmChicago Midway
7h 43m
1 stop
YYC8:35 pmCalgary
Aug 28
YYC6:45 amCalgary
5h 23m
1 stop
MDW1:08 pmChicago Midway
$334
Delta
Aug 22
MDW9:59 amChicago Midway
14h 10m
2 stops
YYC11:09 pmCalgary
Aug 28
YYC6:45 amCalgary
5h 23m
1 stop
MDW1:08 pmChicago Midway
$343
Delta
Sep 26
MDW9:30 amChicago Midway
12h 14m
2 stops
YYC8:44 pmCalgary
Oct 3
YYC6:35 amCalgary
5h 36m
1 stop
MDW1:11 pmChicago Midway
$348

WestJet flights from Chicago Midway Airport to Calgary

Our best WestJet deals on Chicago Midway Airport to Calgary flight tickets
WestJet
May 24
MDW9:22 amChicago Midway
9h 48m
2 stops
YYC6:10 pmCalgary
May 25
YYC7:00 amCalgary
8h 12m
1 stop
MDW4:12 pmChicago Midway
$632
WestJet
May 24
MDW9:23 amChicago Midway
8h 37m
1 stop
YYC5:00 pmCalgary
May 28
YYC6:45 amCalgary
5h 34m
1 stop
MDW1:19 pmChicago Midway
$951
WestJet
May 22
MDW9:22 amChicago Midway
11h 43m
1 stop
YYC8:05 pmCalgary
May 31
YYC1:00 amCalgary
10h 42m
2 stops
MDW12:42 pmChicago Midway
$960

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 May 12, 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

Mon 8/24

1:52 pm-8:35 pm

1 stop7h 43m

Calgary

Fri 8/28

6:45 am-1:08 pm

1 stop5h 23m

$334

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 8/22

9:59 am-11:09 pm

2 stops14h 10m

Calgary

Fri 8/28

6:45 am-1:08 pm

1 stop5h 23m

$343

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 9/26

9:30 am-8:44 pm

2 stops12h 14m

Calgary

Sat 10/3

6:35 am-1:11 pm

1 stop5h 36m

$348

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 10/17

12:30 pm-11:13 pm

2 stops11h 43m

Calgary

Sat 10/24

7:45 am-6:37 pm

2 stops9h 52m

$349

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 10/19

12:30 pm-8:54 pm

1 stop9h 24m

Calgary

Fri 10/30

7:45 am-4:50 pm

1 stop8h 05m

$350

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 5/28

9:22 am-8:30 pm

2 stops12h 08m

Calgary

Sun 5/31

6:45 am-5:56 pm

1 stop10h 11m

$355

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/3

12:30 pm-8:54 pm

1 stop9h 24m

Calgary

Tue 11/10

7:45 am-9:45 pm

2 stops13h 00m

$360

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 8/15

12:11 pm-11:00 am

1 stop23h 49m

Calgary

Mon 8/17

12:30 am-11:12 am

1 stop9h 42m

$364

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 11/3

9:30 am-8:54 pm

2 stops12h 24m

Calgary

Tue 11/10

7:45 am-9:45 pm

2 stops13h 00m

$365

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 7/30

12:11 pm-5:10 pm

1 stop29h 59m

Calgary

Wed 8/5

9:00 pm-11:07 am

2 stops13h 07m

$373

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 $313. 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 Wednesday will generally be more expensive and average around $352. 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 in the afternoon when flights can be purchased for as low as $281. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $457 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.

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?

    There are 1396.3 mi between Chicago Midway and Calgary. 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 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
Drumheller
Kananaskis

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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