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Cheap flights from Chicago Midway Airport to Calgary from $133

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 4/28. 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
9:27 am - 8:40 pm
MDW
-
YYC
12h 13m
2 stops
Delta Logo
6:45 am - 1:19 pm
YYC
-
MDW
5h 34m
1 stop
$311Delta
Wed, May 6 - Tue, May 12
Delta Logo
9:27 am - 8:40 pm
MDW
-
YYC
12h 13m
2 stops
Delta Logo
6:45 am - 6:33 pm
YYC
-
MDW
10h 48m
2 stops
$320Delta
Wed, May 6 - Wed, May 13
Multiple Airlines Logo
12:04 pm - 11:00 am
MDW
-
YYC
23h 56m
1 stop
Multiple Airlines Logo
12:30 am - 11:09 am
YYC
-
MDW
9h 39m
1 stop
$323Multiple Airlines
Wed, May 6 - Mon, May 11
Delta Logo
9:22 am - 8:30 pm
MDW
-
YYC
12h 08m
2 stops
Delta Logo
6:45 am - 1:19 pm
YYC
-
MDW
5h 34m
1 stop
$332Delta
Sat, May 9 - Sat, May 16
Multiple Airlines Logo
2:15 pm - 11:00 am
MDW
-
YYC
21h 45m
1 stop
Multiple Airlines Logo
7:00 am - 7:31 pm
YYC
-
MDW
11h 31m
1 stop
$339Multiple Airlines
Mon, Apr 27 - Thu, Apr 30
Delta Logo
1:59 pm - 8:30 pm
MDW
-
YYC
7h 31m
1 stop
Delta Logo
6:45 am - 1:19 pm
YYC
-
MDW
5h 34m
1 stop
$342Delta
Sat, May 9 - Sat, May 16
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
$343Delta
Wed, Oct 7 - Sat, Oct 10
Delta Logo
12:30 pm - 11:13 pm
MDW
-
YYC
11h 43m
2 stops
Delta Logo
7:45 am - 9:45 pm
YYC
-
MDW
13h 00m
2 stops
$348Delta
Wed, Oct 7 - Sat, Oct 10
Delta Logo
1:22 pm - 8:05 pm
MDW
-
YYC
7h 43m
1 stop
Delta Logo
12:30 am - 9:59 am
YYC
-
MDW
8h 29m
1 stop
$352Delta
Wed, May 27 - Fri, May 29
Multiple Airlines Logo
12:24 pm - 11:00 am
MDW
-
YYC
23h 36m
1 stop
Multiple Airlines Logo
11:35 pm - 10:02 pm
YYC
-
MDW
21h 27m
2 stops
$353Multiple Airlines
Tue, May 5 - Fri, May 8

Delta flights from Chicago Midway Airport to Calgary

Our best Delta deals on Chicago Midway Airport to Calgary flight tickets
Delta
May 6
MDW9:27 amChicago Midway
12h 13m
2 stops
YYC8:40 pmCalgary
May 12
YYC6:45 amCalgary
5h 34m
1 stop
MDW1:19 pmChicago Midway
$311
Delta
May 6
MDW9:27 amChicago Midway
12h 13m
2 stops
YYC8:40 pmCalgary
May 13
YYC6:45 amCalgary
10h 48m
2 stops
MDW6:33 pmChicago Midway
$320
Delta
Oct 7
MDW12:30 pmChicago Midway
9h 24m
1 stop
YYC8:54 pmCalgary
Oct 10
YYC7:45 amCalgary
13h 00m
2 stops
MDW9:45 pmChicago Midway
$343

WestJet flights from Chicago Midway Airport to Calgary

Our best WestJet deals on Chicago Midway Airport to Calgary flight tickets
WestJet
Apr 20
MDW10:41 amChicago Midway
26h 02m
1 stop
YYC11:43 amCalgary
Apr 21
YYC6:30 pmCalgary
13h 17m
2 stops
MDW8:47 amChicago Midway
$862
WestJet
Apr 24
MDW7:16 pmChicago Midway
26h 24m
1 stop
YYC8:40 pmCalgary
Apr 29
YYC6:40 amCalgary
5h 52m
1 stop
MDW1:32 pmChicago Midway
$903
WestJet
Apr 16
MDW9:27 amChicago Midway
12h 31m
2 stops
YYC8:58 pmCalgary
Apr 23
YYC6:30 pmCalgary
13h 17m
2 stops
MDW8:47 amChicago Midway
$946

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 April 14, 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

Wed 5/6

9:27 am-8:40 pm

2 stops12h 13m

Calgary

Tue 5/12

6:45 am-1:19 pm

1 stop5h 34m

$311

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 5/6

9:27 am-8:40 pm

2 stops12h 13m

Calgary

Wed 5/13

6:45 am-6:33 pm

2 stops10h 48m

$320

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 5/6

12:04 pm-11:00 am

1 stop23h 56m

Calgary

Mon 5/11

12:30 am-11:09 am

1 stop9h 39m

$323

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/9

9:22 am-8:30 pm

2 stops12h 08m

Calgary

Sat 5/16

6:45 am-1:19 pm

1 stop5h 34m

$332

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 4/27

2:15 pm-11:00 am

1 stop21h 45m

Calgary

Thu 4/30

7:00 am-7:31 pm

1 stop11h 31m

$339
Quickest round-trip

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 5/9

1:59 pm-8:30 pm

1 stop7h 31m

Calgary

Sat 5/16

6:45 am-1:19 pm

1 stop5h 34m

$342

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/7

12:30 pm-8:54 pm

1 stop9h 24m

Calgary

Sat 10/10

7:45 am-9:45 pm

2 stops13h 00m

$343

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/7

12:30 pm-11:13 pm

2 stops11h 43m

Calgary

Sat 10/10

7:45 am-9:45 pm

2 stops13h 00m

$348

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 5/27

1:22 pm-8:05 pm

1 stop7h 43m

Calgary

Fri 5/29

12:30 am-9:59 am

1 stop8h 29m

$352

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 5/5

12:24 pm-11:00 am

1 stop23h 36m

Calgary

Fri 5/8

11:35 pm-10:02 pm

2 stops21h 27m

$353

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 Monday when prices can be found for as low as $293. 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 Saturday will generally be more expensive and average around $345. 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 $274. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $447 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

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

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 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 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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