Cheap flights from Chicago Midway Airport to Calgary from $100

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 9/30. 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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Find the cheapest flights from Chicago Midway Airport to Calgary

Cheap round-trip flights

Delta Logo
1:43 pm - 8:42 pmMDW-YYC
7h 59m1 stop
Delta Logo
6:40 am - 5:35 pmYYC-MDW
9h 55m1 stop
$251Delta
Find Deal
Tue, Sep 30 - Fri, Oct 3
Multiple Airlines Logo
6:30 am - 5:06 pmMDW-YYC
11h 36m1 stop
Multiple Airlines Logo
8:15 pm - 11:38 amYYC-MDW
14h 23m2 stops
$254Multiple Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3
Multiple Airlines Logo
8:05 am - 8:00 pmMDW-YYC
12h 55m1 stop
Multiple Airlines Logo
12:30 am - 1:38 pmYYC-MDW
12h 08m1 stop
$256Multiple Airlines
Find Deal
Tue, Oct 21 - Tue, Oct 21
Multiple Airlines Logo
6:30 am - 5:06 pmMDW-YYC
11h 36m1 stop
Multiple Airlines Logo
8:55 am - 12:41 pmYYC-MDW
26h 46m1 stop
$258Multiple Airlines
Find Deal
Thu, Nov 6 - Tue, Nov 11
Multiple Airlines Logo
10:00 am - 6:21 pmMDW-YYC
9h 21m1 stop
Multiple Airlines Logo
7:00 am - 11:46 pmYYC-MDW
15h 46m2 stops
$259Multiple Airlines
Find Deal
Sat, Oct 18 - Fri, Oct 24
Delta Logo
9:20 am - 1:54 pmMDW-YYC
5h 34m1 stop
Delta Logo
6:20 am - 6:08 pmYYC-MDW
10h 48m2 stops
$261Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
Delta Logo
9:20 am - 1:54 pmMDW-YYC
5h 34m1 stop
Delta Logo
6:20 am - 1:07 pmYYC-MDW
5h 47m1 stop
$262Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
Delta Logo
11:10 am - 8:47 pmMDW-YYC
10h 37m2 stops
Delta Logo
7:45 am - 6:18 pmYYC-MDW
9h 33m2 stops
$266Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
Multiple Airlines Logo
6:30 am - 5:06 pmMDW-YYC
11h 36m1 stop
Multiple Airlines Logo
11:30 pm - 6:39 pmYYC-MDW
42h 09m2 stops
$270Multiple Airlines
Find Deal
Thu, Nov 6 - Tue, Nov 11
Delta Logo
3:00 pm - 8:47 pmMDW-YYC
6h 47m1 stop
Delta Logo
6:20 am - 6:08 pmYYC-MDW
10h 48m2 stops
$271Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15

Delta flights from Chicago Midway Airport to Calgary

Our best Delta deals on Chicago Midway Airport to Calgary flight tickets
Delta
Sep 30
MDW1:43 pmChicago Midway
7h 59m
1 stop
YYC8:42 pmCalgary
Oct 3
YYC6:40 amCalgary
9h 55m
1 stop
MDW5:35 pmChicago Midway
Delta
Nov 8
MDW9:20 amChicago Midway
5h 34m
1 stop
YYC1:54 pmCalgary
Nov 15
YYC6:20 amCalgary
10h 48m
2 stops
MDW6:08 pmChicago Midway
Delta
Nov 8
MDW9:20 amChicago Midway
5h 34m
1 stop
YYC1:54 pmCalgary
Nov 15
YYC6:20 amCalgary
5h 47m
1 stop
MDW1:07 pmChicago Midway

WestJet flights from Chicago Midway Airport to Calgary

Our best WestJet deals on Chicago Midway Airport to Calgary flight tickets
WestJet
Sep 28
MDW7:15 pmChicago Midway
30h 29m
2 stops
YYC12:44 amCalgary
Oct 1
YYC6:00 amCalgary
10h 35m
2 stops
MDW5:35 pmChicago Midway
WestJet
Sep 30
MDW9:20 amChicago Midway
24h 30m
2 stops
YYC8:50 amCalgary
Oct 7
YYC6:30 pmCalgary
17h 38m
2 stops
MDW1:08 pmChicago Midway
WestJet
Sep 28
MDW9:20 amChicago Midway
25h 24m
2 stops
YYC9:44 amCalgary
Sep 29
YYC9:30 pmCalgary
14h 33m
2 stops
MDW1:03 pmChicago Midway

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 September 17, 2025.
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

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 9/30

1:43 pm-8:42 pm

1 stop7h 59m

Calgary

Fri 10/3

6:40 am-5:35 pm

1 stop9h 55m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 10/30

6:30 am-5:06 pm

1 stop11h 36m

Calgary

Mon 11/3

8:15 pm-11:38 am

2 stops14h 23m

$254

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 10/21

8:05 am-8:00 pm

1 stop12h 55m

Calgary

Tue 10/21

12:30 am-1:38 pm

1 stop12h 08m

$256

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 11/6

6:30 am-5:06 pm

1 stop11h 36m

Calgary

Tue 11/11

8:55 am-12:41 pm

1 stop26h 46m

$258

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 10/18

10:00 am-6:21 pm

1 stop9h 21m

Calgary

Fri 10/24

7:00 am-11:46 pm

2 stops15h 46m

$259

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

9:20 am-1:54 pm

1 stop5h 34m

Calgary

Sat 11/15

6:20 am-6:08 pm

2 stops10h 48m

$261

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

9:20 am-1:54 pm

1 stop5h 34m

Calgary

Sat 11/15

6:20 am-1:07 pm

1 stop5h 47m

$262

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

11:10 am-8:47 pm

2 stops10h 37m

Calgary

Sat 11/15

7:45 am-6:18 pm

2 stops9h 33m

$266

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 11/6

6:30 am-5:06 pm

1 stop11h 36m

Calgary

Tue 11/11

11:30 pm-6:39 pm

2 stops42h 09m

$270

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

3:00 pm-8:47 pm

1 stop6h 47m

Calgary

Sat 11/15

6:20 am-6:08 pm

2 stops10h 48m

$271

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 $291. 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 Tuesday will generally be more expensive and average around $332. 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 $204. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $471 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

Direct flights

None
There are no direct flights from Chicago Midway Airport to Calgary. There are no popular flight routes 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 34m, 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
Radium Hot Springs
Drumheller
Kananaskis
Airdrie

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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1 adult
Fri 10/17
Fri 10/24

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