Cheap flights from Chicago Midway Airport to Calgary from $94

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 10/7. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from Chicago Midway Airport to Calgary

Cheap round-trip flights

 Logo
8:05 am - 12:44 amMDW-YYC
17h 39m2 stops
 Logo
5:30 pm - 4:09 pmYYC-MDW
21h 39m1 stop
Wed, Oct 22 - Fri, Oct 24
 Logo
8:05 am - 8:00 pmMDW-YYC
12h 55m1 stop
 Logo
5:30 pm - 4:09 pmYYC-MDW
21h 39m1 stop
Wed, Oct 22 - Fri, Oct 24
 Logo
10:00 am - 6:21 pmMDW-YYC
9h 21m1 stop
 Logo
12:30 am - 1:38 pmYYC-MDW
12h 08m1 stop
Sat, Oct 11 - Tue, Oct 14
 Logo
6:20 am - 8:00 pmMDW-YYC
14h 40m1 stop
 Logo
12:30 am - 1:38 pmYYC-MDW
12h 08m1 stop
Mon, Oct 6 - Tue, Oct 14
 Logo
8:05 am - 12:44 amMDW-YYC
17h 39m2 stops
 Logo
5:30 pm - 4:09 pmYYC-MDW
21h 39m1 stop
Wed, Oct 22 - Fri, Oct 24
 Logo
8:05 am - 12:44 amMDW-YYC
17h 39m2 stops
 Logo
5:30 pm - 4:09 pmYYC-MDW
21h 39m1 stop
Wed, Oct 15 - Fri, Oct 17
 Logo
8:05 am - 8:00 pmMDW-YYC
12h 55m1 stop
 Logo
10:00 am - 11:46 pmYYC-MDW
12h 46m1 stop
Wed, Oct 22 - Fri, Oct 24
Delta Logo
9:20 am - 1:54 pmMDW-YYC
5h 34m1 stop
Delta Logo
6:45 am - 5:43 pmYYC-MDW
9h 58m1 stop
$251Delta
Find Deal
Tue, Oct 7 - Sat, Oct 11
 Logo
10:56 pm - 12:12 pmMDW-YYC
14h 16m1 stop
 Logo
12:30 am - 1:38 pmYYC-MDW
12h 08m1 stop
Mon, Oct 20 - Tue, Oct 21
Delta Logo
11:10 am - 11:02 pmMDW-YYC
12h 52m2 stops
Delta Logo
6:20 am - 1:07 pmYYC-MDW
5h 47m1 stop
$261Delta
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
Oct 7
MDW9:20 amChicago Midway
5h 34m
1 stop
YYC1:54 pmCalgary
Oct 11
YYC6:45 amCalgary
9h 58m
1 stop
MDW5:43 pmChicago Midway
Delta
Nov 8
MDW11:10 amChicago Midway
12h 52m
2 stops
YYC11:02 pmCalgary
Nov 15
YYC6:20 amCalgary
5h 47m
1 stop
MDW1:07 pmChicago Midway
Delta
Nov 8
MDW11:10 amChicago Midway
12h 52m
2 stops
YYC11:02 pmCalgary
Nov 15
YYC6:20 amCalgary
10h 48m
2 stops
MDW6:08 pmChicago Midway

WestJet flights from Chicago Midway Airport to Calgary

Our best WestJet deals on Chicago Midway Airport to Calgary flight tickets
WestJet
Sep 17
MDW12:43 pmChicago Midway
8h 17m
1 stop
YYC8:00 pmCalgary
Sep 19
YYC12:30 amCalgary
8h 17m
1 stop
MDW9:47 amChicago Midway
WestJet
Sep 17
MDW12:43 pmChicago Midway
28h 07m
2 stops
YYC3:50 pmCalgary
Sep 19
YYC12:30 amCalgary
8h 17m
1 stop
MDW9:47 amChicago Midway
WestJet
Sep 18
MDW12:43 pmChicago Midway
34h 35m
2 stops
YYC10:18 pmCalgary
Sep 21
YYC12:20 amCalgary
20h 16m
2 stops
MDW9:36 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 11, 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

Wed 10/22

8:05 am-12:44 am

2 stops17h 39m

Calgary

Fri 10/24

5:30 pm-4:09 pm

1 stop21h 39m

$224

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/22

8:05 am-8:00 pm

1 stop12h 55m

Calgary

Fri 10/24

5:30 pm-4:09 pm

1 stop21h 39m

$234

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 10/11

10:00 am-6:21 pm

1 stop9h 21m

Calgary

Tue 10/14

12:30 am-1:38 pm

1 stop12h 08m

$235

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 10/6

6:20 am-8:00 pm

1 stop14h 40m

Calgary

Tue 10/14

12:30 am-1:38 pm

1 stop12h 08m

$237

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/22

8:05 am-12:44 am

2 stops17h 39m

Calgary

Fri 10/24

5:30 pm-4:09 pm

1 stop21h 39m

$242

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/15

8:05 am-12:44 am

2 stops17h 39m

Calgary

Fri 10/17

5:30 pm-4:09 pm

1 stop21h 39m

$245

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 10/22

8:05 am-8:00 pm

1 stop12h 55m

Calgary

Fri 10/24

10:00 am-11:46 pm

1 stop12h 46m

$248

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 10/7

9:20 am-1:54 pm

1 stop5h 34m

Calgary

Sat 10/11

6:45 am-5:43 pm

1 stop9h 58m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 10/20

10:56 pm-12:12 pm

1 stop14h 16m

Calgary

Tue 10/21

12:30 am-1:38 pm

1 stop12h 08m

$252

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 11/8

11:10 am-11:02 pm

2 stops12h 52m

Calgary

Sat 11/15

6:20 am-1:07 pm

1 stop5h 47m

$261

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $334. 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 $265. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $476 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
Airdrie
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.

An easier way to manage your Calgary trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 10/11
Sat 10/18

Find better results for your trip to Canada