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Cheap flights from Chicago Midway Airport to Calgary from $99

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 1/11. 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

These are some of the best round-trip flight deals from Chicago Midway Airport to Calgary that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Calgary.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Calgary? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Calgary, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Calgary

Find recent round-trip train or bus tickets from Chicago Midway Airport to Calgary.

All round-trip flight deals to Calgary

The cheapest plane tickets to Calgary found on KAYAK recently.
1:26 pm - 8:53 pmMDW-YYC
8h 27m1 stop
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
$250Delta
Find Deal
Mon, Jan 20 - Fri, Jan 24
12:43 pm - 10:55 pmMDW-YYC
11h 12m1 stop
9:55 am - 7:06 pmYYC-MDW
8h 11m1 stop
Sun, Jan 19 - Wed, Jan 29
12:43 pm - 10:55 pmMDW-YYC
11h 12m1 stop
9:45 pm - 11:54 amYYC-MDW
13h 09m2 stops
Sun, Jan 19 - Thu, Jan 23
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
$259Delta
Find Deal
Wed, Jan 8 - Wed, Jan 15
12:43 pm - 10:55 pmMDW-YYC
11h 12m1 stop
12:30 am - 11:54 amYYC-MDW
10h 24m1 stop
Sun, Jan 19 - Thu, Jan 23
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
6:35 am - 6:14 pmYYC-MDW
10h 39m2 stops
$264Delta
Find Deal
Wed, Jan 8 - Tue, Jan 14
9:30 am - 10:30 amMDW-YYC
26h 00m3 stops
1:15 pm - 6:32 pmYYC-MDW
28h 17m2 stops
$573WestJet
Find Deal
Wed, Dec 4 - Wed, Dec 11
9:30 am - 9:06 amMDW-YYC
24h 36m2 stops
1:15 pm - 6:32 pmYYC-MDW
28h 17m2 stops
$577WestJet
Find Deal
Wed, Dec 4 - Wed, Dec 11
1:05 pm - 11:30 pmMDW-YYC
11h 25m1 stop
4:20 pm - 12:10 pmYYC-MDW
18h 50m1 stop
$615Porter Airlines
Find Deal
Fri, Jan 17 - Fri, Jan 24
11:25 am - 9:36 pmMDW-YYC
11h 11m2 stops
7:40 am - 11:10 amYYC-MDW
26h 30m2 stops
$622Porter Airlines
Find Deal
Thu, Dec 12 - Thu, Dec 19
11:19 am - 8:53 pmMDW-YYC
10h 34m1 stop
$99Delta
Find Deal
Sat, Jan 11
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
$104Delta
Find Deal
Sat, Jan 11
4:06 pm - 11:50 pmMDW-YYC
8h 44m1 stop
Tue, Dec 17
9:30 am - 8:38 pmMDW-YYC
12h 08m2 stops
$127Delta
Find Deal
Wed, Dec 11
12:44 pm - 8:04 pmMDW-YYC
8h 20m1 stop
$140Delta
Find Deal
Tue, Feb 25
6:00 am - 3:16 pmMDW-YYC
34h 16m3 stops
Tue, Feb 25
9:30 am - 9:02 pmMDW-YYC
12h 32m2 stops
$184Delta
Find Deal
Tue, Mar 25
11:25 am - 11:33 pmMDW-YYC
13h 08m1 stop
$401Porter Airlines
Find Deal
Thu, Dec 26
12:43 pm - 8:04 pmMDW-YYC
8h 21m1 stop
$581WestJet
Find Deal
Sun, Dec 1
5:30 pm - 8:53 pmMDW-YYC
28h 23m1 stop
$594WestJet
Find Deal
Sun, Jan 5
9:00 am - 10:55 pmMDW-YYC
14h 55m2 stops
4:35 pm - 11:44 amYYC-MDW
18h 09m1 stop
Mon, Nov 25 - Wed, Nov 27
9:31 am - 8:35 pmMDW-YYC
12h 04m2 stops
7:00 am - 9:46 pmYYC-MDW
13h 46m2 stops
$595Delta
Find Deal
Mon, Nov 25 - Fri, Nov 29
9:00 am - 10:55 pmMDW-YYC
14h 55m2 stops
7:35 am - 9:26 pmYYC-MDW
12h 51m1 stop
Mon, Nov 25 - Fri, Nov 29
9:48 pm - 8:03 pmMDW-YYC
23h 15m2 stops
7:35 am - 9:26 pmYYC-MDW
12h 51m1 stop
Fri, Nov 22 - Fri, Nov 29
2:17 pm - 8:35 pmMDW-YYC
7h 18m1 stop
7:00 am - 1:35 pmYYC-MDW
5h 35m1 stop
$967WestJet
Find Deal
Mon, Nov 25 - Wed, Nov 27
11:15 am - 9:08 pmMDW-YYC
10h 53m2 stops
12:55 pm - 10:37 amYYC-MDW
20h 42m2 stops
$1,010
Find Deal
Mon, Nov 25 - Wed, Nov 27
7:17 pm - 1:50 pmMDW-YYC
19h 33m1 stop
7:00 am - 6:32 pmYYC-MDW
10h 32m1 stop
$1,064WestJet
Find Deal
Mon, Nov 25 - Fri, Nov 29
2:17 pm - 8:35 pmMDW-YYC
7h 18m1 stop
12:20 am - 5:54 pmYYC-MDW
16h 34m2 stops
$1,075WestJet
Find Deal
Mon, Nov 25 - Tue, Nov 26
12:43 pm - 1:06 amMDW-YYC
13h 23m2 stops
12:20 am - 5:54 pmYYC-MDW
16h 34m2 stops
$1,108WestJet
Find Deal
Mon, Nov 25 - Tue, Nov 26
9:30 am - 1:50 pmMDW-YYC
5h 20m1 stop
8:00 am - 9:46 pmYYC-MDW
12h 46m2 stops
$1,514Delta
Find Deal
Fri, Nov 22 - Sun, Nov 24

Delta flights from Chicago Midway Airport to Calgary

Our best Delta deals on Chicago Midway Airport to Calgary flight tickets
Delta
Jan 20
MDW1:26 pmChicago Midway
8h 27m
1 stop
YYC8:53 pmCalgary
Jan 24
YYC6:35 amCalgary
10h 12m
1 stop
MDW5:47 pmChicago Midway
Delta
Jan 8
MDW9:34 amChicago Midway
12h 19m
2 stops
YYC8:53 pmCalgary
Jan 15
YYC6:35 amCalgary
10h 12m
1 stop
MDW5:47 pmChicago Midway
Delta
Jan 8
MDW9:34 amChicago Midway
12h 19m
2 stops
YYC8:53 pmCalgary
Jan 14
YYC6:35 amCalgary
10h 39m
2 stops
MDW6:14 pmChicago Midway

WestJet flights from Chicago Midway Airport to Calgary

Our best WestJet deals on Chicago Midway Airport to Calgary flight tickets
WestJet
Dec 4
MDW9:30 amChicago Midway
26h 00m
3 stops
YYC10:30 amCalgary
Dec 11
YYC1:15 pmCalgary
28h 17m
2 stops
MDW6:32 pmChicago Midway
WestJet
Dec 4
MDW9:30 amChicago Midway
24h 36m
2 stops
YYC9:06 amCalgary
Dec 11
YYC1:15 pmCalgary
28h 17m
2 stops
MDW6:32 pmChicago Midway
WestJet
Jan 16
MDW10:19 amChicago Midway
25h 11m
2 stops
YYC10:30 amCalgary
Jan 20
YYC1:10 pmCalgary
27h 37m
2 stops
MDW5:47 pmChicago Midway

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 month to fly to Calgary?

The month of September is, on average, the cheapest month to fly to Calgary from Chicago Midway Airport, with most prices found around $284. If you aren’t able to travel during the month of September, then book flights to Calgary from Chicago Midway Airport during April instead. Flights to Calgary in April, while not as cheap as those in September, still average around $293.

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 $320. 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 Monday will generally be more expensive and average around $351. 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 $282. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are $389 on average. Flights to Calgary from Chicago Midway Airport in the evening are generally more expensive because this time of day is more convenient for travelers’ schedules.

How far in advance should I book a flight to Calgary?

Most flyers found that booking tickets 36 days in advance of their planned departure date is the best time to get cheap flights to Calgary. During this timeframe, flight prices are around $351. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $194.

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

You could potentially save up to 4% 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

Best Price Found

$99

Fastest flight time

5h 20m

Direct flights

None

Airports in Calgary

1 airport
The best one-way flight to Calgary from Chicago Midway Airport in the past 72 hours is $99. The best round-trip flight deal from Chicago Midway Airport to Calgary found on momondo in the last 72 hours is $250.
The fastest flight from Chicago Midway Airport to Calgary takes 5h 20m
There are no direct flights from Chicago Midway Airport to Calgary. Popular non-direct route for this connection is Chicago Midway Airport - Calgary Airport.
There is 1 airport near Calgary: Calgary (YYC)

  • 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.


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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