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Cheap flights from Calgary to Chicago Midway Airport from $136

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Calgary to Chicago Midway Airport departing on 12/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Calgary to Chicago 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 Calgary to Chicago.

Cheap last minute flights

Planning a quick getaway from Calgary to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Calgary to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
$221Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
$252Delta
Find Deal
Mon, Jan 27 - Thu, Jan 30
7:45 am - 6:11 pmYYC-MDW
9h 26m1 stop
10:10 am - 8:04 pmMDW-YYC
10h 54m1 stop
$303Delta
Find Deal
Thu, Feb 13 - Wed, Feb 19
12:20 pm - 10:45 pmYYC-MDW
9h 25m1 stop
6:17 pm - 3:16 pmMDW-YYC
21h 59m2 stops
Thu, Dec 5 - Mon, Dec 9
12:30 am - 5:12 pmYYC-MDW
15h 42m1 stop
12:55 pm - 9:36 pmMDW-YYC
9h 41m2 stops
Thu, Dec 5 - Sat, Dec 7
6:00 am - 6:32 pmYYC-MDW
11h 32m2 stops
10:38 am - 11:16 pmMDW-YYC
13h 38m2 stops
$407Delta
Find Deal
Fri, Dec 13 - Sun, Dec 15
4:25 pm - 10:20 amYYC-MDW
16h 55m1 stop
12:55 pm - 9:36 pmMDW-YYC
9h 41m2 stops
$434Porter Airlines
Find Deal
Thu, Nov 28 - Sat, Dec 7
7:10 am - 10:20 amYYC-MDW
26h 10m1 stop
11:15 am - 3:28 pmMDW-YYC
29h 13m1 stop
$467Porter Airlines
Find Deal
Thu, Nov 28 - Sun, Dec 8
3:00 pm - 6:32 pmYYC-MDW
26h 32m1 stop
9:30 am - 8:35 pmMDW-YYC
12h 05m1 stop
$495WestJet
Find Deal
Mon, Nov 25 - Fri, Nov 29
9:45 pm - 9:32 amYYC-MDW
10h 47m2 stops
9:30 am - 7:08 pmMDW-YYC
10h 38m2 stops
$508WestJet
Find Deal
Mon, Nov 25 - Fri, Nov 29
8:00 am - 10:06 pmYYC-MDW
13h 06m2 stops
$136Delta
Find Deal
Sat, Dec 7
7:00 am - 6:32 pmYYC-MDW
10h 32m1 stop
$137Delta
Find Deal
Thu, Dec 12
9:55 am - 11:29 pmYYC-MDW
12h 34m1 stop
Sat, Dec 7
7:00 am - 6:32 pmYYC-MDW
10h 32m2 stops
$161Delta
Find Deal
Thu, Dec 12
7:10 pm - 10:45 pmYYC-MDW
26h 35m2 stops
Wed, Dec 4
9:45 pm - 12:20 amYYC-MDW
25h 35m3 stops
Thu, Dec 12
11:30 pm - 12:13 amYYC-MDW
23h 43m3 stops
Wed, Dec 4
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
$276WestJet
Find Deal
Fri, Feb 7
8:15 pm - 10:12 amYYC-MDW
12h 57m2 stops
$282WestJet
Find Deal
Fri, Feb 7
12:30 am - 10:12 amYYC-MDW
8h 42m1 stop
$304WestJet
Find Deal
Thu, Feb 6
4:35 pm - 12:34 pmYYC-MDW
18h 59m1 stop
1:29 pm - 9:04 amMDW-YYC
20h 35m2 stops
Wed, Nov 6 - Thu, Nov 14
4:35 pm - 12:34 pmYYC-MDW
18h 59m1 stop
12:00 pm - 9:45 pmMDW-YYC
10h 45m1 stop
Wed, Nov 6 - Thu, Nov 14
4:35 pm - 12:34 pmYYC-MDW
18h 59m1 stop
12:00 pm - 9:45 pmMDW-YYC
10h 45m1 stop
Wed, Nov 6 - Thu, Nov 14
4:35 pm - 12:34 pmYYC-MDW
18h 59m1 stop
12:00 pm - 9:45 pmMDW-YYC
10h 45m1 stop
Wed, Nov 6 - Thu, Nov 14
9:55 am - 9:59 amYYC-MDW
23h 04m1 stop
9:30 am - 9:46 pmMDW-YYC
13h 16m2 stops
$855WestJet
Find Deal
Tue, Nov 5 - Thu, Nov 14
9:55 am - 9:59 amYYC-MDW
23h 04m1 stop
9:30 am - 9:46 pmMDW-YYC
13h 16m2 stops
$856WestJet
Find Deal
Tue, Nov 5 - Thu, Nov 14
8:00 am - 6:29 pmYYC-MDW
9h 29m2 stops
9:31 am - 8:35 pmMDW-YYC
12h 04m2 stops
$874Delta
Find Deal
Tue, Nov 5 - Thu, Nov 14
7:10 am - 10:20 amYYC-MDW
26h 10m1 stop
11:15 am - 3:28 pmMDW-YYC
29h 13m1 stop
$909Porter Airlines
Find Deal
Tue, Nov 5 - Thu, Nov 14
7:10 am - 10:20 amYYC-MDW
26h 10m1 stop
11:15 am - 3:28 pmMDW-YYC
29h 13m1 stop
$912Porter Airlines
Find Deal
Tue, Nov 5 - Wed, Nov 13
6:45 am - 9:38 pmYYC-MDW
13h 53m2 stops
9:31 am - 8:35 pmMDW-YYC
12h 04m2 stops
$949Delta
Find Deal
Tue, Nov 5 - Wed, Nov 13

Porter Airlines flights from Calgary to Chicago Midway Airport

Our best Porter Airlines deals on Calgary to Chicago Midway Airport flight tickets
Porter Airlines
Nov 28
YYC4:25 pmCalgary
16h 55m
1 stop
MDW10:20 amChicago Midway
Dec 7
MDW12:55 pmChicago Midway
9h 41m
2 stops
YYC9:36 pmCalgary
Porter Airlines
Nov 28
YYC7:10 amCalgary
26h 10m
1 stop
MDW10:20 amChicago Midway
Dec 8
MDW11:15 amChicago Midway
29h 13m
1 stop
YYC3:28 pmCalgary
Porter Airlines
Nov 23
YYC12:55 pmCalgary
20h 25m
1 stop
MDW10:20 amChicago Midway
Nov 24
MDW5:35 pmChicago Midway
22h 53m
1 stop
YYC3:28 pmCalgary

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
Jan 9
YYC6:35 amCalgary
10h 12m
1 stop
MDW5:47 pmChicago Midway
Jan 12
MDW9:34 amChicago Midway
12h 19m
2 stops
YYC8:53 pmCalgary
Delta
Jan 27
YYC6:35 amCalgary
10h 12m
1 stop
MDW5:47 pmChicago Midway
Jan 30
MDW9:34 amChicago Midway
12h 19m
2 stops
YYC8:53 pmCalgary
Delta
Feb 13
YYC7:45 amCalgary
9h 26m
1 stop
MDW6:11 pmChicago Midway
Feb 19
MDW10:10 amChicago Midway
10h 54m
1 stop
YYC8:04 pmCalgary

How to get the cheapest flight ticket from Calgary to Chicago Midway Airport

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

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

No. A direct flight is the cheapest option for a flight between Calgary to Chicago Midway Airport.

When to book flights from Calgary to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Calgary to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Calgary to Chicago Midway Airport (YYC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago Midway Airport

Best Price Found

$136

Fastest flight time

5h 35m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Calgary in the past 72 hours is $136. The best round-trip flight deal from Calgary to Chicago Midway Airport found on momondo in the last 72 hours is $221.
The fastest flight from Calgary to Chicago Midway Airport takes 5h 35m
There are no direct flights from Calgary to Chicago Midway Airport. Popular non-direct route for this connection is Calgary Airport - Chicago Midway Airport.

  • How far is Calgary to Chicago Midway by plane?

    There are 1396.3 mi between Calgary and Chicago Midway. 5h 37m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Calgary Airport to Chicago Midway Airport?

    Prices for flights from Calgary Airport to Chicago Midway Airport are updated daily.

  • How old do you have to be to fly from Calgary Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Calgary Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.


Why use momondo?

Why should I use momondo to find a flight deal from Calgary to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Calgary to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Calgary to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Calgary on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Calgary to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Calgary.

I’m not ready to book a flight from Calgary to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Calgary to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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