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Cheap flights from Calgary to Chicago from $124

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 departing on 12/12. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:30 am - 1:09 pmYYC-MDW
5h 39m1 stop
Delta Logo
10:35 am - 11:15 pmMDW-YYC
13h 40m2 stops
$222Delta
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Thu, Jan 29 - Sat, Feb 28
Multiple Airlines Logo
8:55 am - 12:41 pmYYC-MDW
26h 46m1 stop
Multiple Airlines Logo
11:00 am - 4:40 pmMDW-YYC
30h 40m1 stop
$308Multiple Airlines
Find Deal
Tue, Nov 18 - Thu, Nov 20
Multiple Airlines Logo
8:55 am - 12:41 pmYYC-MDW
26h 46m1 stop
Multiple Airlines Logo
4:15 pm - 4:40 pmMDW-YYC
25h 25m1 stop
$309Multiple Airlines
Find Deal
Tue, Nov 18 - Fri, Nov 21
Multiple Airlines Logo
12:30 am - 11:38 amYYC-MDW
10h 08m1 stop
Multiple Airlines Logo
11:00 am - 9:02 pmMDW-YYC
11h 02m1 stop
$323Multiple Airlines
Find Deal
Mon, Nov 17 - Thu, Nov 20
Multiple Airlines Logo
12:30 am - 11:38 amYYC-MDW
10h 08m1 stop
Multiple Airlines Logo
11:00 am - 9:02 pmMDW-YYC
11h 02m1 stop
$324Multiple Airlines
Find Deal
Mon, Nov 17 - Fri, Nov 21
Multiple Airlines Logo
8:55 am - 11:25 pmYYC-MDW
13h 30m1 stop
Multiple Airlines Logo
12:25 pm - 7:03 amMDW-YYC
19h 38m2 stops
$329Multiple Airlines
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Sat, Jan 31 - Sun, Mar 1
Delta Logo
6:30 am - 5:55 pmYYC-MDW
10h 25m2 stops
Delta Logo
10:35 am - 11:15 pmMDW-YYC
13h 40m2 stops
$402Delta
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Thu, Jan 29 - Sat, Feb 28
WestJet Logo
5:15 pm - 1:07 pmYYC-MDW
18h 52m2 stops
WestJet Logo
9:41 am - 12:44 amMDW-YYC
16h 03m2 stops
$537WestJet
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Fri, Nov 21 - Mon, Nov 24
WestJet Logo
7:00 am - 6:18 pmYYC-MDW
10h 18m2 stops
WestJet Logo
10:49 am - 9:02 pmMDW-YYC
11h 13m2 stops
$567WestJet
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Thu, Dec 11 - Mon, Dec 15
WestJet Logo
7:00 am - 6:18 pmYYC-MDW
10h 18m2 stops
WestJet Logo
10:49 am - 9:02 pmMDW-YYC
11h 13m2 stops
$585WestJet
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Thu, Dec 11 - Mon, Dec 15

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
Nov 21
YYC5:15 pmCalgary
18h 52m
2 stops
MDW1:07 pmChicago Midway
Nov 24
MDW9:41 amChicago Midway
16h 03m
2 stops
YYC12:44 amCalgary
$537
Find similar
WestJet
Dec 11
YYC7:00 amCalgary
10h 18m
2 stops
MDW6:18 pmChicago Midway
Dec 15
MDW10:49 amChicago Midway
11h 13m
2 stops
YYC9:02 pmCalgary
$567
Find similar
WestJet
Dec 11
YYC7:00 amCalgary
10h 18m
2 stops
MDW6:18 pmChicago Midway
Dec 15
MDW10:49 amChicago Midway
11h 13m
2 stops
YYC9:02 pmCalgary
$585
Find similar

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
Jan 29
YYC6:30 amCalgary
5h 39m
1 stop
MDW1:09 pmChicago Midway
Feb 28
MDW10:35 amChicago Midway
13h 40m
2 stops
YYC11:15 pmCalgary
$222
Find similar
Delta
Nov 1
YYC6:45 amCalgary
5h 23m
1 stop
MDW1:08 pmChicago Midway
Nov 9
MDW9:34 amChicago Midway
12h 19m
2 stops
YYC8:53 pmCalgary
$267
Find similar
Delta
Nov 1
YYC12:30 amCalgary
9h 15m
1 stop
MDW10:45 amChicago Midway
Nov 9
MDW9:34 amChicago Midway
12h 19m
2 stops
YYC8:53 pmCalgary
$300
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Calgary to Chicago Midway Airport 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 October 30, 2025.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 1/29

6:30 am-1:09 pm

1 stop5h 39m

Chicago Midway

Sat 2/28

10:35 am-11:15 pm

2 stops13h 40m

$222

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 11/18

8:55 am-12:41 pm

1 stop26h 46m

Chicago Midway

Thu 11/20

11:00 am-4:40 pm

1 stop30h 40m

$308

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 11/18

8:55 am-12:41 pm

1 stop26h 46m

Chicago Midway

Fri 11/21

4:15 pm-4:40 pm

1 stop25h 25m

$309

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 11/17

12:30 am-11:38 am

1 stop10h 08m

Chicago Midway

Thu 11/20

11:00 am-9:02 pm

1 stop11h 02m

$323

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 11/17

12:30 am-11:38 am

1 stop10h 08m

Chicago Midway

Fri 11/21

11:00 am-9:02 pm

1 stop11h 02m

$324

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 1/31

8:55 am-11:25 pm

1 stop13h 30m

Chicago Midway

Sun 3/1

12:25 pm-7:03 am

2 stops19h 38m

$329

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 1/29

6:30 am-5:55 pm

2 stops10h 25m

Chicago Midway

Sat 2/28

10:35 am-11:15 pm

2 stops13h 40m

$402

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 11/21

5:15 pm-1:07 pm

2 stops18h 52m

Chicago Midway

Mon 11/24

9:41 am-12:44 am

2 stops16h 03m

$537

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 12/11

7:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Mon 12/15

10:49 am-9:02 pm

2 stops11h 13m

$567

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 12/11

7:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Mon 12/15

10:49 am-9:02 pm

2 stops11h 13m

$585

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 Chicago from

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

What is the cheapest airline that flies from Calgary to Chicago Midway?

Delta, Porter Airlines, and WestJet are the most popular carriers operating from Calgary to Chicago Midway

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

Direct flights

None
There are no direct flights from Calgary to Chicago Midway Airport. There are no popular flight routes from Calgary to Chicago Midway Airport.
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  • How far is Calgary to Chicago Midway by plane?

    There are 1396.3 mi between Calgary and Chicago Midway. 5h 35m 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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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