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Cheap flights from Calgary to Chicago from $135

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 10/12. 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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Cheap round-trip flights

Delta Logo
6:45 am - 1:08 pmYYC-MDW
5h 23m1 stop
Delta Logo
9:20 am - 1:54 pmMDW-YYC
5h 34m1 stop
$224Delta
Find Deal
dom., oct. 26 - sáb., nov. 1
Multiple Airlines Logo
8:15 pm - 11:38 amYYC-MDW
14h 23m2 stops
Multiple Airlines Logo
6:30 am - 5:06 pmMDW-YYC
11h 36m1 stop
$240Multiple Airlines
Find Deal
lun., nov. 10 - jue., nov. 13
Multiple Airlines Logo
12:20 pm - 12:37 pmYYC-MDW
23h 17m1 stop
Multiple Airlines Logo
6:30 am - 5:06 pmMDW-YYC
11h 36m1 stop
$241Multiple Airlines
Find Deal
jue., oct. 30 - jue., nov. 6
Delta Logo
6:45 am - 5:43 pmYYC-MDW
9h 58m1 stop
Delta Logo
3:00 pm - 8:47 pmMDW-YYC
6h 47m1 stop
$243Delta
Find Deal
sáb., oct. 11 - sáb., oct. 18
Delta Logo
6:40 am - 5:35 pmYYC-MDW
9h 55m1 stop
Delta Logo
1:43 pm - 8:42 pmMDW-YYC
7h 59m1 stop
$255Delta
Find Deal
vie., sep. 26 - lun., sep. 29
Multiple Airlines Logo
12:30 am - 11:38 amYYC-MDW
10h 08m1 stop
Multiple Airlines Logo
6:15 am - 7:09 pmMDW-YYC
13h 54m1 stop
$256Multiple Airlines
Find Deal
lun., nov. 10 - vie., nov. 14
Multiple Airlines Logo
12:30 am - 11:38 amYYC-MDW
10h 08m1 stop
Multiple Airlines Logo
6:15 am - 5:30 pmMDW-YYC
12h 15m2 stops
$257Multiple Airlines
Find Deal
lun., nov. 10 - vie., nov. 14
WestJet Logo
7:00 am - 6:18 pmYYC-MDW
10h 18m2 stops
WestJet Logo
10:49 am - 9:02 pmMDW-YYC
11h 13m2 stops
$564WestJet
Find Deal
jue., dic. 11 - lun., dic. 15
WestJet Logo
7:00 am - 6:18 pmYYC-MDW
10h 18m2 stops
WestJet Logo
10:47 am - 9:02 pmMDW-YYC
11h 15m2 stops
$565WestJet
Find Deal
lun., nov. 10 - jue., nov. 13
WestJet Logo
7:00 am - 10:14 pmYYC-MDW
14h 14m2 stops
WestJet Logo
10:35 am - 10:22 pmMDW-YYC
12h 47m2 stops
$568WestJet
Find Deal
sáb., oct. 11 - sáb., oct. 18

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
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
$564
Find similar
WestJet
Nov 10
YYC7:00 amCalgary
10h 18m
2 stops
MDW6:18 pmChicago Midway
Nov 13
MDW10:47 amChicago Midway
11h 15m
2 stops
YYC9:02 pmCalgary
$565
Find similar
WestJet
Oct 11
YYC7:00 amCalgary
14h 14m
2 stops
MDW10:14 pmChicago Midway
Oct 18
MDW10:35 amChicago Midway
12h 47m
2 stops
YYC10:22 pmCalgary
$568
Find similar

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
Oct 26
YYC6:45 amCalgary
5h 23m
1 stop
MDW1:08 pmChicago Midway
Nov 1
MDW9:20 amChicago Midway
5h 34m
1 stop
YYC1:54 pmCalgary
$224
Find similar
Delta
Oct 11
YYC6:45 amCalgary
9h 58m
1 stop
MDW5:43 pmChicago Midway
Oct 18
MDW3:00 pmChicago Midway
6h 47m
1 stop
YYC8:47 pmCalgary
$243
Find similar
Delta
Sep 26
YYC6:40 amCalgary
9h 55m
1 stop
MDW5:35 pmChicago Midway
Sep 29
MDW1:43 pmChicago Midway
7h 59m
1 stop
YYC8:42 pmCalgary
$255
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 septiembre 16, 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

dom. 10/26

6:45 am-1:08 pm

1 stop5h 23m

Chicago Midway

sáb. 11/1

9:20 am-1:54 pm

1 stop5h 34m

$224

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

lun. 11/10

8:15 pm-11:38 am

2 stops14h 23m

Chicago Midway

jue. 11/13

6:30 am-5:06 pm

1 stop11h 36m

$240

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

jue. 10/30

12:20 pm-12:37 pm

1 stop23h 17m

Chicago Midway

jue. 11/6

6:30 am-5:06 pm

1 stop11h 36m

$241

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

sáb. 10/11

6:45 am-5:43 pm

1 stop9h 58m

Chicago Midway

sáb. 10/18

3:00 pm-8:47 pm

1 stop6h 47m

$243

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

vie. 9/26

6:40 am-5:35 pm

1 stop9h 55m

Chicago Midway

lun. 9/29

1:43 pm-8:42 pm

1 stop7h 59m

$255

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

lun. 11/10

12:30 am-11:38 am

1 stop10h 08m

Chicago Midway

vie. 11/14

6:15 am-7:09 pm

1 stop13h 54m

$256

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

lun. 11/10

12:30 am-11:38 am

1 stop10h 08m

Chicago Midway

vie. 11/14

6:15 am-5:30 pm

2 stops12h 15m

$257

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

jue. 12/11

7:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

lun. 12/15

10:49 am-9:02 pm

2 stops11h 13m

$564

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

lun. 11/10

7:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

jue. 11/13

10:47 am-9:02 pm

2 stops11h 15m

$565

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

sáb. 10/11

7:00 am-10:14 pm

2 stops14h 14m

Chicago Midway

sáb. 10/18

10:35 am-10:22 pm

2 stops12h 47m

$568

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.
Search flight deals

  • How far is Calgary to Chicago Midway by plane?

    There are 1396.3 mi between Calgary and Chicago Midway. 5h 23m 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
Lansing
Portage
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.

An easier way to manage your Chicago Midway Airport trip

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