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Cheap flights from Calgary to Chicago from $138

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 9/20. 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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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Delta Logo
6:40 am - 1:03 pmYYC-MDW
5h 23m1 stop
Delta Logo
9:20 am - 11:02 pmMDW-YYC
14h 42m2 stops
$244Delta
Find Deal
Wed, Sep 10 - Sat, Sep 13
Logo
10:00 am - 11:17 pmYYC-MDW
12h 17m1 stop
Logo
6:20 am - 8:00 pmMDW-YYC
14h 40m1 stop
$339
Find Deal
Sat, Sep 6 - Mon, Sep 8
Delta Logo
6:40 am - 5:37 pmYYC-MDW
9h 57m1 stop
Delta Logo
1:43 pm - 8:43 pmMDW-YYC
8h 00m1 stop
$349Delta
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Wed, Sep 3 - Tue, Sep 9
Logo
12:30 am - 4:00 pmYYC-MDW
14h 30m1 stop
Logo
6:20 am - 8:00 pmMDW-YYC
14h 40m1 stop
$373
Find Deal
Thu, Sep 18 - Sun, Sep 21
Logo
12:30 am - 3:58 pmYYC-MDW
14h 28m1 stop
Logo
6:20 am - 8:00 pmMDW-YYC
14h 40m1 stop
$374
Find Deal
Tue, Sep 9 - Mon, Sep 15
Logo
7:35 pm - 9:23 amYYC-MDW
12h 48m2 stops
Logo
6:20 am - 8:00 pmMDW-YYC
14h 40m1 stop
$382
Find Deal
Sat, Sep 6 - Mon, Sep 8
Porter Airlines Logo
8:00 am - 8:39 amYYC-MDW
23h 39m2 stops
Porter Airlines Logo
9:35 am - 10:28 pmMDW-YYC
13h 53m2 stops
$428Porter Airlines
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Sun, Sep 14 - Sun, Sep 21
Porter Airlines Logo
8:20 am - 10:05 amYYC-MDW
24h 45m2 stops
Porter Airlines Logo
11:00 am - 8:50 pmMDW-YYC
10h 50m2 stops
$552Porter Airlines
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Thu, Nov 20 - Tue, Nov 25
WestJet Logo
7:00 am - 9:12 pmYYC-MDW
13h 12m2 stops
WestJet Logo
10:31 am - 8:52 pmMDW-YYC
11h 21m2 stops
$608WestJet
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Sat, Sep 6 - Mon, Sep 8
WestJet Logo
12:30 am - 9:36 amYYC-MDW
8h 06m1 stop
WestJet Logo
10:31 am - 8:52 pmMDW-YYC
11h 21m2 stops
$611WestJet
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Fri, Sep 5 - Mon, Sep 8

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
Sep 6
YYC7:00 amCalgary
13h 12m
2 stops
MDW9:12 pmChicago Midway
Sep 8
MDW10:31 amChicago Midway
11h 21m
2 stops
YYC8:52 pmCalgary
$608
Find similar
WestJet
Sep 5
YYC12:30 amCalgary
8h 06m
1 stop
MDW9:36 amChicago Midway
Sep 8
MDW10:31 amChicago Midway
11h 21m
2 stops
YYC8:52 pmCalgary
$611
Find similar
WestJet
Dec 11
YYC6:35 amCalgary
10h 32m
1 stop
MDW6:07 pmChicago Midway
Dec 15
MDW10:35 amChicago Midway
11h 27m
2 stops
YYC9:02 pmCalgary
$623
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Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
Sep 10
YYC6:40 amCalgary
5h 23m
1 stop
MDW1:03 pmChicago Midway
Sep 13
MDW9:20 amChicago Midway
14h 42m
2 stops
YYC11:02 pmCalgary
$244
Find similar
Delta
Sep 3
YYC6:40 amCalgary
9h 57m
1 stop
MDW5:37 pmChicago Midway
Sep 9
MDW1:43 pmChicago Midway
8h 00m
1 stop
YYC8:43 pmCalgary
$349
Find similar
Delta
Sep 4
YYC6:40 amCalgary
5h 23m
1 stop
MDW1:03 pmChicago Midway
Sep 9
MDW1:43 pmChicago Midway
8h 00m
1 stop
YYC8:43 pmCalgary
$393
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 July 31, 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

Wed 9/10

6:40 am-1:03 pm

1 stop5h 23m

Chicago Midway

Sat 9/13

9:20 am-11:02 pm

2 stops14h 42m

$244

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 9/6

10:00 am-11:17 pm

1 stop12h 17m

Chicago Midway

Mon 9/8

6:20 am-8:00 pm

1 stop14h 40m

$339

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 9/3

6:40 am-5:37 pm

1 stop9h 57m

Chicago Midway

Tue 9/9

1:43 pm-8:43 pm

1 stop8h 00m

$349

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 9/18

12:30 am-4:00 pm

1 stop14h 30m

Chicago Midway

Sun 9/21

6:20 am-8:00 pm

1 stop14h 40m

$373

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/9

12:30 am-3:58 pm

1 stop14h 28m

Chicago Midway

Mon 9/15

6:20 am-8:00 pm

1 stop14h 40m

$374

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 9/6

7:35 pm-9:23 am

2 stops12h 48m

Chicago Midway

Mon 9/8

6:20 am-8:00 pm

1 stop14h 40m

$382

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 9/14

8:00 am-8:39 am

2 stops23h 39m

Chicago Midway

Sun 9/21

9:35 am-10:28 pm

2 stops13h 53m

$428

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 11/20

8:20 am-10:05 am

2 stops24h 45m

Chicago Midway

Tue 11/25

11:00 am-8:50 pm

2 stops10h 50m

$552

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 9/6

7:00 am-9:12 pm

2 stops13h 12m

Chicago Midway

Mon 9/8

10:31 am-8:52 pm

2 stops11h 21m

$608

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 9/5

12:30 am-9:36 am

1 stop8h 06m

Chicago Midway

Mon 9/8

10:31 am-8:52 pm

2 stops11h 21m

$611

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

Best Price Found

$138

Fastest flight time

5h 23m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Calgary in the past 72 hours is $138. The best round-trip flight deal from Calgary to Chicago Midway Airport found on momondo in the last 72 hours is $244.
The fastest flight from Calgary to Chicago Midway Airport takes 5h 23m
There are no direct flights from Calgary to Chicago Midway Airport. Popular non-direct route for this connection is Calgary Airport - 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
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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