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.

$139 Cheap Flights from Calgary to Chicago Midway Airport in 2025/26

1 adult

0 bags

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Find the cheapest flights from Calgary to Chicago

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One-way

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Cheap round-trip flights

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6:30 am - 4:16 pm

YYC

MDW

8h 46m1 stop

9:33 am - 8:54 pm

MDW

YYC

12h 21m2 stops

$224Delta

Sat, Jan 31 - Sat, Feb 7

6:30 am - 1:09 pm

YYC

MDW

5h 39m1 stop

1:51 pm - 8:54 pm

MDW

YYC

8h 03m1 stop

$244Delta

Fri, Jan 30 - Fri, Feb 6

7:55 am - 6:25 pm

YYC

MDW

9h 30m1 stop

6:25 am - 7:09 pm

MDW

YYC

13h 44m1 stop

$257Multiple Airlines

Mon, Feb 23 - Thu, Feb 26

12:30 am - 9:55 am

YYC

MDW

8h 25m1 stop

9:32 am - 8:58 pm

MDW

YYC

12h 26m2 stops

$263Delta

Tue, Mar 31 - Sun, Apr 5

12:30 am - 12:30 pm

YYC

MDW

11h 00m2 stops

9:20 am - 7:12 pm

MDW

YYC

10h 52m2 stops

$270Delta

Tue, Apr 14 - Wed, Apr 22

9:15 am - 6:31 pm

YYC

MDW

8h 16m1 stop

6:00 am - 11:06 pm

MDW

YYC

18h 06m2 stops

$274Delta

Tue, May 26 - Sat, May 30

6:30 am - 5:55 pm

YYC

MDW

10h 25m2 stops

9:50 am - 11:05 pm

MDW

YYC

14h 15m2 stops

$282Delta

Tue, Feb 10 - Tue, Feb 17

6:30 am - 1:09 pm

YYC

MDW

5h 39m1 stop

9:50 am - 8:54 pm

MDW

YYC

12h 04m1 stop

$293Delta

Wed, Jan 14 - Sun, Jan 18

1:00 am - 6:31 pm

YYC

MDW

16h 31m2 stops

1:00 pm - 6:25 pm

MDW

YYC

6h 25m1 stop

$299Delta

Mon, May 25 - Sat, May 30

12:15 am - 12:46 pm

YYC

MDW

11h 31m2 stops

9:33 am - 8:54 pm

MDW

YYC

12h 21m2 stops

$300Delta

Fri, Jan 30 - Sat, Feb 7

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets

Delta

Jan 31

YYC6:30 amCalgary

8h 46m

1 stop

MDW4:16 pmChicago Midway

Feb 7

MDW11:45 amChicago Midway

10h 09m

1 stop

YYC8:54 pmCalgary

$224

Find similar

Delta

Jan 30

YYC6:30 amCalgary

5h 39m

1 stop

MDW1:09 pmChicago Midway

Feb 6

MDW1:51 pmChicago Midway

8h 03m

1 stop

YYC8:54 pmCalgary

$244

Find similar

Delta

Mar 31

YYC12:30 amCalgary

8h 25m

1 stop

MDW9:55 amChicago Midway

Apr 5

MDW9:32 amChicago Midway

12h 26m

2 stops

YYC8:58 pmCalgary

$263

Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets

WestJet

Feb 22

YYC12:15 amCalgary

11h 31m

2 stops

MDW12:46 pmChicago Midway

Feb 26

MDW9:50 amChicago Midway

12h 08m

2 stops

YYC8:58 pmCalgary

$488

Find similar

WestJet

Jan 14

YYC6:30 pmCalgary

13h 22m

2 stops

MDW8:52 amChicago Midway

Jan 18

MDW9:32 amChicago Midway

12h 30m

2 stops

YYC9:02 pmCalgary

$516

Find similar

WestJet

Apr 1

YYC6:30 pmCalgary

16h 59m

2 stops

MDW12:29 pmChicago Midway

Apr 5

MDW1:09 pmChicago Midway

8h 49m

2 stops

YYC8:58 pmCalgary

$523

Find similar

momondo Fare Finder

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

Sat 1/31

6:30 am-4:16 pm

1 stop8h 46m

Chicago Midway

Sat 2/7

9:33 am-8:54 pm

2 stops12h 21m

$224

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 1/30

6:30 am-1:09 pm

1 stop5h 39m

Chicago Midway

Fri 2/6

1:51 pm-8:54 pm

1 stop8h 03m

$244

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 2/23

7:55 am-6:25 pm

1 stop9h 30m

Chicago Midway

Thu 2/26

6:25 am-7:09 pm

1 stop13h 44m

$257

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 3/31

12:30 am-9:55 am

1 stop8h 25m

Chicago Midway

Sun 4/5

9:32 am-8:58 pm

2 stops12h 26m

$263

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 4/14

12:30 am-12:30 pm

2 stops11h 00m

Chicago Midway

Wed 4/22

9:20 am-7:12 pm

2 stops10h 52m

$270

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/26

9:15 am-6:31 pm

1 stop8h 16m

Chicago Midway

Sat 5/30

6:00 am-11:06 pm

2 stops18h 06m

$274

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 2/10

6:30 am-5:55 pm

2 stops10h 25m

Chicago Midway

Tue 2/17

9:50 am-11:05 pm

2 stops14h 15m

$282

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 1/14

6:30 am-1:09 pm

1 stop5h 39m

Chicago Midway

Sun 1/18

9:50 am-8:54 pm

1 stop12h 04m

$293

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/25

1:00 am-6:31 pm

2 stops16h 31m

Chicago Midway

Sat 5/30

1:00 pm-6:25 pm

1 stop6h 25m

$299

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 1/30

12:15 am-12:46 pm

2 stops11h 31m

Chicago Midway

Sat 2/7

9:33 am-8:54 pm

2 stops12h 21m

$300

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 is the most popular carrier 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

Fastest flight time	5h 32m
Direct flights	None

The fastest flight from Calgary to Chicago Midway Airport takes 5h 32m

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 32m 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.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

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.