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.

$145 Cheap Flights from Calgary to Chicago Midway Airport in 2026

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0 bags

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Find the cheapest flights from Calgary to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:45 am - 1:19 pm

YYC

MDW

5h 34m

1 stop

1:22 pm - 8:05 pm

MDW

YYC

7h 43m

1 stop

$279Delta

Sat, May 16 - Wed, May 20

11:00 am - 6:14 pm

YYC

MDW

6h 14m

1 stop

9:23 am - 6:10 pm

MDW

YYC

9h 47m

2 stops

$283Delta

Tue, May 19 - Sat, May 23

6:45 am - 1:19 pm

YYC

MDW

5h 34m

1 stop

9:23 am - 8:25 pm

MDW

YYC

12h 02m

2 stops

$284Delta

Sun, May 17 - Sun, May 24

12:20 pm - 9:29 pm

YYC

MDW

8h 09m

1 stop

3:29 pm - 8:17 pm

MDW

YYC

29h 48m

2 stops

$285Multiple Airlines

Fri, Feb 27 - Mon, Mar 2

12:20 pm - 9:29 pm

YYC

MDW

8h 09m

1 stop

3:29 pm - 10:46 pm

MDW

YYC

32h 17m

1 stop

$288Multiple Airlines

Fri, Feb 27 - Mon, Mar 2

6:25 pm - 9:40 am

YYC

MDW

14h 15m

1 stop

5:35 pm - 6:15 pm

MDW

YYC

25h 40m

1 stop

$317Multiple Airlines

Mon, May 4 - Thu, May 7

11:00 am - 6:14 pm

YYC

MDW

6h 14m

1 stop

6:30 am - 5:10 pm

MDW

YYC

11h 40m

1 stop

$331Delta

Tue, May 19 - Sat, May 23

11:00 am - 5:58 pm

YYC

MDW

5h 58m

1 stop

1:23 pm - 8:05 pm

MDW

YYC

7h 42m

1 stop

$332Delta

Mon, Apr 27 - Fri, May 1

6:45 am - 1:19 pm

YYC

MDW

5h 34m

1 stop

1:22 pm - 8:05 pm

MDW

YYC

7h 43m

1 stop

$333Delta

Sat, May 16 - Sat, May 23

6:45 am - 5:56 pm

YYC

MDW

10h 11m

1 stop

1:22 pm - 8:05 pm

MDW

YYC

7h 43m

1 stop

$334Delta

Thu, May 14 - Wed, May 20

Delta flights from Calgary to Chicago Midway Airport

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

Delta

May 16

YYC6:45 amCalgary

5h 34m

1 stop

MDW1:19 pmChicago Midway

May 20

MDW1:22 pmChicago Midway

7h 43m

1 stop

YYC8:05 pmCalgary

$279

Delta

May 19

YYC7:00 amCalgary

9h 56m

2 stops

MDW5:56 pmChicago Midway

May 24

MDW9:23 amChicago Midway

12h 02m

2 stops

YYC8:25 pmCalgary

$283

Delta

May 17

YYC6:45 amCalgary

5h 34m

1 stop

MDW1:19 pmChicago Midway

May 24

MDW9:23 amChicago Midway

12h 02m

2 stops

YYC8:25 pmCalgary

$284

WestJet flights from Calgary to Chicago Midway Airport

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

WestJet

Feb 7

YYC6:30 amCalgary

27h 35m

1 stop

MDW11:05 amChicago Midway

Feb 10

MDW10:48 amChicago Midway

25h 55m

1 stop

YYC11:43 amCalgary

$712

WestJet

Feb 11

YYC7:00 amCalgary

10h 36m

2 stops

MDW6:36 pmChicago Midway

Feb 12

MDW9:50 amChicago Midway

10h 22m

2 stops

YYC7:12 pmCalgary

$719

WestJet

Feb 7

YYC11:30 pmCalgary

33h 23m

2 stops

MDW9:53 amChicago Midway

Feb 10

MDW1:51 pmChicago Midway

8h 03m

1 stop

YYC8:54 pmCalgary

$744

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 5/16

6:45 am-1:19 pm

1 stop5h 34m

Chicago Midway

Wed 5/20

1:22 pm-8:05 pm

1 stop7h 43m

$279

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/19

11:00 am-6:14 pm

1 stop6h 14m

Chicago Midway

Sat 5/23

9:23 am-6:10 pm

2 stops9h 47m

$283

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 5/17

6:45 am-1:19 pm

1 stop5h 34m

Chicago Midway

Sun 5/24

9:23 am-8:25 pm

2 stops12h 02m

$284

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 2/27

12:20 pm-9:29 pm

1 stop8h 09m

Chicago Midway

Mon 3/2

3:29 pm-8:17 pm

2 stops29h 48m

$285

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 2/27

12:20 pm-9:29 pm

1 stop8h 09m

Chicago Midway

Mon 3/2

3:29 pm-10:46 pm

1 stop32h 17m

$288

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/4

6:25 pm-9:40 am

1 stop14h 15m

Chicago Midway

Thu 5/7

5:35 pm-6:15 pm

1 stop25h 40m

$317

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/19

11:00 am-6:14 pm

1 stop6h 14m

Chicago Midway

Sat 5/23

6:30 am-5:10 pm

1 stop11h 40m

$331

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 4/27

11:00 am-5:58 pm

1 stop5h 58m

Chicago Midway

Fri 5/1

1:23 pm-8:05 pm

1 stop7h 42m

$332

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 5/16

6:45 am-1:19 pm

1 stop5h 34m

Chicago Midway

Sat 5/23

1:22 pm-8:05 pm

1 stop7h 43m

$333

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 5/14

6:45 am-5:56 pm

1 stop10h 11m

Chicago Midway

Wed 5/20

1:22 pm-8:05 pm

1 stop7h 43m

$334

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 39m
Direct flights	None

The fastest flight from Calgary to Chicago Midway Airport takes 5h 39m

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 39m 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

Schererville

Valparaiso

Munster

Crown Point

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.