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.

$154 Cheap Flights from Calgary to Chicago Midway Airport in 2026

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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.

6:40 am - 10:28 pm

YYC

MDW

14h 48m

2 stops

9:29 am - 11:00 pm

MDW

YYC

14h 31m

2 stops

$267Delta

Sat, Apr 25 - Tue, Apr 28

7:40 am - 10:28 pm

YYC

MDW

13h 48m

2 stops

9:29 am - 11:00 pm

MDW

YYC

14h 31m

2 stops

$269Delta

Tue, Apr 21 - Tue, Apr 28

6:45 am - 1:19 pm

YYC

MDW

5h 34m

1 stop

9:30 am - 8:44 pm

MDW

YYC

12h 14m

2 stops

$272Delta

Sat, May 30 - Sat, Sep 19

6:40 am - 1:32 pm

YYC

MDW

5h 52m

1 stop

9:27 am - 8:40 pm

MDW

YYC

12h 13m

2 stops

$280Delta

Sat, Apr 25 - Mon, Apr 27

7:40 am - 10:28 pm

YYC

MDW

13h 48m

2 stops

9:27 am - 8:40 pm

MDW

YYC

12h 13m

2 stops

$281Delta

Tue, Apr 21 - Mon, Apr 27

6:45 am - 10:17 pm

YYC

MDW

14h 32m

2 stops

9:17 am - 8:38 pm

MDW

YYC

12h 21m

2 stops

$300Delta

Wed, Jul 1 - Sat, Jul 4

6:45 am - 5:56 pm

YYC

MDW

10h 11m

1 stop

9:22 am - 8:30 pm

MDW

YYC

12h 08m

2 stops

$308Delta

Thu, May 28 - Mon, Jun 1

6:45 am - 5:56 pm

YYC

MDW

10h 11m

1 stop

9:22 am - 8:30 pm

MDW

YYC

12h 08m

2 stops

$319Delta

Thu, May 28 - Mon, Jun 1

6:45 am - 5:56 pm

YYC

MDW

10h 11m

1 stop

9:22 am - 8:30 pm

MDW

YYC

12h 08m

2 stops

$322Delta

Thu, May 28 - Mon, Jun 1

6:40 am - 1:32 pm

YYC

MDW

5h 52m

1 stop

9:22 am - 8:30 pm

MDW

YYC

12h 08m

2 stops

$323Delta

Tue, May 5 - Tue, May 12

Delta flights from Calgary to Chicago Midway Airport

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

Delta

Apr 25

YYC6:40 amCalgary

14h 48m

2 stops

MDW10:28 pmChicago Midway

Apr 28

MDW9:29 amChicago Midway

14h 31m

2 stops

YYC11:00 pmCalgary

$267

Delta

Apr 21

YYC7:40 amCalgary

13h 48m

2 stops

MDW10:28 pmChicago Midway

Apr 28

MDW9:29 amChicago Midway

14h 31m

2 stops

YYC11:00 pmCalgary

$269

Delta

May 30

YYC6:45 amCalgary

5h 34m

1 stop

MDW1:19 pmChicago Midway

Sep 19

MDW9:30 amChicago Midway

12h 14m

2 stops

YYC8:44 pmCalgary

$272

WestJet flights from Calgary to Chicago Midway Airport

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

WestJet

Mar 31

YYC6:30 amCalgary

5h 55m

1 stop

MDW1:25 pmChicago Midway

Apr 9

MDW10:45 amChicago Midway

9h 24m

1 stop

YYC7:09 pmCalgary

$752

WestJet

Apr 3

YYC10:00 amCalgary

21h 53m

2 stops

MDW8:53 amChicago Midway

Apr 18

MDW6:38 pmChicago Midway

20h 50m

2 stops

YYC2:28 pmCalgary

$771

WestJet

Apr 3

YYC6:30 amCalgary

11h 10m

1 stop

MDW6:40 pmChicago Midway

Apr 18

MDW9:46 amChicago Midway

11h 54m

1 stop

YYC8:40 pmCalgary

$798

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

Cheapest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 4/25

6:40 am-10:28 pm

2 stops14h 48m

Chicago Midway

Tue 4/28

9:29 am-11:00 pm

2 stops14h 31m

$267

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 4/21

7:40 am-10:28 pm

2 stops13h 48m

Chicago Midway

Tue 4/28

9:29 am-11:00 pm

2 stops14h 31m

$269

Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 5/30

6:45 am-1:19 pm

1 stop5h 34m

Chicago Midway

Sat 9/19

9:30 am-8:44 pm

2 stops12h 14m

$272

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 4/25

6:40 am-1:32 pm

1 stop5h 52m

Chicago Midway

Mon 4/27

9:27 am-8:40 pm

2 stops12h 13m

$280

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 4/21

7:40 am-10:28 pm

2 stops13h 48m

Chicago Midway

Mon 4/27

9:27 am-8:40 pm

2 stops12h 13m

$281

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 7/1

6:45 am-10:17 pm

2 stops14h 32m

Chicago Midway

Sat 7/4

9:17 am-8:38 pm

2 stops12h 21m

$300

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 5/28

6:45 am-5:56 pm

1 stop10h 11m

Chicago Midway

Mon 6/1

9:22 am-8:30 pm

2 stops12h 08m

$308

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 5/28

6:45 am-5:56 pm

1 stop10h 11m

Chicago Midway

Mon 6/1

9:22 am-8:30 pm

2 stops12h 08m

$319

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 5/28

6:45 am-5:56 pm

1 stop10h 11m

Chicago Midway

Mon 6/1

9:22 am-8:30 pm

2 stops12h 08m

$322

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/5

6:40 am-1:32 pm

1 stop5h 52m

Chicago Midway

Tue 5/12

9:22 am-8:30 pm

2 stops12h 08m

$323

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 34m
Direct flights	None

The fastest flight from Calgary to Chicago Midway Airport takes 5h 34m

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 34m 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

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Schererville

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.