Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Calgary to Chicago from $193

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 12/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:45 am - 4:39 pm
YYC
-
MDW
7h 54m
1 stop
Delta Logo
12:28 pm - 11:04 pm
MDW
-
YYC
11h 36m
2 stops
$326Delta
Fri, Oct 30 - Mon, Nov 2
Delta Logo
7:45 am - 4:22 pm
YYC
-
MDW
7h 37m
2 stops
Delta Logo
11:20 am - 8:54 pm
MDW
-
YYC
10h 34m
1 stop
$328Delta
Fri, Dec 25 - Thu, Dec 31
Delta Logo
7:45 am - 4:39 pm
YYC
-
MDW
7h 54m
1 stop
Delta Logo
12:28 pm - 8:30 pm
MDW
-
YYC
9h 02m
1 stop
$333Delta
Fri, Oct 30 - Mon, Nov 2
Delta Logo
7:45 am - 4:39 pm
YYC
-
MDW
7h 54m
1 stop
Delta Logo
12:28 pm - 8:30 pm
MDW
-
YYC
9h 02m
1 stop
$345Delta
Fri, Oct 30 - Mon, Nov 2
Delta Logo
7:00 am - 6:19 pm
YYC
-
MDW
10h 19m
2 stops
Delta Logo
1:19 pm - 8:15 pm
MDW
-
YYC
7h 56m
1 stop
$347Delta
Fri, Oct 2 - Sun, Oct 4
Delta Logo
6:35 am - 1:20 pm
YYC
-
MDW
5h 45m
1 stop
Delta Logo
9:59 am - 7:40 pm
MDW
-
YYC
10h 41m
2 stops
$348Delta
Wed, Sep 9 - Fri, Sep 11
Delta Logo
6:45 am - 1:10 pm
YYC
-
MDW
5h 25m
1 stop
Delta Logo
9:59 am - 7:40 pm
MDW
-
YYC
10h 41m
2 stops
$353Delta
Wed, Sep 2 - Wed, Sep 9
Delta Logo
7:45 am - 4:22 pm
YYC
-
MDW
7h 37m
2 stops
Delta Logo
9:30 am - 8:54 pm
MDW
-
YYC
12h 24m
2 stops
$358Delta
Fri, Dec 25 - Thu, Dec 31
Delta Logo
6:45 am - 10:36 pm
YYC
-
MDW
14h 51m
2 stops
Delta Logo
1:51 pm - 8:35 pm
MDW
-
YYC
7h 44m
1 stop
$368Delta
Tue, Aug 25 - Mon, Aug 31
Delta Logo
7:45 am - 4:22 pm
YYC
-
MDW
7h 37m
2 stops
Delta Logo
11:20 am - 8:54 pm
MDW
-
YYC
10h 34m
1 stop
$373Delta
Thu, Dec 24 - Thu, Dec 31

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
Oct 30
YYC7:45 amCalgary
7h 54m
1 stop
MDW4:39 pmChicago Midway
Nov 2
MDW12:28 pmChicago Midway
11h 36m
2 stops
YYC11:04 pmCalgary
$326
Delta
Dec 25
YYC7:45 amCalgary
7h 37m
2 stops
MDW4:22 pmChicago Midway
Dec 31
MDW11:20 amChicago Midway
10h 34m
1 stop
YYC8:54 pmCalgary
$328
Delta
Oct 30
YYC7:45 amCalgary
7h 54m
1 stop
MDW4:39 pmChicago Midway
Nov 2
MDW12:28 pmChicago Midway
9h 02m
1 stop
YYC8:30 pmCalgary
$333

Porter Airlines flights from Calgary to Chicago Midway Airport

Our best Porter Airlines deals on Calgary to Chicago Midway Airport flight tickets
Porter Airlines
Jul 16
YYC12:00 pmCalgary
20h 40m
2 stops
MDW9:40 amChicago Midway
Jul 20
MDW10:25 amChicago Midway
13h 08m
2 stops
YYC10:33 pmCalgary
$632
Porter Airlines
Jul 17
YYC12:00 pmCalgary
20h 40m
2 stops
MDW9:40 amChicago Midway
Jul 20
MDW10:25 amChicago Midway
13h 08m
2 stops
YYC10:33 pmCalgary
$700
Porter Airlines
Jul 19
YYC12:00 pmCalgary
20h 40m
2 stops
MDW9:40 amChicago Midway
Jul 22
MDW10:25 amChicago Midway
13h 08m
2 stops
YYC10:33 pmCalgary
$726

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 6, 2026.
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

Fri 10/30

7:45 am-4:39 pm

1 stop7h 54m

Chicago Midway

Mon 11/2

12:28 pm-11:04 pm

2 stops11h 36m

$326

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 12/25

7:45 am-4:22 pm

2 stops7h 37m

Chicago Midway

Thu 12/31

11:20 am-8:54 pm

1 stop10h 34m

$328

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 10/30

7:45 am-4:39 pm

1 stop7h 54m

Chicago Midway

Mon 11/2

12:28 pm-8:30 pm

1 stop9h 02m

$333

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 10/30

7:45 am-4:39 pm

1 stop7h 54m

Chicago Midway

Mon 11/2

12:28 pm-8:30 pm

1 stop9h 02m

$345

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 10/2

7:00 am-6:19 pm

2 stops10h 19m

Chicago Midway

Sun 10/4

1:19 pm-8:15 pm

1 stop7h 56m

$347

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 9/9

6:35 am-1:20 pm

1 stop5h 45m

Chicago Midway

Fri 9/11

9:59 am-7:40 pm

2 stops10h 41m

$348
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 9/2

6:45 am-1:10 pm

1 stop5h 25m

Chicago Midway

Wed 9/9

9:59 am-7:40 pm

2 stops10h 41m

$353

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 12/25

7:45 am-4:22 pm

2 stops7h 37m

Chicago Midway

Thu 12/31

9:30 am-8:54 pm

2 stops12h 24m

$358

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 8/25

6:45 am-10:36 pm

2 stops14h 51m

Chicago Midway

Mon 8/31

1:51 pm-8:35 pm

1 stop7h 44m

$368

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 12/24

7:45 am-4:22 pm

2 stops7h 37m

Chicago Midway

Thu 12/31

11:20 am-8:54 pm

1 stop10h 34m

$373

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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

Can stopping save me money on Calgary to Chicago Midway Airport flights?

You could potentially save up to 33% on your flight if you consider stops on a Calgary to Chicago Midway Airport flight.

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 24m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 24m
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

Frequently asked questions about flying from Calgary to Chicago Midway Airport

  • How far is Calgary to Chicago Midway by plane?

    There are 1396.3 mi between Calgary and Chicago Midway. 5h 24m 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 8/5
Wed 8/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago