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Cheap flights from Calgary to Chicago from $167

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 6/6. 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
0 bags

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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 - 9:45 pm
YYC
-
MDW
13h 00m
2 stops
Delta Logo
12:30 pm - 8:54 pm
MDW
-
YYC
9h 24m
1 stop
$252Delta
Tue, Oct 27 - Sat, Oct 31
Delta Logo
6:45 am - 1:07 pm
YYC
-
MDW
5h 22m
1 stop
Delta Logo
1:47 pm - 8:32 pm
MDW
-
YYC
7h 45m
1 stop
$271Delta
Tue, Sep 15 - Wed, Sep 23
Delta Logo
7:45 am - 9:45 pm
YYC
-
MDW
13h 00m
2 stops
Delta Logo
1:00 pm - 8:54 pm
MDW
-
YYC
8h 54m
2 stops
$276Delta
Tue, Oct 27 - Sat, Oct 31
Delta Logo
6:45 am - 6:33 pm
YYC
-
MDW
10h 48m
2 stops
Delta Logo
9:59 am - 11:09 pm
MDW
-
YYC
14h 10m
2 stops
$277Delta
Thu, Aug 20 - Sat, Aug 22
Delta Logo
7:45 am - 4:50 pm
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 pm - 11:13 pm
MDW
-
YYC
11h 43m
2 stops
$322Delta
Sat, Oct 10 - Tue, Oct 13
Delta Logo
6:45 am - 6:33 pm
YYC
-
MDW
10h 48m
2 stops
Delta Logo
1:52 pm - 8:35 pm
MDW
-
YYC
7h 43m
1 stop
$326Delta
Thu, Aug 20 - Wed, Aug 26
Multiple Airlines Logo
9:00 pm - 11:12 am
YYC
-
MDW
13h 12m
2 stops
Multiple Airlines Logo
6:00 am - 5:10 pm
MDW
-
YYC
12h 10m
1 stop
$329Multiple Airlines
Mon, Aug 17 - Wed, Aug 26
Delta Logo
6:35 am - 1:11 pm
YYC
-
MDW
5h 36m
1 stop
Delta Logo
1:47 pm - 8:32 pm
MDW
-
YYC
7h 45m
1 stop
$347Delta
Fri, Sep 11 - Mon, Sep 14
Delta Logo
6:45 am - 6:33 pm
YYC
-
MDW
10h 48m
2 stops
Delta Logo
9:24 am - 8:35 pm
MDW
-
YYC
12h 11m
2 stops
$348Delta
Thu, Aug 20 - Tue, Aug 25
Multiple Airlines Logo
12:30 am - 11:09 am
YYC
-
MDW
9h 39m
1 stop
Multiple Airlines Logo
6:00 am - 5:10 pm
MDW
-
YYC
12h 10m
1 stop
$367Multiple Airlines
Tue, Aug 18 - Wed, Aug 26

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
Aug 13
YYC6:50 amCalgary
5h 23m
1 stop
MDW1:13 pmChicago Midway
Aug 18
MDW1:57 pmChicago Midway
7h 43m
1 stop
YYC8:40 pmCalgary
$514
WestJet
Jun 6
YYC10:15 amCalgary
6h 41m
1 stop
MDW5:56 pmChicago Midway
Jun 8
MDW1:26 pmChicago Midway
7h 39m
1 stop
YYC8:05 pmCalgary
$788
WestJet
Jun 8
YYC8:10 amCalgary
9h 08m
2 stops
MDW6:18 pmChicago Midway
Jun 13
MDW6:35 pmChicago Midway
26h 30m
1 stop
YYC8:05 pmCalgary
$800

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
Oct 27
YYC7:45 amCalgary
13h 00m
2 stops
MDW9:45 pmChicago Midway
Oct 31
MDW12:30 pmChicago Midway
9h 24m
1 stop
YYC8:54 pmCalgary
$252
Delta
Sep 15
YYC6:45 amCalgary
5h 22m
1 stop
MDW1:07 pmChicago Midway
Sep 23
MDW1:47 pmChicago Midway
7h 45m
1 stop
YYC8:32 pmCalgary
$271
Delta
Oct 27
YYC7:45 amCalgary
13h 00m
2 stops
MDW9:45 pmChicago Midway
Oct 31
MDW10:35 amChicago Midway
11h 19m
2 stops
YYC8:54 pmCalgary
$276

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 May 25, 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

Tue 10/27

7:45 am-9:45 pm

2 stops13h 00m

Chicago Midway

Sat 10/31

12:30 pm-8:54 pm

1 stop9h 24m

$252
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/15

6:45 am-1:07 pm

1 stop5h 22m

Chicago Midway

Wed 9/23

1:47 pm-8:32 pm

1 stop7h 45m

$271

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 10/27

7:45 am-9:45 pm

2 stops13h 00m

Chicago Midway

Sat 10/31

1:00 pm-8:54 pm

2 stops8h 54m

$276

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 8/20

6:45 am-6:33 pm

2 stops10h 48m

Chicago Midway

Sat 8/22

9:59 am-11:09 pm

2 stops14h 10m

$277

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 10/10

7:45 am-4:50 pm

1 stop8h 05m

Chicago Midway

Tue 10/13

12:30 pm-11:13 pm

2 stops11h 43m

$322

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 8/20

6:45 am-6:33 pm

2 stops10h 48m

Chicago Midway

Wed 8/26

1:52 pm-8:35 pm

1 stop7h 43m

$326

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 8/17

9:00 pm-11:12 am

2 stops13h 12m

Chicago Midway

Wed 8/26

6:00 am-5:10 pm

1 stop12h 10m

$329

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 9/11

6:35 am-1:11 pm

1 stop5h 36m

Chicago Midway

Mon 9/14

1:47 pm-8:32 pm

1 stop7h 45m

$347

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 8/20

6:45 am-6:33 pm

2 stops10h 48m

Chicago Midway

Tue 8/25

9:24 am-8:35 pm

2 stops12h 11m

$348

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 8/18

12:30 am-11:09 am

1 stop9h 39m

Chicago Midway

Wed 8/26

6:00 am-5:10 pm

1 stop12h 10m

$367

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

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

You could potentially save up to 61% 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 22m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 22m
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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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 22m 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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.
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