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Cheap flights from Calgary to Chicago from $185

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
6:35 am - 1:20 pmYYC  Calgary-MDW Chicago Midway
5h 45m1 stop Minneapolis St Paul
Delta Logo
2:00 pm - 8:42 pmMDW  Chicago Midway-YYC Calgary
7h 42m1 stop Minneapolis St Paul
$297Delta
Tue, Sep 22 - Tue, Sep 29
Delta Logo
12:25 am - 11:54 amYYC  Calgary-MDW Chicago Midway
10h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:27 pm - 10:40 pmMDW  Chicago Midway-YYC Calgary
10h 13m1 stop Minneapolis St Paul
$340Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
7:45 am - 10:33 pmYYC  Calgary-MDW Chicago Midway
13h 48m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
Delta Logo
12:27 pm - 10:40 pmMDW  Chicago Midway-YYC Calgary
10h 13m1 stop Minneapolis St Paul
$350Delta
Fri, Oct 30 - Mon, Nov 2
Delta Logo
12:25 am - 12:47 pmYYC  Calgary-MDW Chicago Midway
11h 22m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
10:01 am - 1:10 amMDW  Chicago Midway-YYC Calgary
15h 09m2 stops Minneapolis St Paul Salt Lake City
$357Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
11:00 am - 6:00 pmYYC  Calgary-MDW Chicago Midway
6h 00m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:27 pm - 8:05 pmMDW  Chicago Midway-YYC Calgary
7h 38m1 stop Detroit Metropolitan Wayne County
$362Delta
Sat, Oct 10 - Tue, Oct 13
Delta Logo
7:00 am - 5:59 pmYYC  Calgary-MDW Chicago Midway
9h 59m2 stops Edmonton Minneapolis St Paul
Delta Logo
12:27 pm - 7:40 pmMDW  Chicago Midway-YYC Calgary
8h 13m2 stops Minneapolis St Paul Edmonton
$364Delta
Sat, Oct 3 - Fri, Oct 23
Delta Logo
8:45 am - 9:54 pmYYC  Calgary-MDW Chicago Midway
13h 09m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
Delta Logo
12:30 pm - 10:58 pmMDW  Chicago Midway-YYC Calgary
10h 28m1 stop Minneapolis St Paul
$381Delta
Wed, Nov 18 - Sun, Nov 22
Delta Logo
7:25 am - 3:39 pmYYC  Calgary-MDW Chicago Midway
8h 14m2 stops Salt Lake City Minneapolis St Paul
Delta Logo
12:30 pm - 10:58 pmMDW  Chicago Midway-YYC Calgary
10h 28m1 stop Minneapolis St Paul
$389Delta
Sat, Nov 14 - Sat, Nov 21
Multiple Airlines Logo
7:00 am - 5:51 pmYYC  Calgary-MDW Chicago Midway
9h 51m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:25 am - 5:10 pmMDW  Chicago Midway-YYC Calgary
11h 45m1 stop Atlanta Hartsfield-Jackson
$392Multiple Airlines
Fri, Sep 11 - Sat, Sep 12
Delta Logo
11:35 pm - 4:47 pmYYC  Calgary-MDW Chicago Midway
16h 12m2 stops Vancouver Intl Minneapolis St Paul
Delta Logo
1:27 pm - 8:15 pmMDW  Chicago Midway-YYC Calgary
7h 48m1 stop Detroit Metropolitan Wayne County
$393Delta
Mon, Oct 19 - Fri, Oct 23

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Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
Sep 22
YYC6:35 amCalgary
5h 45m
1 stop
MDW1:20 pmChicago Midway
Sep 29
MDW2:00 pmChicago Midway
7h 42m
1 stop
YYC8:42 pmCalgary
$297
Delta
Oct 29
YYC12:25 amCalgary
11h 22m
2 stops
MDW12:47 pmChicago Midway
Nov 2
MDW10:01 amChicago Midway
15h 09m
2 stops
YYC1:10 amCalgary
$340
Delta
Aug 27
YYC6:45 amCalgary
5h 25m
1 stop
MDW1:10 pmChicago Midway
Aug 31
MDW1:51 pmChicago Midway
7h 44m
1 stop
YYC8:35 pmCalgary
$343

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
Sep 5
YYC7:00 amCalgary
7h 44m
1 stop
MDW3:44 pmChicago Midway
Sep 8
MDW9:59 amChicago Midway
9h 11m
2 stops
YYC6:10 pmCalgary
$890
WestJet
Sep 5
YYC12:20 amCalgary
8h 50m
1 stop
MDW10:10 amChicago Midway
Sep 9
MDW9:59 amChicago Midway
10h 41m
2 stops
YYC7:40 pmCalgary
$899
WestJet
Sep 5
YYC7:00 amCalgary
7h 57m
2 stops
MDW3:57 pmChicago Midway
Sep 6
MDW9:59 amChicago Midway
8h 01m
1 stop
YYC5:00 pmCalgary
$903

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
Quickest round-trip

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 9/22

6:35 am-1:20 pm

1 stop5h 45m

Chicago Midway

Tue 9/29

2:00 pm-8:42 pm

1 stop7h 42m

$297

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 10/29

12:25 am-11:54 am

1 stop10h 29m

Chicago Midway

Mon 11/2

12:27 pm-10:40 pm

1 stop10h 13m

$340

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 10/30

7:45 am-10:33 pm

2 stops13h 48m

Chicago Midway

Mon 11/2

12:27 pm-10:40 pm

1 stop10h 13m

$350

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 10/29

12:25 am-12:47 pm

2 stops11h 22m

Chicago Midway

Mon 11/2

10:01 am-1:10 am

2 stops15h 09m

$357

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 10/10

11:00 am-6:00 pm

1 stop6h 00m

Chicago Midway

Tue 10/13

1:27 pm-8:05 pm

1 stop7h 38m

$362

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 10/3

7:00 am-5:59 pm

2 stops9h 59m

Chicago Midway

Fri 10/23

12:27 pm-7:40 pm

2 stops8h 13m

$364

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 11/18

8:45 am-9:54 pm

2 stops13h 09m

Chicago Midway

Sun 11/22

12:30 pm-10:58 pm

1 stop10h 28m

$381

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 11/14

7:25 am-3:39 pm

2 stops8h 14m

Chicago Midway

Sat 11/21

12:30 pm-10:58 pm

1 stop10h 28m

$389

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 9/11

7:00 am-5:51 pm

1 stop9h 51m

Chicago Midway

Sat 9/12

6:25 am-5:10 pm

1 stop11h 45m

$392

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Mon 10/19

11:35 pm-4:47 pm

2 stops16h 12m

Chicago Midway

Fri 10/23

1:27 pm-8:15 pm

1 stop7h 48m

$393

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 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

Best Price Found

$185

Fastest flight time

5h 25m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Calgary in the past 72 hours is $185. The best round-trip flight deal from Calgary to Chicago Midway Airport found on momondo in the last 72 hours is $297.
The fastest flight from Calgary to Chicago Midway Airport takes 5h 25m
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 25m 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
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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.

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