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Cheap flights from Alberta to Chicago from $196

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Alberta to Chicago departing on 11/21. 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 Alberta to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:45 am - 5:37 pm
YYC
-
MDW
9h 52m
2 stops
Delta Logo
12:30 pm - 9:54 pm
MDW
-
YYC
9h 24m
1 stop
$267Delta
Mon, Nov 23 - Thu, Nov 26
Delta Logo
7:45 am - 3:50 pm
YYC
-
MDW
8h 05m
1 stop
Delta Logo
9:55 am - 12:13 am
MDW
-
YYC
14h 18m
2 stops
$298Delta
Wed, Nov 11 - Mon, Nov 23
Delta Logo
7:45 am - 3:50 pm
YYC
-
MDW
8h 05m
1 stop
Delta Logo
9:55 am - 12:13 am
MDW
-
YYC
14h 18m
2 stops
$311Delta
Wed, Nov 11 - Tue, Nov 24
Delta Logo
7:45 am - 3:50 pm
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 pm - 9:54 pm
MDW
-
YYC
9h 24m
1 stop
$329Delta
Wed, Nov 11 - Tue, Nov 24
Delta Logo
7:00 am - 4:39 pm
YYC
-
MDW
8h 39m
2 stops
Delta Logo
12:28 pm - 8:30 pm
MDW
-
YYC
9h 02m
1 stop
$331Delta
Mon, Oct 26 - Wed, Oct 28
Delta Logo
7:00 am - 4:39 pm
YYC
-
MDW
8h 39m
2 stops
Delta Logo
12:28 pm - 8:30 pm
MDW
-
YYC
9h 02m
1 stop
$332Delta
Mon, Oct 26 - Fri, Oct 30
Delta Logo
12:30 am - 9:52 am
YYC
-
MDW
8h 22m
1 stop
Delta Logo
9:59 am - 8:15 pm
MDW
-
YYC
10h 16m
2 stops
$336Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
12:30 am - 9:52 am
YYC
-
MDW
8h 22m
1 stop
Delta Logo
12:28 pm - 12:12 am
MDW
-
YYC
11h 44m
2 stops
$344Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
7:45 am - 10:25 pm
YYC
-
MDW
13h 40m
2 stops
Delta Logo
12:28 pm - 12:12 am
MDW
-
YYC
11h 44m
2 stops
$346Delta
Fri, Oct 30 - Mon, Nov 2
Multiple Airlines Logo
12:55 am - 2:35 pm
YEG
-
MDW
12h 40m
1 stop
Multiple Airlines Logo
11:45 am - 11:55 pm
MDW
-
YEG
13h 10m
1 stop
$461Multiple Airlines
Mon, Oct 12 - Sat, Oct 17

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Delta flights from Alberta to Chicago Midway Airport

Our best Delta deals on Alberta to Chicago Midway Airport flight tickets
Delta
Nov 23
YYC7:45 amCalgary
9h 52m
2 stops
MDW5:37 pmChicago Midway
Nov 26
MDW12:30 pmChicago Midway
9h 24m
1 stop
YYC9:54 pmCalgary
$267
Delta
Nov 11
YYC7:45 amCalgary
8h 05m
1 stop
MDW3:50 pmChicago Midway
Nov 25
MDW12:30 pmChicago Midway
11h 43m
2 stops
YYC12:13 amCalgary
$298
Delta
Nov 11
YYC7:45 amCalgary
8h 05m
1 stop
MDW3:50 pmChicago Midway
Nov 24
MDW9:55 amChicago Midway
14h 18m
2 stops
YYC12:13 amCalgary
$311

Porter Airlines flights from Alberta to Chicago Midway Airport

Our best Porter Airlines deals on Alberta to Chicago Midway Airport flight tickets
Porter Airlines
Sep 17
YEG11:50 amEdmonton
22h 10m
2 stops
MDW11:00 amChicago Midway
Sep 21
MDW11:45 amChicago Midway
10h 45m
2 stops
YEG9:30 pmEdmonton
$604
Porter Airlines
Sep 17
YEG11:50 amEdmonton
25h 45m
2 stops
MDW2:35 pmChicago Midway
Sep 21
MDW11:45 amChicago Midway
10h 45m
2 stops
YEG9:30 pmEdmonton
$617
Porter Airlines
Sep 2
YEG11:50 amEdmonton
22h 10m
2 stops
MDW11:00 amChicago Midway
Sep 9
MDW11:45 amChicago Midway
10h 45m
2 stops
YEG9:30 pmEdmonton
$619

momondo Fare Finder

 
Customize your flight search to find flights from Alberta 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 19, 2026.
Use the filters below to find and compare flights from Alberta 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

Mon 11/23

7:45 am-5:37 pm

2 stops9h 52m

Chicago Midway

Thu 11/26

12:30 pm-9:54 pm

1 stop9h 24m

$267

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/11

7:45 am-3:50 pm

1 stop8h 05m

Chicago Midway

Mon 11/23

9:55 am-12:13 am

2 stops14h 18m

$298

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/11

7:45 am-3:50 pm

1 stop8h 05m

Chicago Midway

Tue 11/24

9:55 am-12:13 am

2 stops14h 18m

$311
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/11

7:45 am-3:50 pm

1 stop8h 05m

Chicago Midway

Tue 11/24

12:30 pm-9:54 pm

1 stop9h 24m

$329

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 10/26

7:00 am-4:39 pm

2 stops8h 39m

Chicago Midway

Wed 10/28

12:28 pm-8:30 pm

1 stop9h 02m

$331

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 10/26

7:00 am-4:39 pm

2 stops8h 39m

Chicago Midway

Fri 10/30

12:28 pm-8:30 pm

1 stop9h 02m

$332

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/29

12:30 am-9:52 am

1 stop8h 22m

Chicago Midway

Mon 11/2

9:59 am-8:15 pm

2 stops10h 16m

$336

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/29

12:30 am-9:52 am

1 stop8h 22m

Chicago Midway

Mon 11/2

12:28 pm-12:12 am

2 stops11h 44m

$344

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 10/30

7:45 am-10:25 pm

2 stops13h 40m

Chicago Midway

Mon 11/2

12:28 pm-12:12 am

2 stops11h 44m

$346

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Mon 10/12

12:55 am-2:35 pm

1 stop12h 40m

Chicago Midway

Sat 10/17

11:45 am-11:55 pm

1 stop13h 10m

$461

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 Alberta 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 Alberta to Chicago Midway Airport flights?

You could potentially save up to 21% on your flight if you consider stops on a Alberta to Chicago Midway Airport flight.

Cheap Alberta to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Alberta to Chicago Midway Airport

Fastest flight time

5h 24m

Direct flights

None
The fastest flight from Alberta to Chicago Midway Airport takes 5h 24m
There are no direct flights from Alberta to Chicago Midway Airport. There are no popular flight routes from Alberta to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Alberta to Chicago Midway Airport

  • When did momondo last update prices for flights from Alberta to Chicago Midway Airport?

    Prices for flights from Alberta to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Alberta to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Alberta to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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 Alberta to Chicago?

It is quick and easy to find Alberta to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Alberta to Chicago with flexible booking policies on momondo?

Flights from Alberta to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Alberta to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Alberta to Chicago.

I’m not ready to book a flight from Alberta to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Alberta to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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