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Cheap flights from Alberta to Chicago from $157

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 9/5. 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

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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 - 9:45 pm
YYC
-
MDW
13h 00m
2 stops
Delta Logo
6:00 am - 11:13 pm
MDW
-
YYC
18h 13m
2 stops
$264Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
7:45 am - 9:45 pm
YYC
-
MDW
13h 00m
2 stops
Delta Logo
6:00 am - 11:13 pm
MDW
-
YYC
18h 13m
2 stops
$265Delta
Thu, Oct 29 - Mon, Nov 2
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
$319Delta
Thu, Oct 29 - Mon, Nov 2
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
$320Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
7:45 am - 4:50 pm
YYC
-
MDW
8h 05m
1 stop
Delta Logo
6:00 am - 11:13 pm
MDW
-
YYC
18h 13m
2 stops
$326Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
7:00 am - 4:15 pm
YYC
-
MDW
8h 15m
1 stop
Delta Logo
1:51 pm - 8:35 pm
MDW
-
YYC
7h 44m
1 stop
$349Delta
Wed, Aug 12 - Mon, Aug 17
Delta Logo
7:45 am - 4:50 pm
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 pm - 8:54 pm
MDW
-
YYC
9h 24m
1 stop
$350Delta
Fri, Oct 30 - Mon, Nov 2
Porter Airlines Logo
11:50 am - 9:40 am
YEG
-
MDW
20h 50m
2 stops
Porter Airlines Logo
10:25 am - 11:24 am
MDW
-
YEG
25h 59m
1 stop
$504Porter Airlines
Sat, Jul 4 - Sat, Jul 11
Porter Airlines Logo
11:50 pm - 2:35 pm
YEG
-
MDW
13h 45m
1 stop
Porter Airlines Logo
10:25 am - 11:24 am
MDW
-
YEG
25h 59m
1 stop
$542Porter Airlines
Sun, Jun 28 - Sun, Jul 5
Multiple Airlines Logo
12:55 am - 2:35 pm
YEG
-
MDW
12h 40m
1 stop
Multiple Airlines Logo
10:25 am - 9:35 pm
MDW
-
YEG
12h 10m
2 stops
$551Multiple Airlines
Mon, Jul 13 - Sun, Jul 19

Delta flights from Alberta to Chicago Midway Airport

Our best Delta deals on Alberta to Chicago Midway Airport flight tickets
Delta
Oct 29
YYC7:45 amCalgary
13h 00m
2 stops
MDW9:45 pmChicago Midway
Nov 2
MDW6:00 amChicago Midway
18h 13m
2 stops
YYC11:13 pmCalgary
$264
Delta
Oct 29
YYC7:45 amCalgary
13h 00m
2 stops
MDW9:45 pmChicago Midway
Nov 2
MDW6:00 amChicago Midway
18h 13m
2 stops
YYC11:13 pmCalgary
$265
Delta
Oct 29
YYC7:45 amCalgary
8h 05m
1 stop
MDW4:50 pmChicago Midway
Nov 2
MDW12:30 pmChicago Midway
11h 43m
2 stops
YYC11:13 pmCalgary
$319

Porter Airlines flights from Alberta to Chicago Midway Airport

Our best Porter Airlines deals on Alberta to Chicago Midway Airport flight tickets
Porter Airlines
Jul 4
YEG11:50 amEdmonton
20h 50m
2 stops
MDW9:40 amChicago Midway
Jul 11
MDW10:25 amChicago Midway
25h 59m
1 stop
YEG11:24 amEdmonton
$504
Porter Airlines
Jun 28
YEG11:50 pmEdmonton
13h 45m
1 stop
MDW2:35 pmChicago Midway
Jul 5
MDW10:25 amChicago Midway
25h 59m
1 stop
YEG11:24 amEdmonton
$542
Porter Airlines
Jul 4
YEG11:50 amEdmonton
20h 50m
2 stops
MDW9:40 amChicago Midway
Jul 11
MDW10:25 amChicago Midway
25h 59m
1 stop
YEG11:24 amEdmonton
$567

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 June 3, 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

Thu 10/29

7:45 am-9:45 pm

2 stops13h 00m

Chicago Midway

Mon 11/2

6:00 am-11:13 pm

2 stops18h 13m

$264

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/29

7:45 am-9:45 pm

2 stops13h 00m

Chicago Midway

Mon 11/2

6:00 am-11:13 pm

2 stops18h 13m

$265

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/29

7:45 am-4:50 pm

1 stop8h 05m

Chicago Midway

Mon 11/2

12:30 pm-11:13 pm

2 stops11h 43m

$319

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/29

7:45 am-9:45 pm

2 stops13h 00m

Chicago Midway

Mon 11/2

12:30 pm-8:54 pm

1 stop9h 24m

$320

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/29

7:45 am-4:50 pm

1 stop8h 05m

Chicago Midway

Mon 11/2

6:00 am-11:13 pm

2 stops18h 13m

$326
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 8/12

7:00 am-4:15 pm

1 stop8h 15m

Chicago Midway

Mon 8/17

1:51 pm-8:35 pm

1 stop7h 44m

$349

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 10/30

7:45 am-4:50 pm

1 stop8h 05m

Chicago Midway

Mon 11/2

12:30 pm-8:54 pm

1 stop9h 24m

$350

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sat 7/4

11:50 am-9:40 am

2 stops20h 50m

Chicago Midway

Sat 7/11

10:25 am-11:24 am

1 stop25h 59m

$504

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sun 6/28

11:50 pm-2:35 pm

1 stop13h 45m

Chicago Midway

Sun 7/5

10:25 am-11:24 am

1 stop25h 59m

$542

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Mon 7/13

12:55 am-2:35 pm

1 stop12h 40m

Chicago Midway

Sun 7/19

10:25 am-9:35 pm

2 stops12h 10m

$551

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 61% 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

6h 10m

Direct flights

None
The fastest flight from Alberta to Chicago Midway Airport takes 6h 10m
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
Saint Joseph
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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.

An easier way to manage your Chicago Midway Airport trip

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