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Cheap flights from Alberta to Chicago from C$ 186

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 2/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
6:30 a.m. - 5:37 p.m.
YYC
-
MDW
10h 07m2 stops
Delta Logo
9:50 a.m. - 11:05 p.m.
MDW
-
YYC
14h 15m2 stops
C$ 317Delta
Tue, 24 Feb - Tue, 3 Mar
Multiple Airlines Logo
8:15 p.m. - 4:16 p.m.
YYC
-
MDW
19h 01m2 stops
Multiple Airlines Logo
7:15 a.m. - 7:09 p.m.
MDW
-
YYC
12h 54m1 stop
C$ 327Multiple Airlines
Wed, 25 Feb - Wed, 4 Mar
Multiple Airlines Logo
7:35 p.m. - 11:41 p.m.
YYC
-
MDW
27h 06m1 stop
Multiple Airlines Logo
7:15 a.m. - 7:09 p.m.
MDW
-
YYC
12h 54m1 stop
C$ 328Multiple Airlines
Wed, 25 Feb - Wed, 4 Mar
Multiple Airlines Logo
8:55 a.m. - 7:07 p.m.
YYC
-
MDW
9h 12m1 stop
Multiple Airlines Logo
7:30 a.m. - 7:09 p.m.
MDW
-
YYC
12h 39m1 stop
C$ 330Multiple Airlines
Tue, 24 Feb - Tue, 3 Mar
Multiple Airlines Logo
8:55 a.m. - 7:07 p.m.
YYC
-
MDW
9h 12m1 stop
Multiple Airlines Logo
7:30 a.m. - 7:09 p.m.
MDW
-
YYC
12h 39m1 stop
C$ 331Multiple Airlines
Tue, 24 Feb - Tue, 3 Mar
Delta Logo
6:30 a.m. - 1:06 p.m.
YYC
-
MDW
5h 36m1 stop
Delta Logo
1:51 p.m. - 8:54 p.m.
MDW
-
YYC
8h 03m1 stop
C$ 345Delta
Mon, 2 Feb - Mon, 9 Feb
Multiple Airlines Logo
8:55 a.m. - 12:05 p.m.
YYC
-
MDW
26h 10m1 stop
Multiple Airlines Logo
5:16 p.m. - 11:43 a.m.
MDW
-
YYC
19h 27m1 stop
C$ 370Multiple Airlines
Tue, 27 Jan - Thu, 26 Feb
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m1 stop
Delta Logo
9:20 a.m. - 11:06 p.m.
MDW
-
YYC
14h 46m2 stops
C$ 376Delta
Wed, 22 Apr - Sat, 9 May
Delta Logo
6:40 a.m. - 1:32 p.m.
YYC
-
MDW
5h 52m1 stop
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m2 stops
C$ 387Delta
Sat, 25 Apr - Tue, 5 May
WestJet Logo
12:05 a.m. - 12:46 p.m.
YEG
-
MDW
11h 41m2 stops
WestJet Logo
9:34 a.m. - 8:55 p.m.
MDW
-
YEG
12h 21m2 stops
C$ 722WestJet
Wed, 18 Feb - Mon, 23 Feb

Delta flights from Alberta to Chicago Midway Airport

Our best Delta deals on Alberta to Chicago Midway Airport flight tickets
Delta
24 Feb
YYC6:30 a.m.Calgary
5h 35m
1 stop
MDW1:05 p.m.Chicago Midway
3 Mar
MDW9:50 a.m.Chicago Midway
14h 15m
2 stops
YYC11:05 p.m.Calgary
C$ 317
Delta
2 Feb
YYC6:30 a.m.Calgary
5h 36m
1 stop
MDW1:06 p.m.Chicago Midway
9 Feb
MDW1:51 p.m.Chicago Midway
8h 03m
1 stop
YYC8:54 p.m.Calgary
C$ 345
Delta
22 Apr
YYC6:40 a.m.Calgary
5h 52m
1 stop
MDW1:32 p.m.Chicago Midway
9 May
MDW9:20 a.m.Chicago Midway
14h 46m
2 stops
YYC11:06 p.m.Calgary
C$ 376

WestJet flights from Alberta to Chicago Midway Airport

Our best WestJet deals on Alberta to Chicago Midway Airport flight tickets
WestJet
25 Feb
YYC12:15 a.m.Calgary
11h 31m
2 stops
MDW12:46 p.m.Chicago Midway
27 Feb
MDW10:49 a.m.Chicago Midway
11h 09m
2 stops
YYC8:58 p.m.Calgary
C$ 691
WestJet
25 Feb
YYC12:15 a.m.Calgary
11h 31m
2 stops
MDW12:46 p.m.Chicago Midway
27 Feb
MDW10:49 a.m.Chicago Midway
11h 09m
2 stops
YYC8:58 p.m.Calgary
C$ 708
WestJet
18 Feb
YEG12:05 a.m.Edmonton
11h 41m
2 stops
MDW12:46 p.m.Chicago Midway
23 Feb
MDW9:34 a.m.Chicago Midway
12h 21m
2 stops
YEG8:55 p.m.Edmonton
C$ 722

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 96,600 searches. Data last updated 11 January 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

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 24/2

6:30 a.m.-5:37 p.m.

2 stops10h 07m

Chicago Midway

Tue 3/3

9:50 a.m.-11:05 p.m.

2 stops14h 15m

C$ 317

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 25/2

8:15 p.m.-4:16 p.m.

2 stops19h 01m

Chicago Midway

Wed 4/3

7:15 a.m.-7:09 p.m.

1 stop12h 54m

C$ 327

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 25/2

7:35 p.m.-11:41 p.m.

1 stop27h 06m

Chicago Midway

Wed 4/3

7:15 a.m.-7:09 p.m.

1 stop12h 54m

C$ 328

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 24/2

8:55 a.m.-7:07 p.m.

1 stop9h 12m

Chicago Midway

Tue 3/3

7:30 a.m.-7:09 p.m.

1 stop12h 39m

C$ 330

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 24/2

8:55 a.m.-7:07 p.m.

1 stop9h 12m

Chicago Midway

Tue 3/3

7:30 a.m.-7:09 p.m.

1 stop12h 39m

C$ 331

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 2/2

6:30 a.m.-1:06 p.m.

1 stop5h 36m

Chicago Midway

Mon 9/2

1:51 p.m.-8:54 p.m.

1 stop8h 03m

C$ 345

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 27/1

8:55 a.m.-12:05 p.m.

1 stop26h 10m

Chicago Midway

Thu 26/2

5:16 p.m.-11:43 a.m.

1 stop19h 27m

C$ 370

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 22/4

6:40 a.m.-1:32 p.m.

1 stop5h 52m

Chicago Midway

Sat 9/5

9:20 a.m.-11:06 p.m.

2 stops14h 46m

C$ 376

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 25/4

6:40 a.m.-1:32 p.m.

1 stop5h 52m

Chicago Midway

Tue 5/5

9:27 a.m.-8:40 p.m.

2 stops12h 13m

C$ 387

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 18/2

12:05 a.m.-12:46 p.m.

2 stops11h 41m

Chicago Midway

Mon 23/2

9:34 a.m.-8:55 p.m.

2 stops12h 21m

C$ 722

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 31% 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 35m

Direct flights

None
The fastest flight from Alberta to Chicago Midway Airport takes 5h 35m
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

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

    Prices for flights from Alberta to Chicago Midway Airport refresh daily.

  • 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 you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

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?

Yes. momondo enables you to select and highlight flights to Chicago from Alberta with this policy.

How can momondo help me find flights from Alberta 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 Alberta.

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

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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