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Cheap flights from Alberta to Chicago from C$ 194

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 14/4. 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
6:40 a.m. - 5:58 p.m.
YYC
-
MDW
10h 18m
2 stops
Delta Logo
6:23 a.m. - 10:57 p.m.
MDW
-
YYC
17h 34m
2 stops
C$ 314Delta
Mon, 4 May - Thu, 7 May
Delta Logo
7:00 a.m. - 6:36 p.m.
YYC
-
MDW
10h 36m
2 stops
Delta Logo
9:23 a.m. - 7:40 p.m.
MDW
-
YYC
11h 17m
2 stops
C$ 362Delta
Mon, 4 May - Thu, 7 May
Delta Logo
11:00 a.m. - 5:58 p.m.
YYC
-
MDW
5h 58m
1 stop
Delta Logo
9:22 a.m. - 10:20 p.m.
MDW
-
YYC
13h 58m
2 stops
C$ 374Delta
Mon, 4 May - Thu, 7 May
Delta Logo
6:30 a.m. - 1:24 p.m.
YYC
-
MDW
5h 54m
1 stop
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 382Delta
Sat, 11 Apr - Sat, 18 Apr
Delta Logo
12:15 a.m. - 12:29 p.m.
YYC
-
MDW
11h 14m
2 stops
Delta Logo
9:27 a.m. - 7:28 p.m.
MDW
-
YYC
11h 01m
2 stops
C$ 385Delta
Sat, 11 Apr - Sun, 19 Apr
Multiple Airlines Logo
5:50 p.m. - 10:15 a.m.
YEG
-
MDW
15h 25m
1 stop
Multiple Airlines Logo
11:00 a.m. - 9:55 p.m.
MDW
-
YEG
11h 55m
2 stops
C$ 530Multiple Airlines
Mon, 13 Apr - Thu, 16 Apr
Multiple Airlines Logo
5:50 p.m. - 12:10 p.m.
YEG
-
MDW
17h 20m
1 stop
Multiple Airlines Logo
4:05 p.m. - 10:28 a.m.
MDW
-
YEG
19h 23m
1 stop
C$ 544Multiple Airlines
Fri, 3 Apr - Mon, 6 Apr
Porter Airlines Logo
11:55 p.m. - 12:10 p.m.
YEG
-
MDW
11h 15m
1 stop
Porter Airlines Logo
4:05 p.m. - 5:30 p.m.
MDW
-
YEG
26h 25m
2 stops
C$ 606Porter Airlines
Fri, 3 Apr - Mon, 6 Apr
WestJet Logo
7:10 a.m. - 5:56 p.m.
YQU
-
MDW
9h 46m
2 stops
WestJet Logo
9:20 a.m. - 7:30 p.m.
MDW
-
YQU
11h 10m
2 stops
C$ 1,079WestJet
Wed, 20 May - Tue, 9 Jun
WestJet Logo
6:55 a.m. - 6:40 p.m.
YQU
-
MDW
10h 45m
2 stops
WestJet Logo
10:45 a.m. - 11:20 a.m.
MDW
-
YQU
25h 35m
2 stops
C$ 1,251WestJet
Fri, 3 Apr - Fri, 10 Apr

WestJet flights from Alberta to Chicago Midway Airport

Our best WestJet deals on Alberta to Chicago Midway Airport flight tickets
WestJet
9 Apr
YEG12:05 a.m.Edmonton
16h 17m
2 stops
MDW5:22 p.m.Chicago Midway
13 Apr
MDW10:41 a.m.Chicago Midway
11h 14m
2 stops
YEG8:55 p.m.Edmonton
C$ 713
WestJet
13 Apr
YEG6:30 a.m.Edmonton
10h 28m
2 stops
MDW5:58 p.m.Chicago Midway
16 Apr
MDW9:29 a.m.Chicago Midway
16h 11m
2 stops
YEG12:40 a.m.Edmonton
C$ 714
WestJet
9 Apr
YEG12:05 a.m.Edmonton
32h 51m
2 stops
MDW9:56 a.m.Chicago Midway
13 Apr
MDW10:41 a.m.Chicago Midway
11h 14m
2 stops
YEG8:55 p.m.Edmonton
C$ 716

Delta flights from Alberta to Chicago Midway Airport

Our best Delta deals on Alberta to Chicago Midway Airport flight tickets
Delta
4 May
YYC6:40 a.m.Calgary
10h 18m
2 stops
MDW5:58 p.m.Chicago Midway
7 May
MDW6:23 a.m.Chicago Midway
17h 34m
2 stops
YYC10:57 p.m.Calgary
C$ 314
Delta
4 May
YYC6:40 a.m.Calgary
10h 18m
2 stops
MDW5:58 p.m.Chicago Midway
7 May
MDW6:23 a.m.Chicago Midway
17h 34m
2 stops
YYC10:57 p.m.Calgary
C$ 315
Delta
4 May
YYC7:00 a.m.Calgary
10h 36m
2 stops
MDW6:36 p.m.Chicago Midway
7 May
MDW9:23 a.m.Chicago Midway
11h 17m
2 stops
YYC7:40 p.m.Calgary
C$ 362

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 28 February 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

Mon 4/5

6:40 a.m.-5:58 p.m.

2 stops10h 18m

Chicago Midway

Thu 7/5

6:23 a.m.-10:57 p.m.

2 stops17h 34m

C$ 314

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 4/5

7:00 a.m.-6:36 p.m.

2 stops10h 36m

Chicago Midway

Thu 7/5

9:23 a.m.-7:40 p.m.

2 stops11h 17m

C$ 362

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 4/5

11:00 a.m.-5:58 p.m.

1 stop5h 58m

Chicago Midway

Thu 7/5

9:22 a.m.-10:20 p.m.

2 stops13h 58m

C$ 374

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 11/4

6:30 a.m.-1:24 p.m.

1 stop5h 54m

Chicago Midway

Sat 18/4

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

2 stops12h 13m

C$ 382

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 11/4

12:15 a.m.-12:29 p.m.

2 stops11h 14m

Chicago Midway

Sun 19/4

9:27 a.m.-7:28 p.m.

2 stops11h 01m

C$ 385

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Mon 13/4

5:50 p.m.-10:15 a.m.

1 stop15h 25m

Chicago Midway

Thu 16/4

11:00 a.m.-9:55 p.m.

2 stops11h 55m

C$ 530

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 3/4

5:50 p.m.-12:10 p.m.

1 stop17h 20m

Chicago Midway

Mon 6/4

4:05 p.m.-10:28 a.m.

1 stop19h 23m

C$ 544

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 3/4

11:55 p.m.-12:10 p.m.

1 stop11h 15m

Chicago Midway

Mon 6/4

4:05 p.m.-5:30 p.m.

2 stops26h 25m

C$ 606

Grande PrairieChicago

YQU - MDW

YQUMDW

Grande Prairie

Wed 20/5

7:10 a.m.-5:56 p.m.

2 stops9h 46m

Chicago Midway

Tue 9/6

9:20 a.m.-7:30 p.m.

2 stops11h 10m

C$ 1,079

Grande PrairieChicago

YQU - MDW

YQUMDW

Grande Prairie

Fri 3/4

6:55 a.m.-6:40 p.m.

2 stops10h 45m

Chicago Midway

Fri 10/4

10:45 a.m.-11:20 a.m.

2 stops25h 35m

C$ 1,251

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 34% 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

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