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Cheap flights from Alberta to Chicago from C$ 192

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 1/11. 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
6:35 a.m. - 1:07 p.m.YYC-MDW
5h 32m1 stop
Delta Logo
1:47 p.m. - 8:53 p.m.MDW-YYC
8h 06m1 stop
C$ 311Delta
Find Deal
Tue, 18 Nov - Tue, 25 Nov
Delta Logo
7:45 a.m. - 6:18 p.m.YYC-MDW
9h 33m2 stops
Delta Logo
1:47 p.m. - 8:53 p.m.MDW-YYC
8h 06m1 stop
C$ 342Delta
Find Deal
Tue, 18 Nov - Tue, 25 Nov
Multiple Airlines Logo
8:35 p.m. - 11:38 a.m.YEG-MDW
14h 03m2 stops
Multiple Airlines Logo
6:15 a.m. - 12:11 p.m.MDW-YEG
30h 56m1 stop
C$ 365Multiple Airlines
Find Deal
Mon, 3 Nov - Mon, 10 Nov
Multiple Airlines Logo
12:45 a.m. - 6:39 p.m.YEG-MDW
16h 54m1 stop
Multiple Airlines Logo
1:56 p.m. - 12:11 p.m.MDW-YEG
23h 15m1 stop
C$ 368Multiple Airlines
Find Deal
Fri, 14 Nov - Wed, 19 Nov
Multiple Airlines Logo
12:30 a.m. - 11:38 a.m.YYC-MDW
10h 08m1 stop
Multiple Airlines Logo
1:56 p.m. - 11:44 a.m.MDW-YYC
22h 48m1 stop
C$ 386Multiple Airlines
Find Deal
Mon, 10 Nov - Tue, 18 Nov
Delta Logo
12:30 a.m. - 12:34 p.m.YYC-MDW
11h 04m2 stops
Delta Logo
1:47 p.m. - 8:53 p.m.MDW-YYC
8h 06m1 stop
C$ 392Delta
Find Deal
Mon, 17 Nov - Tue, 25 Nov
WestJet Logo
9:15 a.m. - 5:43 p.m.YEG-MDW
7h 28m1 stop
WestJet Logo
10:40 a.m. - 9:00 p.m.MDW-YEG
11h 20m2 stops
C$ 672WestJet
Find Deal
Wed, 29 Oct - Sat, 1 Nov
WestJet Logo
9:15 a.m. - 5:43 p.m.YEG-MDW
7h 28m1 stop
WestJet Logo
10:40 a.m. - 9:00 p.m.MDW-YEG
11h 20m2 stops
C$ 697WestJet
Find Deal
Wed, 29 Oct - Sat, 1 Nov
Porter Airlines Logo
8:00 a.m. - 10:05 a.m.YEG-MDW
25h 05m2 stops
Porter Airlines Logo
11:00 a.m. - 9:59 p.m.MDW-YEG
11h 59m2 stops
C$ 734Porter Airlines
Find Deal
Tue, 18 Nov - Thu, 20 Nov
Porter Airlines Logo
8:20 a.m. - 10:05 a.m.YYC-MDW
24h 45m2 stops
Porter Airlines Logo
11:00 a.m. - 8:55 p.m.MDW-YYC
10h 55m2 stops
C$ 813Porter Airlines
Find Deal
Thu, 11 Dec - Mon, 15 Dec

Delta flights from Alberta to Chicago Midway Airport

Our best Delta deals on Alberta to Chicago Midway Airport flight tickets
Delta
18 Nov
YYC6:35 a.m.Calgary
5h 32m
1 stop
MDW1:07 p.m.Chicago Midway
25 Nov
MDW1:47 p.m.Chicago Midway
8h 06m
1 stop
YYC8:53 p.m.Calgary
C$ 311
Find similar
Delta
18 Nov
YYC7:45 a.m.Calgary
9h 33m
2 stops
MDW6:18 p.m.Chicago Midway
25 Nov
MDW1:47 p.m.Chicago Midway
8h 06m
1 stop
YYC8:53 p.m.Calgary
C$ 342
Find similar
Delta
17 Nov
YYC12:30 a.m.Calgary
11h 04m
2 stops
MDW12:34 p.m.Chicago Midway
25 Nov
MDW1:47 p.m.Chicago Midway
8h 06m
1 stop
YYC8:53 p.m.Calgary
C$ 392
Find similar

WestJet flights from Alberta to Chicago Midway Airport

Our best WestJet deals on Alberta to Chicago Midway Airport flight tickets
WestJet
29 Oct
YEG9:15 a.m.Edmonton
7h 28m
1 stop
MDW5:43 p.m.Chicago Midway
1 Nov
MDW10:40 a.m.Chicago Midway
11h 20m
2 stops
YEG9:00 p.m.Edmonton
C$ 672
Find similar
WestJet
29 Oct
YEG9:15 a.m.Edmonton
7h 28m
1 stop
MDW5:43 p.m.Chicago Midway
1 Nov
MDW10:40 a.m.Chicago Midway
11h 20m
2 stops
YEG9:00 p.m.Edmonton
C$ 697
Find similar
WestJet
29 Oct
YEG6:00 p.m.Edmonton
14h 45m
2 stops
MDW9:45 a.m.Chicago Midway
1 Nov
MDW10:40 a.m.Chicago Midway
11h 20m
2 stops
YEG9:00 p.m.Edmonton
C$ 715
Find similar

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 6 October 2025.
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 18/11

6:35 a.m.-1:07 p.m.

1 stop5h 32m

Chicago Midway

Tue 25/11

1:47 p.m.-8:53 p.m.

1 stop8h 06m

C$ 311

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 18/11

7:45 a.m.-6:18 p.m.

2 stops9h 33m

Chicago Midway

Tue 25/11

1:47 p.m.-8:53 p.m.

1 stop8h 06m

C$ 342

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Mon 3/11

8:35 p.m.-11:38 a.m.

2 stops14h 03m

Chicago Midway

Mon 10/11

6:15 a.m.-12:11 p.m.

1 stop30h 56m

C$ 365

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 14/11

12:45 a.m.-6:39 p.m.

1 stop16h 54m

Chicago Midway

Wed 19/11

1:56 p.m.-12:11 p.m.

1 stop23h 15m

C$ 368

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 10/11

12:30 a.m.-11:38 a.m.

1 stop10h 08m

Chicago Midway

Tue 18/11

1:56 p.m.-11:44 a.m.

1 stop22h 48m

C$ 386

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 17/11

12:30 a.m.-12:34 p.m.

2 stops11h 04m

Chicago Midway

Tue 25/11

1:47 p.m.-8:53 p.m.

1 stop8h 06m

C$ 392

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 29/10

9:15 a.m.-5:43 p.m.

1 stop7h 28m

Chicago Midway

Sat 1/11

10:40 a.m.-9:00 p.m.

2 stops11h 20m

C$ 672

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 29/10

9:15 a.m.-5:43 p.m.

1 stop7h 28m

Chicago Midway

Sat 1/11

10:40 a.m.-9:00 p.m.

2 stops11h 20m

C$ 697

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Tue 18/11

8:00 a.m.-10:05 a.m.

2 stops25h 05m

Chicago Midway

Thu 20/11

11:00 a.m.-9:59 p.m.

2 stops11h 59m

C$ 734

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 11/12

8:20 a.m.-10:05 a.m.

2 stops24h 45m

Chicago Midway

Mon 15/12

11:00 a.m.-8:55 p.m.

2 stops10h 55m

C$ 813

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

Direct flights

None
There are no direct flights from Alberta to Chicago Midway Airport. There are no popular flight routes from Alberta to Chicago Midway Airport.
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  • 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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