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Cheap flights from Alberta to Chicago from C$ 197

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 16/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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. - 1:32 p.m.
YYC
-
MDW
5h 52m
1 stop
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 377Delta
Sat, 2 May - Tue, 5 May
Delta Logo
7:40 a.m. - 10:28 p.m.
YYC
-
MDW
13h 48m
2 stops
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 446Delta
Sat, 2 May - Tue, 5 May
Delta Logo
7:45 a.m. - 5:56 p.m.
YYC
-
MDW
9h 11m
2 stops
Delta Logo
9:22 a.m. - 10:15 p.m.
MDW
-
YYC
13h 53m
2 stops
C$ 449Delta
Sat, 9 May - Sat, 16 May
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
9:23 a.m. - 10:57 p.m.
MDW
-
YYC
14h 34m
2 stops
C$ 452Delta
Wed, 20 May - Sun, 24 May
Multiple Airlines Logo
8:00 p.m. - 11:09 a.m.
YYC
-
MDW
14h 09m
2 stops
Multiple Airlines Logo
12:04 p.m. - 11:00 a.m.
MDW
-
YYC
23h 56m
1 stop
C$ 453Multiple Airlines
Mon, 4 May - Wed, 6 May
Delta Logo
7:40 a.m. - 10:28 p.m.
YYC
-
MDW
13h 48m
2 stops
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 456Delta
Sat, 2 May - Tue, 5 May
Multiple Airlines Logo
7:00 a.m. - 11:09 a.m.
YYC
-
MDW
27h 09m
1 stop
Multiple Airlines Logo
12:04 p.m. - 11:00 a.m.
MDW
-
YYC
23h 56m
1 stop
C$ 457Multiple Airlines
Mon, 4 May - Wed, 6 May
Multiple Airlines Logo
12:30 a.m. - 7:31 p.m.
YYC
-
MDW
18h 01m
1 stop
Multiple Airlines Logo
6:10 a.m. - 5:10 p.m.
MDW
-
YYC
12h 00m
1 stop
C$ 480Multiple Airlines
Sun, 26 Apr - Wed, 29 Apr
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
Delta Logo
9:17 a.m. - 8:38 p.m.
MDW
-
YYC
12h 21m
2 stops
C$ 483Delta
Mon, 25 May - Fri, 12 Jun
Delta Logo
9:40 a.m. - 6:36 p.m.
YEG
-
MDW
7h 56m
1 stop
Delta Logo
9:23 a.m. - 4:55 p.m.
MDW
-
YEG
8h 32m
1 stop
C$ 507Delta
Wed, 6 May - Sat, 9 May

Porter Airlines flights from Alberta to Chicago Midway Airport

Our best Porter Airlines deals on Alberta to Chicago Midway Airport flight tickets
Porter Airlines
4 May
YYC7:00 a.m.Calgary
25h 45m
3 stops
MDW9:45 a.m.Chicago Midway
6 May
MDW10:30 a.m.Chicago Midway
12h 56m
2 stops
YYC10:26 p.m.Calgary
C$ 646
Porter Airlines
28 May
YEG7:00 a.m.Edmonton
25h 45m
3 stops
MDW9:45 a.m.Chicago Midway
4 Jun
MDW10:25 a.m.Chicago Midway
12h 05m
2 stops
YEG9:30 p.m.Edmonton
C$ 721
Porter Airlines
28 May
YEG11:50 a.m.Edmonton
20h 55m
2 stops
MDW9:45 a.m.Chicago Midway
4 Jun
MDW10:25 a.m.Chicago Midway
12h 05m
2 stops
YEG9:30 p.m.Edmonton
C$ 767

Delta flights from Alberta to Chicago Midway Airport

Our best Delta deals on Alberta to Chicago Midway Airport flight tickets
Delta
2 May
YYC6:40 a.m.Calgary
5h 52m
1 stop
MDW1:32 p.m.Chicago Midway
5 May
MDW9:27 a.m.Chicago Midway
12h 13m
2 stops
YYC8:40 p.m.Calgary
C$ 377
Delta
2 May
YYC7:40 a.m.Calgary
13h 48m
2 stops
MDW10:28 p.m.Chicago Midway
5 May
MDW9:27 a.m.Chicago Midway
12h 13m
2 stops
YYC8:40 p.m.Calgary
C$ 446
Delta
9 May
YYC7:45 a.m.Calgary
9h 11m
2 stops
MDW5:56 p.m.Chicago Midway
16 May
MDW9:22 a.m.Chicago Midway
13h 53m
2 stops
YYC10:15 p.m.Calgary
C$ 449

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 15 April 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

Sat 2/5

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$ 377

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/5

7:40 a.m.-10:28 p.m.

2 stops13h 48m

Chicago Midway

Tue 5/5

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

2 stops12h 13m

C$ 446

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 9/5

7:45 a.m.-5:56 p.m.

2 stops9h 11m

Chicago Midway

Sat 16/5

9:22 a.m.-10:15 p.m.

2 stops13h 53m

C$ 449

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 20/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Sun 24/5

9:23 a.m.-10:57 p.m.

2 stops14h 34m

C$ 452

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 4/5

8:00 p.m.-11:09 a.m.

2 stops14h 09m

Chicago Midway

Wed 6/5

12:04 p.m.-11:00 a.m.

1 stop23h 56m

C$ 453

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 2/5

7:40 a.m.-10:28 p.m.

2 stops13h 48m

Chicago Midway

Tue 5/5

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

2 stops12h 13m

C$ 456

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 4/5

7:00 a.m.-11:09 a.m.

1 stop27h 09m

Chicago Midway

Wed 6/5

12:04 p.m.-11:00 a.m.

1 stop23h 56m

C$ 457

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 26/4

12:30 a.m.-7:31 p.m.

1 stop18h 01m

Chicago Midway

Wed 29/4

6:10 a.m.-5:10 p.m.

1 stop12h 00m

C$ 480

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 25/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Fri 12/6

9:17 a.m.-8:38 p.m.

2 stops12h 21m

C$ 483
Quickest round-trip

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 6/5

9:40 a.m.-6:36 p.m.

1 stop7h 56m

Chicago Midway

Sat 9/5

9:23 a.m.-4:55 p.m.

1 stop8h 32m

C$ 507

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 34m

Direct flights

None
The fastest flight from Alberta to Chicago Midway Airport takes 5h 34m
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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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 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
Merrillville
Hammond
Munster

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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