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Cheap flights from Alberta to Chicago from C$ 217

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 5/9. 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 a.m. - 9:45 p.m.
YYC
-
MDW
13h 00m
2 stops
Delta Logo
6:00 a.m. - 11:13 p.m.
MDW
-
YYC
18h 13m
2 stops
C$ 365Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 9:45 p.m.
YYC
-
MDW
13h 00m
2 stops
Delta Logo
6:00 a.m. - 11:13 p.m.
MDW
-
YYC
18h 13m
2 stops
C$ 367Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 4:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 11:13 p.m.
MDW
-
YYC
11h 43m
2 stops
C$ 441Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 9:45 p.m.
YYC
-
MDW
13h 00m
2 stops
Delta Logo
12:30 p.m. - 8:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 443Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 4:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
6:00 a.m. - 11:13 p.m.
MDW
-
YYC
18h 13m
2 stops
C$ 451Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
7:45 a.m. - 4:50 p.m.
YYC
-
MDW
8h 05m
1 stop
Delta Logo
12:30 p.m. - 8:54 p.m.
MDW
-
YYC
9h 24m
1 stop
C$ 472Delta
Fri, 30 Oct - Mon, 2 Nov
Delta Logo
7:00 a.m. - 4:15 p.m.
YYC
-
MDW
8h 15m
1 stop
Delta Logo
1:51 p.m. - 8:35 p.m.
MDW
-
YYC
7h 44m
1 stop
C$ 483Delta
Wed, 12 Aug - Mon, 17 Aug
Porter Airlines Logo
11:50 a.m. - 9:40 a.m.
YEG
-
MDW
20h 50m
2 stops
Porter Airlines Logo
10:25 a.m. - 11:24 a.m.
MDW
-
YEG
25h 59m
1 stop
C$ 698Porter Airlines
Sat, 4 Jul - Sat, 11 Jul
Porter Airlines Logo
11:50 p.m. - 2:35 p.m.
YEG
-
MDW
13h 45m
1 stop
Porter Airlines Logo
10:25 a.m. - 11:24 a.m.
MDW
-
YEG
25h 59m
1 stop
C$ 750Porter Airlines
Sun, 28 Jun - Sun, 5 Jul
Multiple Airlines Logo
12:55 a.m. - 2:35 p.m.
YEG
-
MDW
12h 40m
1 stop
Multiple Airlines Logo
10:25 a.m. - 9:35 p.m.
MDW
-
YEG
12h 10m
2 stops
C$ 763Multiple Airlines
Mon, 13 Jul - Sun, 19 Jul

Delta flights from Alberta to Chicago Midway Airport

Our best Delta deals on Alberta to Chicago Midway Airport flight tickets
Delta
29 Oct
YYC7:45 a.m.Calgary
13h 00m
2 stops
MDW9:45 p.m.Chicago Midway
2 Nov
MDW6:00 a.m.Chicago Midway
18h 13m
2 stops
YYC11:13 p.m.Calgary
C$ 365
Delta
29 Oct
YYC7:45 a.m.Calgary
13h 00m
2 stops
MDW9:45 p.m.Chicago Midway
2 Nov
MDW6:00 a.m.Chicago Midway
18h 13m
2 stops
YYC11:13 p.m.Calgary
C$ 367
Delta
29 Oct
YYC7:45 a.m.Calgary
8h 05m
1 stop
MDW4:50 p.m.Chicago Midway
2 Nov
MDW12:30 p.m.Chicago Midway
11h 43m
2 stops
YYC11:13 p.m.Calgary
C$ 441

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 Jul
YEG11:50 a.m.Edmonton
20h 50m
2 stops
MDW9:40 a.m.Chicago Midway
11 Jul
MDW10:25 a.m.Chicago Midway
25h 59m
1 stop
YEG11:24 a.m.Edmonton
C$ 698
Porter Airlines
28 Jun
YEG11:50 p.m.Edmonton
13h 45m
1 stop
MDW2:35 p.m.Chicago Midway
5 Jul
MDW10:25 a.m.Chicago Midway
25h 59m
1 stop
YEG11:24 a.m.Edmonton
C$ 750
Porter Airlines
4 Jul
YEG11:50 a.m.Edmonton
20h 50m
2 stops
MDW9:40 a.m.Chicago Midway
11 Jul
MDW10:25 a.m.Chicago Midway
25h 59m
1 stop
YEG11:24 a.m.Edmonton
C$ 785

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 3 June 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 29/10

7:45 a.m.-9:45 p.m.

2 stops13h 00m

Chicago Midway

Mon 2/11

6:00 a.m.-11:13 p.m.

2 stops18h 13m

C$ 365

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

7:45 a.m.-9:45 p.m.

2 stops13h 00m

Chicago Midway

Mon 2/11

6:00 a.m.-11:13 p.m.

2 stops18h 13m

C$ 367

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Mon 2/11

12:30 p.m.-11:13 p.m.

2 stops11h 43m

C$ 441

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

7:45 a.m.-9:45 p.m.

2 stops13h 00m

Chicago Midway

Mon 2/11

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 443

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Mon 2/11

6:00 a.m.-11:13 p.m.

2 stops18h 13m

C$ 451

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 30/10

7:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Mon 2/11

12:30 p.m.-8:54 p.m.

1 stop9h 24m

C$ 472
Quickest round-trip

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 12/8

7:00 a.m.-4:15 p.m.

1 stop8h 15m

Chicago Midway

Mon 17/8

1:51 p.m.-8:35 p.m.

1 stop7h 44m

C$ 483

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sat 4/7

11:50 a.m.-9:40 a.m.

2 stops20h 50m

Chicago Midway

Sat 11/7

10:25 a.m.-11:24 a.m.

1 stop25h 59m

C$ 698

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sun 28/6

11:50 p.m.-2:35 p.m.

1 stop13h 45m

Chicago Midway

Sun 5/7

10:25 a.m.-11:24 a.m.

1 stop25h 59m

C$ 750

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Mon 13/7

12:55 a.m.-2:35 p.m.

1 stop12h 40m

Chicago Midway

Sun 19/7

10:25 a.m.-9:35 p.m.

2 stops12h 10m

C$ 763

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

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.
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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

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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