Latest deals
Insights
FAQs
Price Alerts

Cheap flights from Alberta to Chicago from C$ 170

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 12/12. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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. - 1:09 p.m.YYC-MDW
5h 39m1 stop
Delta Logo
1:49 p.m. - 8:54 p.m.MDW-YYC
8h 05m1 stop
C$ 311Delta
Find Deal
Thu, 15 Jan - Tue, 20 Jan
Multiple Airlines Logo
7:30 a.m. - 11:44 p.m.YYC-MDW
15h 14m1 stop
Multiple Airlines Logo
9:13 a.m. - 7:09 p.m.MDW-YYC
10h 56m1 stop
C$ 328Multiple Airlines
Find Deal
Fri, 16 Jan - Sun, 18 Jan
Multiple Airlines Logo
7:35 p.m. - 11:47 a.m.YYC-MDW
15h 12m1 stop
Multiple Airlines Logo
12:57 p.m. - 10:52 p.m.MDW-YYC
10h 55m1 stop
C$ 346Multiple Airlines
Find Deal
Thu, 15 Jan - Mon, 19 Jan
Multiple Airlines Logo
9:45 p.m. - 6:12 p.m.YYC-MDW
19h 27m2 stops
Multiple Airlines Logo
8:42 p.m. - 11:44 a.m.MDW-YYC
16h 02m1 stop
C$ 348Multiple Airlines
Find Deal
Sat, 13 Dec - Mon, 15 Dec
Delta Logo
6:35 a.m. - 6:00 p.m.YYC-MDW
10h 25m2 stops
Delta Logo
9:34 a.m. - 8:57 p.m.MDW-YYC
12h 23m2 stops
C$ 365Delta
Find Deal
Tue, 9 Dec - Tue, 16 Dec
Multiple Airlines Logo
8:55 a.m. - 11:25 p.m.YYC-MDW
13h 30m1 stop
Multiple Airlines Logo
12:50 p.m. - 12:05 a.m.MDW-YYC
12h 15m1 stop
C$ 366Multiple Airlines
Find Deal
Thu, 19 Feb - Sat, 21 Feb
Delta Logo
7:15 a.m. - 9:45 p.m.YYC-MDW
13h 30m2 stops
Delta Logo
10:35 a.m. - 11:06 p.m.MDW-YYC
13h 31m2 stops
C$ 384Delta
Find Deal
Tue, 14 Apr - Thu, 16 Apr
Multiple Airlines Logo
8:55 a.m. - 10:13 p.m.YYC-MDW
12h 18m1 stop
Multiple Airlines Logo
9:13 a.m. - 7:09 p.m.MDW-YYC
10h 56m1 stop
C$ 387Multiple Airlines
Find Deal
Sat, 17 Jan - Sun, 18 Jan
Delta Logo
12:30 a.m. - 9:51 a.m.YYC-MDW
8h 21m1 stop
Delta Logo
9:20 a.m. - 11:06 p.m.MDW-YYC
14h 46m2 stops
C$ 394Delta
Find Deal
Mon, 13 Apr - Thu, 16 Apr
Delta Logo
7:00 a.m. - 6:05 p.m.YYC-MDW
10h 05m2 stops
Delta Logo
6:00 a.m. - 11:06 p.m.MDW-YYC
18h 06m2 stops
C$ 395Delta
Find Deal
Tue, 14 Apr - Thu, 16 Apr

Delta flights from Alberta to Chicago Midway Airport

Our best Delta deals on Alberta to Chicago Midway Airport flight tickets
Delta
15 Jan
YYC6:30 a.m.Calgary
5h 39m
1 stop
MDW1:09 p.m.Chicago Midway
20 Jan
MDW1:49 p.m.Chicago Midway
8h 05m
1 stop
YYC8:54 p.m.Calgary
C$ 311
Find similar
Delta
9 Dec
YYC6:35 a.m.Calgary
10h 25m
2 stops
MDW6:00 p.m.Chicago Midway
16 Dec
MDW9:34 a.m.Chicago Midway
12h 23m
2 stops
YYC8:57 p.m.Calgary
C$ 365
Find similar
Delta
14 Apr
YYC7:15 a.m.Calgary
13h 30m
2 stops
MDW9:45 p.m.Chicago Midway
16 Apr
MDW10:35 a.m.Chicago Midway
13h 31m
2 stops
YYC11:06 p.m.Calgary
C$ 384
Find similar

WestJet flights from Alberta to Chicago Midway Airport

Our best WestJet deals on Alberta to Chicago Midway Airport flight tickets
WestJet
13 Feb
YEG6:00 p.m.Edmonton
15h 15m
2 stops
MDW10:15 a.m.Chicago Midway
18 Feb
MDW9:50 a.m.Chicago Midway
12h 05m
2 stops
YEG8:55 p.m.Edmonton
C$ 752
Find similar
WestJet
24 Dec
YEG9:15 a.m.Edmonton
7h 04m
1 stop
MDW5:19 p.m.Chicago Midway
31 Dec
MDW5:59 p.m.Chicago Midway
23h 00m
1 stop
YEG3:59 p.m.Edmonton
C$ 771
Find similar
WestJet
16 Dec
YEG6:30 a.m.Edmonton
26h 24m
2 stops
MDW9:54 a.m.Chicago Midway
23 Dec
MDW5:59 p.m.Chicago Midway
23h 00m
1 stop
YEG3:59 p.m.Edmonton
C$ 794
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 19 November 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

Thu 15/1

6:30 a.m.-1:09 p.m.

1 stop5h 39m

Chicago Midway

Tue 20/1

1:49 p.m.-8:54 p.m.

1 stop8h 05m

C$ 311

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 16/1

7:30 a.m.-11:44 p.m.

1 stop15h 14m

Chicago Midway

Sun 18/1

9:13 a.m.-7:09 p.m.

1 stop10h 56m

C$ 328

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 15/1

7:35 p.m.-11:47 a.m.

1 stop15h 12m

Chicago Midway

Mon 19/1

12:57 p.m.-10:52 p.m.

1 stop10h 55m

C$ 346

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 13/12

9:45 p.m.-6:12 p.m.

2 stops19h 27m

Chicago Midway

Mon 15/12

8:42 p.m.-11:44 a.m.

1 stop16h 02m

C$ 348

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/12

6:35 a.m.-6:00 p.m.

2 stops10h 25m

Chicago Midway

Tue 16/12

9:34 a.m.-8:57 p.m.

2 stops12h 23m

C$ 365

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 19/2

8:55 a.m.-11:25 p.m.

1 stop13h 30m

Chicago Midway

Sat 21/2

12:50 p.m.-12:05 a.m.

1 stop12h 15m

C$ 366

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 14/4

7:15 a.m.-9:45 p.m.

2 stops13h 30m

Chicago Midway

Thu 16/4

10:35 a.m.-11:06 p.m.

2 stops13h 31m

C$ 384

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 17/1

8:55 a.m.-10:13 p.m.

1 stop12h 18m

Chicago Midway

Sun 18/1

9:13 a.m.-7:09 p.m.

1 stop10h 56m

C$ 387

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 13/4

12:30 a.m.-9:51 a.m.

1 stop8h 21m

Chicago Midway

Thu 16/4

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

2 stops14h 46m

C$ 394

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 14/4

7:00 a.m.-6:05 p.m.

2 stops10h 05m

Chicago Midway

Thu 16/4

6:00 a.m.-11:06 p.m.

2 stops18h 06m

C$ 395

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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.
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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 19/12
Fri 26/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago