Cheap flights from Alberta to Chicago from $115

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 5/10. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$195WestJet
Thu, Apr 30 - Thu, May 7
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$211WestJet
Sun, Apr 26 - Thu, Apr 30
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$214WestJet
Mon, Apr 20 - Mon, Apr 27
United Airlines Logo
1:27 pm - 12:30 am
YYC
-
ORD
10h 03m
1 stop
United Airlines Logo
8:42 am - 11:32 am
ORD
-
YYC
3h 50mnonstop
$227United Airlines
Fri, Apr 17 - Tue, Apr 21
United Airlines Logo
6:00 am - 9:20 pm
YYC
-
ORD
14h 20m
1 stop
United Airlines Logo
10:04 pm - 1:53 pm
ORD
-
YYC
16h 49m
1 stop
$237United Airlines
Fri, Apr 17 - Mon, Apr 20
Air Canada Logo
5:35 am - 3:15 pm
YYC
-
ORD
8h 40m
1 stop
Air Canada Logo
4:15 pm - 12:23 am
ORD
-
YYC
9h 08m
1 stop
$238Air Canada
Fri, Apr 17 - Tue, Apr 21
Multiple Airlines Logo
7:00 am - 10:19 pm
YYC
-
MDW
14h 19m
1 stop
Multiple Airlines Logo
6:10 am - 5:10 pm
MDW
-
YYC
12h 00m
1 stop
$323Multiple Airlines
Mon, Apr 27 - Wed, Apr 29
Delta Logo
9:15 am - 10:28 pm
YEG
-
MDW
12h 13m
2 stops
Delta Logo
9:29 am - 4:55 pm
MDW
-
YEG
8h 26m
1 stop
$327Delta
Mon, Apr 20 - Mon, Apr 27
Multiple Airlines Logo
12:30 am - 9:58 am
YYC
-
MDW
8h 28m
1 stop
Multiple Airlines Logo
6:10 am - 5:10 pm
MDW
-
YYC
12h 00m
1 stop
$336Multiple Airlines
Sat, Apr 25 - Wed, Apr 29
Delta Logo
9:40 am - 6:36 pm
YEG
-
MDW
7h 56m
1 stop
Delta Logo
9:29 am - 4:55 pm
MDW
-
YEG
8h 26m
1 stop
$340Delta
Wed, Apr 29 - Wed, May 6

American Airlines flights from Alberta to Chicago

Our best American Airlines deals on Alberta to Chicago flight tickets
American Airlines
Sep 3
YYC6:29 amCalgary
3h 25m
ORD10:54 amChicago O'Hare Intl
Sep 6
ORD8:34 pmChicago O'Hare Intl
3h 55m
YYC11:29 pmCalgary
$278
American Airlines
May 20
YYC6:45 amCalgary
16h 03m
1 stop
ORD11:48 pmChicago O'Hare Intl
Jun 1
ORD8:50 pmChicago O'Hare Intl
3h 48m
YYC11:38 pmCalgary
$298
American Airlines
Sep 8
YYC6:29 amCalgary
3h 25m
ORD10:54 amChicago O'Hare Intl
Sep 9
ORD8:25 pmChicago O'Hare Intl
3h 55m
YYC11:20 pmCalgary
$300

Air Canada flights from Alberta to Chicago

Our best Air Canada deals on Alberta to Chicago flight tickets
Air Canada
Apr 17
YYC5:35 amCalgary
8h 40m
1 stop
ORD3:15 pmChicago O'Hare Intl
Apr 21
ORD4:15 pmChicago O'Hare Intl
9h 08m
1 stop
YYC12:23 amCalgary
$238
Air Canada
Apr 28
YYC7:00 amCalgary
7h 15m
1 stop
ORD3:15 pmChicago O'Hare Intl
May 5
ORD3:50 pmChicago O'Hare Intl
8h 08m
1 stop
YYC10:58 pmCalgary
$241
Air Canada
Apr 27
YYC11:40 pmCalgary
8h 30m
1 stop
ORD9:10 amChicago O'Hare Intl
May 4
ORD8:20 pmChicago O'Hare Intl
14h 11m
1 stop
YYC9:31 amCalgary
$242

momondo Fare Finder

 
Customize your flight search to find flights from Alberta to Chicago 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 832,500 searches. Data last updated March 16, 2026.
Use the filters below to find and compare flights from Alberta to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 4/30

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Thu 5/7

5:30 pm-8:25 pm

Nonstop3h 55m

$195

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 4/26

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-8:25 pm

Nonstop3h 55m

$211
Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 4/20

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 4/27

5:30 pm-8:25 pm

Nonstop3h 55m

$214

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 4/17

1:27 pm-12:30 am

1 stop10h 03m

Chicago O'Hare Intl

Tue 4/21

8:42 am-11:32 am

Nonstop3h 50m

$227

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 4/17

6:00 am-9:20 pm

1 stop14h 20m

Chicago O'Hare Intl

Mon 4/20

10:04 pm-1:53 pm

1 stop16h 49m

$237

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 4/17

5:35 am-3:15 pm

1 stop8h 40m

Chicago O'Hare Intl

Tue 4/21

4:15 pm-12:23 am

1 stop9h 08m

$238

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 4/27

7:00 am-10:19 pm

1 stop14h 19m

Chicago Midway

Wed 4/29

6:10 am-5:10 pm

1 stop12h 00m

$323

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Mon 4/20

9:15 am-10:28 pm

2 stops12h 13m

Chicago Midway

Mon 4/27

9:29 am-4:55 pm

1 stop8h 26m

$327

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 4/25

12:30 am-9:58 am

1 stop8h 28m

Chicago Midway

Wed 4/29

6:10 am-5:10 pm

1 stop12h 00m

$336

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 4/29

9:40 am-6:36 pm

1 stop7h 56m

Chicago Midway

Wed 5/6

9:29 am-4:55 pm

1 stop8h 26m

$340

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

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

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Alberta, with most prices found around $189. If you’re not able to fly to Chicago in November, then January is your next best option. Flight prices from Alberta to Chicago during January average around $192.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as $262. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Alberta to Chicago for around $485.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Alberta to Chicago during this time can be as low as $350. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $846.

What is the cheapest Alberta to Chicago flight route?

Fly from Calgary to Chicago O'Hare Intl for the best Alberta - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Alberta when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $269 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Alberta for as low as $214 on momondo.

What cabin class options are available on Alberta to Chicago flights?

There are 4 cabin classes available to choose from on Alberta to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Alberta to Chicago flights?

No. A direct flight is the cheapest option for a flight between Alberta to Chicago.

Cheap Alberta to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Alberta to Chicago

Best Price Found

$210

Fastest flight time

3h 27m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Alberta in the past 72 hours is $210. The best round-trip flight deal from Alberta to Chicago found on momondo in the last 72 hours is $266.
The fastest flight from Alberta to Chicago takes 3h 27m
Direct flights go from Alberta to Chicago on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is American Airlines.
There are 3 airports in Chicago. From Alberta there are direct flights to Chicago O'Hare Intl (ORD).
  • When did momondo last update prices for flights from Alberta to Chicago?

    Prices for flights from Alberta to Chicago refresh daily.

  • How many operators does momondo search for flights from Alberta to Chicago?

  • How old do you have to be to fly from Alberta to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Alberta to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Alberta to Chicago?

Best airlines flying from Alberta to Chicago

Compare and see reviews for airlines that fly from Alberta to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $83Free CancellationRating
7.1
10,806 reviews
Search Air Canada flights
WestJetPriceFrom $137Free CancellationRating
7.2
3,295 reviews
Search WestJet flights
United AirlinesPriceFrom $143Free CancellationRating
7.4
9,429 reviews
Search United Airlines flights
American AirlinesPriceFrom $185Free CancellationRating
7.1
11,466 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Alberta to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Alberta to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Alberta to Chicago with flexible booking policies on momondo?

All flight searches from Alberta to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Alberta to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Alberta to Chicago.

I’m not ready to book a flight from Alberta to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Alberta and alert you when they change.

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1 adult
Wed 4/15
Wed 4/22

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago