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Cheap flights from Alberta to Chicago from $100

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 4/26. 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.
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$182WestJet
Mon, Apr 27 - Fri, May 1
Air Canada Logo
5:35 am - 3:10 pm
YYC
-
ORD
8h 35m
1 stop
Air Canada Logo
3:55 pm - 11:59 pm
ORD
-
YYC
9h 04m
1 stop
$197Air Canada
Sat, Mar 7 - Tue, Mar 10
WestJet Logo
9:10 am - 4:40 pm
YEG
-
ORD
6h 30m
1 stop
WestJet Logo
5:30 pm - 10:55 pm
ORD
-
YEG
6h 25m
1 stop
$209WestJet
Mon, Apr 27 - Fri, May 1
American Airlines Logo
1:40 pm - 6:20 pm
YYC
-
ORD
3h 40mnonstop
American Airlines Logo
5:00 am - 11:44 am
ORD
-
YYC
7h 44m
1 stop
$233American Airlines
Tue, Feb 24 - Tue, Mar 3
Delta Logo
7:15 am - 9:34 pm
YYC
-
ORD
13h 19m
2 stops
Delta Logo
1:55 pm - 11:06 pm
ORD
-
YYC
10h 11m
1 stop
$238Delta
Sat, May 9 - Wed, May 13
Delta Logo
6:30 am - 5:37 pm
YYC
-
MDW
10h 07m
2 stops
Delta Logo
10:49 am - 8:54 pm
MDW
-
YYC
11h 05m
2 stops
$251Delta
Tue, Feb 24 - Tue, Mar 3
United Airlines Logo
3:17 pm - 9:37 am
YEG
-
ORD
17h 20m
1 stop
United Airlines Logo
9:49 pm - 2:08 pm
ORD
-
YEG
17h 19m
1 stop
$267United Airlines
Fri, Apr 10 - Mon, Apr 13
United Airlines Logo
3:17 pm - 12:30 am
YEG
-
ORD
8h 13m
1 stop
United Airlines Logo
9:49 pm - 2:08 pm
ORD
-
YEG
17h 19m
1 stop
$268United Airlines
Fri, Apr 10 - Mon, Apr 13
Multiple Airlines Logo
11:55 pm - 11:50 am
YEG
-
MDW
10h 55m
1 stop
Multiple Airlines Logo
4:15 pm - 2:08 pm
MDW
-
YEG
22h 53m
2 stops
$353Multiple Airlines
Fri, Apr 10 - Mon, Apr 13
Multiple Airlines Logo
6:30 am - 11:51 pm
YEG
-
MDW
16h 21m
2 stops
Multiple Airlines Logo
4:15 pm - 10:28 am
MDW
-
YEG
19h 13m
1 stop
$405Multiple Airlines
Fri, Mar 6 - Sun, Mar 8

Air Canada flights from Alberta to Chicago

Our best Air Canada deals on Alberta to Chicago flight tickets
Air Canada
Mar 7
YYC5:35 amCalgary
8h 35m
1 stop
ORD3:10 pmChicago O'Hare Intl
Mar 10
ORD3:55 pmChicago O'Hare Intl
9h 04m
1 stop
YYC11:59 pmCalgary
$197
Air Canada
Mar 5
YYC5:35 amCalgary
8h 35m
1 stop
ORD3:10 pmChicago O'Hare Intl
Mar 9
ORD3:55 pmChicago O'Hare Intl
9h 04m
1 stop
YYC11:59 pmCalgary
$217
Air Canada
Mar 31
YYC9:00 amCalgary
8h 53m
1 stop
ORD6:53 pmChicago O'Hare Intl
Apr 8
ORD10:43 amChicago O'Hare Intl
10h 15m
1 stop
YYC7:58 pmCalgary
$237

WestJet flights from Alberta to Chicago

Our best WestJet deals on Alberta to Chicago flight tickets
WestJet
Apr 27
YYC12:00 pmCalgary
3h 40m
ORD4:40 pmChicago O'Hare Intl
May 1
ORD5:30 pmChicago O'Hare Intl
3h 55m
YYC8:25 pmCalgary
$182
WestJet
Apr 27
YEG9:10 amEdmonton
6h 30m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 1
ORD5:30 pmChicago O'Hare Intl
6h 25m
1 stop
YEG10:55 pmEdmonton
$209
WestJet
Jul 16
YYC12:15 pmCalgary
3h 28m
ORD4:43 pmChicago O'Hare Intl
Jul 17
ORD5:30 pmChicago O'Hare Intl
3h 49m
YYC8:19 pmCalgary
$216

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 January 29, 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

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 4/27

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Fri 5/1

5:30 pm-8:25 pm

Nonstop3h 55m

$182

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 3/7

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

Tue 3/10

3:55 pm-11:59 pm

1 stop9h 04m

$197

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Mon 4/27

9:10 am-4:40 pm

1 stop6h 30m

Chicago O'Hare Intl

Fri 5/1

5:30 pm-10:55 pm

1 stop6h 25m

$209

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 2/24

1:40 pm-6:20 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 3/3

5:00 am-11:44 am

1 stop7h 44m

$233

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/9

7:15 am-9:34 pm

2 stops13h 19m

Chicago O'Hare Intl

Wed 5/13

1:55 pm-11:06 pm

1 stop10h 11m

$238

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 2/24

6:30 am-5:37 pm

2 stops10h 07m

Chicago Midway

Tue 3/3

10:49 am-8:54 pm

2 stops11h 05m

$251

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 4/10

3:17 pm-9:37 am

1 stop17h 20m

Chicago O'Hare Intl

Mon 4/13

9:49 pm-2:08 pm

1 stop17h 19m

$267

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 4/10

3:17 pm-12:30 am

1 stop8h 13m

Chicago O'Hare Intl

Mon 4/13

9:49 pm-2:08 pm

1 stop17h 19m

$268

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 4/10

11:55 pm-11:50 am

1 stop10h 55m

Chicago Midway

Mon 4/13

4:15 pm-2:08 pm

2 stops22h 53m

$353

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 3/6

6:30 am-11:51 pm

2 stops16h 21m

Chicago Midway

Sun 3/8

4:15 pm-10:28 am

1 stop19h 13m

$405

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 April is, on average, the cheapest month to fly to Chicago from Alberta, with most prices found around $188. If you’re not able to fly to Chicago in April, then November is your next best option. Flight prices from Alberta to Chicago during November average around $209.

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 $179. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Alberta to Chicago for around $467.

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 $346. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $794.

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 $257 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 $162 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

$172

Fastest flight time

3h 28m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Alberta in the past 72 hours is $172. The best round-trip flight deal from Alberta to Chicago found on momondo in the last 72 hours is $185.
The fastest flight from Alberta to Chicago takes 3h 28m
Direct flights go from Alberta to Chicago every day.
There are 3 airports in Chicago. From Alberta there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • 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
10,667 reviews
Search Air Canada flights
WestJetPriceFrom $138Free CancellationRating
7.2
3,253 reviews
Search WestJet flights
United AirlinesPriceFrom $143Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights
American AirlinesPriceFrom $185Free CancellationRating
7.2
11,206 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
Schererville
Valparaiso
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.

An easier way to manage your Chicago trip

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport