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Cheap flights from Alberta to Chicago from C$ 158

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 29/1. 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
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
C$ 221WestJet
Find Deal
Fri, 5 Dec - Fri, 12 Dec
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
C$ 227WestJet
Find Deal
Fri, 5 Dec - Fri, 12 Dec
Multiple Airlines Logo
5:35 a.m. - 3:10 p.m.YYC-ORD
8h 35m1 stop
Multiple Airlines Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
C$ 270Multiple Airlines
Find Deal
Fri, 5 Dec - Fri, 12 Dec
Multiple Airlines Logo
12:30 a.m. - 3:12 p.m.YYC-ORD
13h 42m1 stop
Multiple Airlines Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
C$ 275Multiple Airlines
Find Deal
Mon, 1 Dec - Mon, 5 Jan
Air Canada Logo
5:35 a.m. - 3:10 p.m.YYC-ORD
8h 35m1 stop
Air Canada Logo
2:00 p.m. - 8:39 p.m.ORD-YYC
7h 39m1 stop
C$ 286Air Canada
Find Deal
Tue, 2 Dec - Tue, 9 Dec
American Airlines Logo
6:30 a.m. - 11:26 p.m.YYC-ORD
15h 56m1 stop
American Airlines Logo
8:45 p.m. - 11:44 a.m.ORD-YYC
15h 59m1 stop
C$ 289American Airlines
Find Deal
Thu, 4 Dec - Fri, 5 Dec
Delta Logo
7:35 a.m. - 6:45 p.m.YYC-ORD
10h 10m1 stop
Delta Logo
1:50 p.m. - 11:02 p.m.ORD-YYC
10h 12m1 stop
C$ 300Delta
Find Deal
Tue, 16 Dec - Sun, 11 Jan
Delta Logo
7:35 a.m. - 6:45 p.m.YYC-ORD
10h 10m1 stop
Delta Logo
1:35 p.m. - 11:13 p.m.ORD-YYC
10h 38m1 stop
C$ 311Delta
Find Deal
Thu, 11 Dec - Mon, 15 Dec
Air Canada Logo
12:55 a.m. - 11:18 a.m.YEG-ORD
9h 23m1 stop
Air Canada Logo
3:55 p.m. - 12:43 a.m.ORD-YEG
9h 48m1 stop
C$ 318Air Canada
Find Deal
Wed, 3 Dec - Wed, 10 Dec
American Airlines Logo
1:13 p.m. - 5:45 p.m.YYC-ORD
3h 32mdirect
American Airlines Logo
9:40 a.m. - 12:22 p.m.ORD-YYC
3h 42mdirect
C$ 453American Airlines
Find Deal
Mon, 13 Apr - Fri, 17 Apr

Air Canada flights from Alberta to Chicago

Our best Air Canada deals on Alberta to Chicago flight tickets
Air Canada
2 Dec
YYC5:35 a.m.Calgary
8h 35m
1 stop
ORD3:10 p.m.Chicago O'Hare Intl
9 Dec
ORD2:00 p.m.Chicago O'Hare Intl
7h 39m
1 stop
YYC8:39 p.m.Calgary
C$ 286
Find similar
Air Canada
3 Dec
YEG12:55 a.m.Edmonton
9h 23m
1 stop
ORD11:18 a.m.Chicago O'Hare Intl
10 Dec
ORD3:55 p.m.Chicago O'Hare Intl
9h 48m
1 stop
YEG12:43 a.m.Edmonton
C$ 318
Find similar
Air Canada
3 Dec
YEG12:55 a.m.Edmonton
9h 23m
1 stop
ORD11:18 a.m.Chicago O'Hare Intl
10 Dec
ORD3:55 p.m.Chicago O'Hare Intl
8h 20m
1 stop
YEG11:15 p.m.Edmonton
C$ 328
Find similar

WestJet flights from Alberta to Chicago

Our best WestJet deals on Alberta to Chicago flight tickets
WestJet
5 Dec
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
12 Dec
ORD2:20 p.m.Chicago O'Hare Intl
3h 55m
YYC5:15 p.m.Calgary
C$ 221
Find similar
WestJet
5 Dec
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
12 Dec
ORD2:20 p.m.Chicago O'Hare Intl
3h 55m
YYC5:15 p.m.Calgary
C$ 227
Find similar
WestJet
13 Apr
YYC9:00 a.m.Calgary
3h 35m
ORD1:35 p.m.Chicago O'Hare Intl
17 Apr
ORD2:20 p.m.Chicago O'Hare Intl
3h 55m
YYC5:15 p.m.Calgary
C$ 282
Find similar

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 96,600 searches. Data last updated 3 November 2025.
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

Fri 5/12

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Fri 12/12

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 221

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/12

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Fri 12/12

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 227

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/12

5:35 a.m.-3:10 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Fri 12/12

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 270

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 1/12

12:30 a.m.-3:12 p.m.

1 stop13h 42m

Chicago O'Hare Intl

Mon 5/1

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 275

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 2/12

5:35 a.m.-3:10 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Tue 9/12

2:00 p.m.-8:39 p.m.

1 stop7h 39m

C$ 286

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 4/12

6:30 a.m.-11:26 p.m.

1 stop15h 56m

Chicago O'Hare Intl

Fri 5/12

8:45 p.m.-11:44 a.m.

1 stop15h 59m

C$ 289

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 16/12

7:35 a.m.-6:45 p.m.

1 stop10h 10m

Chicago O'Hare Intl

Sun 11/1

1:50 p.m.-11:02 p.m.

1 stop10h 12m

C$ 300

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/12

7:35 a.m.-6:45 p.m.

1 stop10h 10m

Chicago O'Hare Intl

Mon 15/12

1:35 p.m.-11:13 p.m.

1 stop10h 38m

C$ 311

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Wed 3/12

12:55 a.m.-11:18 a.m.

1 stop9h 23m

Chicago O'Hare Intl

Wed 10/12

3:55 p.m.-12:43 a.m.

1 stop9h 48m

C$ 318

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 13/4

1:13 p.m.-5:45 p.m.

Nonstop3h 32m

Chicago O'Hare Intl

Fri 17/4

9:40 a.m.-12:22 p.m.

Nonstop3h 42m

C$ 452

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 February is another great option to travel to Chicago, with average flight prices from Alberta averaging around C$ 270.

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 Friday when prices can be found for as low as C$ 659. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 997. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the afternoon is the cheapest time of day to fly from Alberta to Chicago when you can find flight prices for as low as C$ 370. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,559 per ticket.

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 C$ 377 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 C$ 226 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

C$ 374

Fastest flight time

3h 20m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Alberta in the past 72 hours is C$ 374. The best round-trip flight deal from Alberta to Chicago found on momondo in the last 72 hours is C$ 378.
The fastest flight from Alberta to Chicago takes 3h 20m
Direct flights go from Alberta to Chicago every day.
There is 1 airport near Chicago: 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 are updated 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?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Alberta to Chicago.

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

    The travel and health documents you'll need for your trip to Chicago 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. It is always advisable to seek advice from your airline or a trusted 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 C$ 151Free CancellationRating
7.1
10,398 reviews
Search Air Canada flights
WestJetPriceFrom C$ 179Free CancellationRating
7.2
3,153 reviews
Search WestJet flights
DeltaPriceFrom C$ 187Free CancellationRating
7.9
8,002 reviews
Search Delta flights
American AirlinesPriceFrom C$ 188Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 225Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights

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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Alberta to Chicago for you.

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

Flights from Alberta to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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?

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 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport