Which airlines fly to Chicago?

WestJet, United Airlines and Air Canada are the top three most popular airlines that fly to Chicago from Alberta according to our data. WestJet is the first choice among our users, with 50% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Alberta to Chicago on average per week?

The number of flights available between Alberta and Chicago is 39 per week as of January 2026. The most frequent departure day is Wed, with 18% of weekly flights leaving on this day.

What is the cheapest airline that flies from Alberta to Chicago?

United Airlines, WestJet, and Air Canada are the most popular carriers operating from Alberta to Chicago

How long does it take to fly to Chicago?

Flight times from Alberta to Chicago vary, but if you’re flying out of Calgary and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 3h 27m on average. Another popular route from Alberta to Chicago is flying from Edmonton to Chicago O'Hare Intl Airport, which will take roughly 6h 35m. Keep in mind that layovers or delays could extend your travel time.

How many flights depart from Alberta to Chicago on average per day?

5 flights are operational daily from Alberta to Chicago as of January 2026. The most popular departure time for this route is 12:00p.m., with 94% of flights per day taking off in the afternoon.

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?

As of January 2026, there are 5 operators available to choose from 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.

C$ 136 Cheap Flights from Alberta to Chicago in 2026

1 adult

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Find the cheapest flights from Alberta to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:00 p.m. - 4:40 p.m.

YYC

ORD

3h 40mdirect

5:30 p.m. - 8:25 p.m.

ORD

YYC

3h 55mdirect

C$ 247WestJet

Mon, 27 Apr - Fri, 1 May

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

YYC

ORD

8h 35m

1 stop

3:55 p.m. - 11:59 p.m.

ORD

YYC

9h 04m

1 stop

C$ 267Air Canada

Sat, 7 Mar - Tue, 10 Mar

12:15 p.m. - 4:43 p.m.

YYC

ORD

3h 28mdirect

5:30 p.m. - 8:19 p.m.

ORD

YYC

3h 49mdirect

C$ 293WestJet

Thu, 16 Jul - Fri, 17 Jul

1:40 p.m. - 6:20 p.m.

YYC

ORD

3h 40mdirect

5:00 a.m. - 11:44 a.m.

ORD

YYC

7h 44m

1 stop

C$ 316American Airlines

Tue, 24 Feb - Tue, 3 Mar

6:35 a.m. - 4:48 p.m.

YYC

ORD

9h 13m

1 stop

1:55 p.m. - 11:06 p.m.

ORD

YYC

10h 11m

1 stop

C$ 323Delta

Sat, 9 May - Mon, 11 May

6:30 a.m. - 5:37 p.m.

YYC

MDW

10h 07m

2 stops

10:49 a.m. - 8:54 p.m.

MDW

YYC

11h 05m

2 stops

C$ 341Delta

Tue, 24 Feb - Tue, 3 Mar

3:17 p.m. - 9:37 a.m.

YEG

ORD

17h 20m

1 stop

9:49 p.m. - 2:08 p.m.

ORD

YEG

17h 19m

1 stop

C$ 362United Airlines

Fri, 10 Apr - Mon, 13 Apr

3:17 p.m. - 9:37 a.m.

YEG

ORD

17h 20m

1 stop

9:49 p.m. - 2:08 p.m.

ORD

YEG

17h 19m

1 stop

C$ 372United Airlines

Fri, 10 Apr - Mon, 13 Apr

9:15 a.m. - 1:25 p.m.

YEG

MDW

27h 10m

1 stop

6:00 a.m. - 10:47 p.m.

MDW

YEG

17h 47m

2 stops

C$ 658Multiple Airlines

Fri, 13 Mar - Tue, 17 Mar

5:50 p.m. - 8:54 a.m.

YEG

MDW

14h 04m

2 stops

11:05 a.m. - 4:50 p.m.

MDW

YEG

30h 45m

1 stop

C$ 660Multiple Airlines

Sat, 14 Feb - Tue, 17 Feb

Air Canada flights from Alberta to Chicago

Our best Air Canada deals on Alberta to Chicago flight tickets

Air Canada

7 Mar

YYC5:35 a.m.Calgary

8h 35m

1 stop

ORD3:10 p.m.Chicago O'Hare Intl

10 Mar

ORD3:55 p.m.Chicago O'Hare Intl

9h 04m

1 stop

YYC11:59 p.m.Calgary

C$ 267

Air Canada

5 Mar

YYC5:35 a.m.Calgary

8h 35m

1 stop

ORD3:10 p.m.Chicago O'Hare Intl

9 Mar

ORD3:55 p.m.Chicago O'Hare Intl

9h 04m

1 stop

YYC11:59 p.m.Calgary

C$ 295

Air Canada

31 Mar

YYC9:00 a.m.Calgary

8h 53m

1 stop

ORD6:53 p.m.Chicago O'Hare Intl

8 Apr

ORD10:43 a.m.Chicago O'Hare Intl

10h 15m

1 stop

YYC7:58 p.m.Calgary

C$ 322

WestJet flights from Alberta to Chicago

Our best WestJet deals on Alberta to Chicago flight tickets

WestJet

27 Apr

YYC12:00 p.m.Calgary

3h 40m

ORD4:40 p.m.Chicago O'Hare Intl

1 May

ORD5:30 p.m.Chicago O'Hare Intl

3h 55m

YYC8:25 p.m.Calgary

C$ 247

WestJet

16 Jul

YYC12:15 p.m.Calgary

3h 28m

ORD4:43 p.m.Chicago O'Hare Intl

17 Jul

ORD5:30 p.m.Chicago O'Hare Intl

3h 49m

YYC8:19 p.m.Calgary

C$ 293

WestJet

29 Jun

YYC12:15 p.m.Calgary

3h 28m

ORD4:43 p.m.Chicago O'Hare Intl

7 Jul

ORD5:30 p.m.Chicago O'Hare Intl

3h 49m

YYC8:19 p.m.Calgary

C$ 296

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 27/4

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Fri 1/5

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 247

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 7/3

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

1 stop8h 35m

Chicago O'Hare Intl

Tue 10/3

3:55 p.m.-11:59 p.m.

1 stop9h 04m

C$ 267

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 16/7

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Fri 17/7

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 293

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 24/2

1:40 p.m.-6:20 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Tue 3/3

5:00 a.m.-11:44 a.m.

1 stop7h 44m

C$ 316

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 9/5

6:35 a.m.-4:48 p.m.

1 stop9h 13m

Chicago O'Hare Intl

Mon 11/5

1:55 p.m.-11:06 p.m.

1 stop10h 11m

C$ 323

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 24/2

6:30 a.m.-5:37 p.m.

2 stops10h 07m

Chicago Midway

Tue 3/3

10:49 a.m.-8:54 p.m.

2 stops11h 05m

C$ 341

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 10/4

3:17 p.m.-9:37 a.m.

1 stop17h 20m

Chicago O'Hare Intl

Mon 13/4

9:49 p.m.-2:08 p.m.

1 stop17h 19m

C$ 362

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Fri 10/4

3:17 p.m.-9:37 a.m.

1 stop17h 20m

Chicago O'Hare Intl

Mon 13/4

9:49 p.m.-2:08 p.m.

1 stop17h 19m

C$ 372

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 13/3

9:15 a.m.-1:25 p.m.

1 stop27h 10m

Chicago Midway

Tue 17/3

6:00 a.m.-10:47 p.m.

2 stops17h 47m

C$ 658

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Sat 14/2

5:50 p.m.-8:54 a.m.

2 stops14h 04m

Chicago Midway

Tue 17/2

11:05 a.m.-4:50 p.m.

1 stop30h 45m

C$ 660

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of November is another great option to travel to Chicago, with average flight prices from Alberta averaging around C$ 284.

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$ 591. 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 Sunday because tickets tend to average around C$ 975. 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 morning is the cheapest time of day to fly from Alberta to Chicago when you can find flight prices for as low as C$ 711. Flying to Chicago in the morning 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$ 1,405 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$ 349 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$ 220 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$ 230
Fastest flight time	3h 27m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Alberta in the past 72 hours is C$ 230. The best round-trip flight deal from Alberta to Chicago found on momondo in the last 72 hours is C$ 525.

The fastest flight from Alberta to Chicago takes 3h 27m

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 are updated daily.
How many operators does momondo search for flights from Alberta to Chicago?
As of January 2026, there are 5 operators available to choose from 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?
momondo data reveals that the most frequently booked plane model on the route from Alberta to Chicago is Boeing 737-700, representing 24.27% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 21.72%, Boeing 737-700 Passenger/BBJ1 (winglets) at 17.48%, and Airbus A319 at 10.07%.

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
Delta	PriceFrom C$ 144	Free Cancellation	Rating 7.9 8,127 reviews	Search Delta flights
Air Canada	PriceFrom C$ 146	Free Cancellation	Rating 7.1 10,667 reviews	Search Air Canada flights
American Airlines	PriceFrom C$ 168	Free Cancellation	Rating 7.2 11,206 reviews	Search American Airlines flights
WestJet	PriceFrom C$ 172	Free Cancellation	Rating 7.2 3,253 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 175	Free Cancellation	Rating 7.4 9,215 reviews	Search United Airlines flights

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.