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 49% 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.

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

Delta, WestJet, and United Airlines 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 3h 34m. Keep in mind that layovers or delays could extend your travel time.

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

8 flights are operational daily from Alberta to Chicago as of May 2026. The most popular departure time for this route is 12:00p.m., with 100% of flights per day taking off in the afternoon.

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

The number of flights available between Alberta and Chicago is 61 per week as of May 2026. The most frequent departure day is Fri, with 18% of weekly flights leaving on this day.

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 May 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$ 183 Cheap Flights from Alberta to Chicago in 2026

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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$ 232WestJet

Mon, 18 May - Sun, 24 May

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$ 235WestJet

Wed, 20 May - Tue, 26 May

6:30 a.m. - 2:55 p.m.

YYC

ORD

7h 25m

1 stop

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

ORD

YYC

3h 55mdirect

C$ 265Multiple Airlines

Thu, 21 May - Sat, 30 May

6:45 a.m. - 5:56 p.m.

YYC

MDW

10h 11m

1 stop

1:59 p.m. - 8:30 p.m.

MDW

YYC

7h 31m

1 stop

C$ 314Delta

Sat, 23 May - Wed, 27 May

6:35 a.m. - 9:46 p.m.

YYC

MDW

14h 11m

2 stops

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

MDW

YYC

18h 06m

2 stops

C$ 347Delta

Sat, 5 Sep - Wed, 9 Sep

4:50 p.m. - 12:44 a.m.

YEG

ORD

6h 54m

1 stop

5:00 a.m. - 2:08 p.m.

ORD

YEG

10h 08m

1 stop

C$ 412United Airlines

Wed, 3 Jun - Wed, 10 Jun

3:42 p.m. - 8:16 p.m.

YEG

ORD

3h 34mdirect

7:05 a.m. - 10:04 p.m.

ORD

YEG

15h 59m

1 stop

C$ 415United Airlines

Wed, 17 Jun - Sat, 20 Jun

12:30 a.m. - 11:09 a.m.

YYC

MDW

9h 39m

1 stop

5:37 p.m. - 2:45 p.m.

MDW

YYC

22h 08m

2 stops

C$ 516Multiple Airlines

Tue, 19 May - Sat, 6 Jun

12:55 a.m. - 9:00 a.m.

YMM

ORD

7h 05m

1 stop

8:40 p.m. - 3:47 p.m.

ORD

YMM

20h 07m

2 stops

C$ 603Air Canada

Wed, 23 Sep - Fri, 25 Sep

12:55 a.m. - 9:00 a.m.

YMM

ORD

7h 05m

1 stop

8:40 p.m. - 3:47 p.m.

ORD

YMM

20h 07m

2 stops

C$ 605Air Canada

Wed, 23 Sep - Fri, 25 Sep

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WestJet flights from Alberta to Chicago

Our best WestJet deals on Alberta to Chicago flight tickets

WestJet

18 May

YYC12:00 p.m.Calgary

3h 40m

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

24 May

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

3h 55m

YYC8:25 p.m.Calgary

C$ 232

WestJet

20 May

YYC12:00 p.m.Calgary

3h 40m

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

26 May

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

3h 55m

YYC8:25 p.m.Calgary

C$ 235

WestJet

18 May

YYC12:00 p.m.Calgary

3h 40m

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

24 May

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

3h 55m

YYC8:25 p.m.Calgary

C$ 236

Delta flights from Alberta to Chicago

Our best Delta deals on Alberta to Chicago flight tickets

Delta

20 May

YYC7:45 a.m.Calgary

10h 05m

1 stop

ORD6:50 p.m.Chicago O'Hare Intl

26 May

ORD12:30 p.m.Chicago O'Hare Intl

9h 00m

1 stop

YYC8:30 p.m.Calgary

C$ 314

Delta

23 May

YYC6:45 a.m.Calgary

9h 06m

1 stop

ORD4:51 p.m.Chicago O'Hare Intl

27 May

ORD3:47 p.m.Chicago O'Hare Intl

5h 43m

1 stop

YYC8:30 p.m.Calgary

C$ 330

Delta

5 Aug

YYC7:45 a.m.Calgary

10h 12m

1 stop

ORD6:57 p.m.Chicago O'Hare Intl

10 Aug

ORD1:55 p.m.Chicago O'Hare Intl

10h 11m

1 stop

YYC11:06 p.m.Calgary

C$ 337

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 18/5

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

Nonstop3h 40m

Chicago O'Hare Intl

Sun 24/5

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

Nonstop3h 55m

C$ 232

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 20/5

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

Nonstop3h 40m

Chicago O'Hare Intl

Tue 26/5

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

Nonstop3h 55m

C$ 235

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 21/5

6:30 a.m.-2:55 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Sat 30/5

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

Nonstop3h 55m

C$ 265

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 23/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

Chicago Midway

Wed 27/5

1:59 p.m.-8:30 p.m.

1 stop7h 31m

C$ 314

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 5/9

6:35 a.m.-9:46 p.m.

2 stops14h 11m

Chicago Midway

Wed 9/9

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

2 stops18h 06m

C$ 347

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Wed 3/6

4:50 p.m.-12:44 a.m.

1 stop6h 54m

Chicago O'Hare Intl

Wed 10/6

5:00 a.m.-2:08 p.m.

1 stop10h 08m

C$ 412

EdmontonChicago

YEG - ORD

YEGORD

Edmonton

Wed 17/6

3:42 p.m.-8:16 p.m.

Nonstop3h 34m

Chicago O'Hare Intl

Sat 20/6

7:05 a.m.-10:04 p.m.

1 stop15h 59m

C$ 414

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 19/5

12:30 a.m.-11:09 a.m.

1 stop9h 39m

Chicago Midway

Sat 6/6

5:37 p.m.-2:45 p.m.

2 stops22h 08m

C$ 516

Fort McMurrayChicago

YMM - ORD

YMMORD

Fort Mcmurray

Wed 23/9

12:55 a.m.-9:00 a.m.

1 stop7h 05m

Chicago O'Hare Intl

Fri 25/9

8:40 p.m.-3:47 p.m.

2 stops20h 07m

C$ 603

Fort McMurrayChicago

YMM - ORD

YMMORD

Fort Mcmurray

Wed 23/9

12:55 a.m.-9:00 a.m.

1 stop7h 05m

Chicago O'Hare Intl

Fri 25/9

8:40 p.m.-3:47 p.m.

2 stops20h 07m

C$ 605

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 September is another great option to travel to Chicago, with average flight prices from Alberta averaging around C$ 87.

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$ 1,081. 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$ 696. 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$ 1,326 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 from Alberta 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$ 383 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$ 295 on momondo.

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$ 288
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$ 288. The best round-trip flight deal from Alberta to Chicago found on momondo in the last 72 hours is C$ 471.

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

Frequently asked questions about flying from Alberta to Chicago

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 May 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 737-800, representing 24.88% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 18.13%, Boeing 737-700 at 15.46%, and Boeing 737 MAX 8 at 11.14%.

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 Canada	PriceFrom C$ 119	Free Cancellation	Rating 7.1 10,993 reviews	Search Air Canada flights
Delta	PriceFrom C$ 146	Free Cancellation	Rating 7.9 8,460 reviews	Search Delta flights
United Airlines	PriceFrom C$ 165	Free Cancellation	Rating 7.4 9,683 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 181	Free Cancellation	Rating 7.2 3,331 reviews	Search WestJet flights
American Airlines	PriceFrom C$ 193	Free Cancellation	Rating 7.1 11,674 reviews	Search American Airlines flights

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Munster

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.

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Cheap flights from Alberta to Chicago from C$ 183

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 21/5. 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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WestJet flights from Alberta to Chicago

Our best WestJet deals on Alberta to Chicago flight tickets

Delta flights from Alberta to Chicago

Our best Delta deals on Alberta to Chicago flight tickets

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How to get the cheapest flight ticket from Alberta to Chicago

What is the cheapest month to fly to Chicago?

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

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

What is the cheapest Alberta to Chicago flight route?

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

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

Which airlines fly to Chicago?

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

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

How long does it take to fly 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

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago 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.

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Daily price changes in your inbox - only with Price Alerts.

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

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Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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