Which airlines fly to Chicago?

WestJet, Air Canada and United Airlines are the top three most popular airlines that fly to Chicago from Calgary according to our data. WestJet is the first choice among our users, with 39% 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.

Which airport is the most popular layover for flights between Calgary and Chicago?

Ottawa (YOW) was the most common stop: 40% of momondo users choosing one-stop flights on this route connected there.

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

WestJet, Air Canada, and American Airlines are the most popular carriers operating from Calgary to Chicago

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

As of September 2025, there are 11 flights per day flying from Calgary to Chicago. The most common time of day flights depart is 12:00p.m., with 56% of flights taking off in the afternoon.

Which layover airport has the shortest travel time from Calgary to Chicago?

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 7h 51m.

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

78 flights are operational weekly from Calgary to Chicago as of September 2025. The most popular departure day for this route is Thu, with 18% of flights per week taking off on this day.

Which layover airport offers the lowest fares from Calgary to Chicago?

Flights via Ottawa (YOW) offer the lowest average round-trip price of C$ 237.

Which layover airport has the shortest connection time from Calgary to Chicago?

Toronto (YYZ) has the shortest average layover time for this route: 1h 49m.

When did momondo last update prices for flights from Calgary Airport to Chicago?

Prices for flights from Calgary Airport to Chicago are updated daily.

How many operators does momondo search for flights from Calgary Airport to Chicago?

As of September 2025, there are 5 operators available to choose from for flights from Calgary Airport to Chicago.

How old do you have to be to fly from Calgary Airport to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Calgary Airport 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.

C$ 155 Cheap Flights from Calgary to Chicago in 2025

1 adult

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Find the cheapest flights from Calgary to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

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$ 226WestJet

Find Deal

Fri, 17 Oct - Sun, 19 Oct

1:10 a.m. - 9:09 a.m.YYC-ORD

6h 59m1 stop

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

3h 49mdirect

C$ 229

Find Deal

Thu, 16 Oct - Thu, 23 Oct

11:40 p.m. - 9:15 a.m.YYC-ORD

8h 35m1 stop

10:00 a.m. - 6:54 p.m.ORD-YYC

9h 54m1 stop

C$ 231Air Canada

Find Deal

Mon, 27 Oct - Thu, 30 Oct

1:10 a.m. - 9:09 a.m.YYC-ORD

6h 59m1 stop

8:40 a.m. - 3:50 p.m.ORD-YYC

8h 10m1 stop

C$ 236Air Canada

Find Deal

Thu, 16 Oct - Thu, 23 Oct

12:35 p.m. - 5:10 p.m.YYC-ORD

3h 35mdirect

7:10 a.m. - 9:53 p.m.ORD-YYC

15h 43m1 stop

C$ 262United Airlines

Find Deal

Thu, 11 Dec - Mon, 15 Dec

1:29 p.m. - 5:54 p.m.YYC-ORD

3h 25mdirect

9:49 a.m. - 12:34 p.m.ORD-YYC

3h 45mdirect

C$ 266American Airlines

Find Deal

Fri, 24 Oct - Tue, 28 Oct

6:15 a.m. - 11:59 p.m.YYC-ORD

16h 44m1 stop

7:10 a.m. - 9:53 p.m.ORD-YYC

15h 43m1 stop

C$ 270United Airlines

Find Deal

Thu, 11 Dec - Mon, 15 Dec

1:29 p.m. - 5:54 p.m.YYC-ORD

3h 25mdirect

9:45 p.m. - 11:59 a.m.ORD-YYC

15h 14m1 stop

C$ 273American Airlines

Find Deal

Fri, 24 Oct - Tue, 28 Oct

6:45 a.m. - 1:08 p.m.YYC-MDW

5h 23m1 stop

9:20 a.m. - 1:54 p.m.MDW-YYC

5h 34m1 stop

C$ 309Delta

Find Deal

Sat, 25 Oct - Sat, 1 Nov

6:45 a.m. - 5:04 p.m.YYC-ORD

9h 19m1 stop

8:57 a.m. - 1:54 p.m.ORD-YYC

5h 57m1 stop

C$ 312Delta

Find Deal

Sun, 26 Oct - Sat, 1 Nov

American Airlines flights from Calgary to Chicago

Our best American Airlines deals on Calgary to Chicago flight tickets

American Airlines

24 Oct

YYC1:29 p.m.Calgary

3h 25m

ORD5:54 p.m.Chicago O'Hare Intl

28 Oct

ORD9:49 a.m.Chicago O'Hare Intl

3h 45m

YYC12:34 p.m.Calgary

C$ 266

Find similar

American Airlines

24 Oct

YYC1:29 p.m.Calgary

3h 25m

ORD5:54 p.m.Chicago O'Hare Intl

28 Oct

ORD9:45 p.m.Chicago O'Hare Intl

15h 14m

1 stop

YYC11:59 a.m.Calgary

C$ 273

Find similar

American Airlines

30 Sep

YYC6:29 a.m.Calgary

3h 25m

ORD10:54 a.m.Chicago O'Hare Intl

7 Oct

ORD6:45 a.m.Chicago O'Hare Intl

16h 09m

1 stop

YYC9:54 p.m.Calgary

C$ 292

Find similar

Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets

Air Canada

27 Oct

YYC11:40 p.m.Calgary

8h 35m

1 stop

ORD9:15 a.m.Chicago O'Hare Intl

30 Oct

ORD10:00 a.m.Chicago O'Hare Intl

9h 54m

1 stop

YYC6:54 p.m.Calgary

C$ 231

Find similar

Air Canada

16 Oct

YYC1:10 a.m.Calgary

6h 59m

1 stop

ORD9:09 a.m.Chicago O'Hare Intl

23 Oct

ORD8:40 a.m.Chicago O'Hare Intl

8h 10m

1 stop

YYC3:50 p.m.Calgary

C$ 236

Find similar

Air Canada

22 Oct

YYC1:10 a.m.Calgary

7h 41m

1 stop

ORD9:51 a.m.Chicago O'Hare Intl

30 Oct

ORD10:00 a.m.Chicago O'Hare Intl

9h 54m

1 stop

YYC6:54 p.m.Calgary

C$ 237

Find similar

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 17/10

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

Nonstop3h 28m

Chicago O'Hare Intl

Sun 19/10

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

Nonstop3h 49m

C$ 226

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 16/10

1:10 a.m.-9:09 a.m.

1 stop6h 59m

Chicago O'Hare Intl

Thu 23/10

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

Nonstop3h 49m

C$ 229

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 27/10

11:40 p.m.-9:15 a.m.

1 stop8h 35m

Chicago O'Hare Intl

Thu 30/10

10:00 a.m.-6:54 p.m.

1 stop9h 54m

C$ 231

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 16/10

1:10 a.m.-9:09 a.m.

1 stop6h 59m

Chicago O'Hare Intl

Thu 23/10

8:40 a.m.-3:50 p.m.

1 stop8h 10m

C$ 236

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/12

12:35 p.m.-5:10 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 15/12

7:10 a.m.-9:53 p.m.

1 stop15h 43m

C$ 262

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 24/10

1:29 p.m.-5:54 p.m.

Nonstop3h 25m

Chicago O'Hare Intl

Tue 28/10

9:49 a.m.-12:34 p.m.

Nonstop3h 45m

C$ 266

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/12

6:15 a.m.-11:59 p.m.

1 stop16h 44m

Chicago O'Hare Intl

Mon 15/12

7:10 a.m.-9:53 p.m.

1 stop15h 43m

C$ 270

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 24/10

1:29 p.m.-5:54 p.m.

Nonstop3h 25m

Chicago O'Hare Intl

Tue 28/10

9:45 p.m.-11:59 a.m.

1 stop15h 14m

C$ 273

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 25/10

6:45 a.m.-1:08 p.m.

1 stop5h 23m

Chicago Midway

Sat 1/11

9:20 a.m.-1:54 p.m.

1 stop5h 34m

C$ 309

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 26/10

6:45 a.m.-5:04 p.m.

1 stop9h 19m

Chicago O'Hare Intl

Sat 1/11

8:57 a.m.-1:54 p.m.

1 stop5h 57m

C$ 312

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 Calgary 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

Layovers

Other information

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 Calgary averaging around C$ 277.

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$ 688. 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$ 1,011. 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 Calgary to Chicago when you can find flight prices for as low as C$ 366. 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$ 1,493 per ticket.

What is the cheapest Calgary to Chicago flight route?

Fly from Calgary to Chicago O'Hare Intl for the best Calgary - 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 Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 384 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Calgary for as low as C$ 283 on momondo.

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

There are 4 cabin classes available to choose from on Calgary 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 Calgary to Chicago flights?

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

How have Calgary to Chicago flight prices changed over time?

As of September 2025, prices for Calgary to Chicago flights are approximately 13% cheaper when compared to flights at the same time last year.

When to book flights from Calgary to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Calgary to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Calgary to Chicago (YYC to CHI) flight deals and tips

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

Best price found	C$ 278
Fastest flight time	3h 20m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Calgary in the past 72 hours is C$ 278. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is C$ 515.

The fastest flight from Calgary to Chicago takes 3h 20m

Direct flights go from Calgary to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

How far is Calgary to Chicago by plane?
Chicago is 2249.2 km away from Calgary. Flights usually cover this in 3h 25m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Calgary Airport to Chicago?
Prices for flights from Calgary Airport to Chicago are updated daily.
How many operators does momondo search for flights from Calgary Airport to Chicago?
As of September 2025, there are 5 operators available to choose from for flights from Calgary Airport to Chicago.
How old do you have to be to fly from Calgary Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Calgary Airport 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 Calgary to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Calgary to Chicago is Boeing 737-700 (34.41% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (16.88%), Boeing 737-800 Passenger/BBJ2 (winglets) (13.98%), and Airbus A319 (11.85%).
What is the most popular airline from Calgary to Chicago?
Based on momondo bookings for flights between Calgary and Chicago, the leading airline is WestJet, making up 45% of the total bookings. Other popular airlines include Air Canada with 26%, United Airlines with 14%, and American Airlines with 10%.

Best airlines flying from Calgary to Chicago

Compare and see reviews for airlines that fly from Calgary to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 150	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 177	Free Cancellation	Rating 7.2 3,091 reviews	Search WestJet flights
Delta	PriceFrom C$ 185	Free Cancellation	Rating 7.9 7,960 reviews	Search Delta flights
American Airlines	PriceFrom C$ 186	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 253	Free Cancellation	Rating 7.4 8,937 reviews	Search United Airlines flights

Delta Flights From Calgary to Chicago
Delta operates around 1 flight from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 250, but momondo users have found Delta deals from Calgary to Chicago from as low as C$ 133 round-trip. Delta has been scored 7.9/10 in 7,960 reviews.
United Airlines Flights From Calgary to Chicago
The best United Airlines deal for Calgary to Chicago flight tickets found on momondo in the last 72 hours was C$ 183, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 383 round-trip. United Airlines operates 8 flights out of Calgary into Chicago in an average week, so prices vary by time and availability. 8,937 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Munster

Hammond

Merrillville

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Calgary to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. All flights to Chicago from Calgary on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Calgary to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Chicago from Calgary are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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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Sat 11/10

Sat 18/10

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

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Flights to Fort Lauderdalefrom C$ 155

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Flights to New Yorkfrom C$ 226

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Flights to Los Angelesfrom C$ 150

Flights to Miamifrom C$ 312

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Flights to Honolulufrom C$ 262

Flights to Phoenixfrom C$ 173

Flights to Tampafrom C$ 179

Flights to Houstonfrom C$ 248

Flights to Dallasfrom C$ 270

Cheap flights from Calgary to Chicago from C$ 155

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Calgary to Chicago departing on 10/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

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Cheap last-minute flights

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American Airlines flights from Calgary to Chicago

Our best American Airlines deals on Calgary to Chicago flight tickets

Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets

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Use the filters below to find and compare flights from Calgary to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Calgary 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 Calgary averaging around C$ 277.

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 Calgary to Chicago flight route?

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

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

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

There are 4 cabin classes available to choose from on Calgary 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 Calgary to Chicago flights?

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

How have Calgary to Chicago flight prices changed over time?

As of September 2025, prices for Calgary to Chicago flights are approximately 13% cheaper when compared to flights at the same time last year.

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

WestJet, Air Canada, and American Airlines are the most popular carriers operating from Calgary to Chicago

Which airlines fly to Chicago?

Which airport is the most popular layover for flights between Calgary and Chicago?

Ottawa (YOW) was the most common stop: 40% of momondo users choosing one-stop flights on this route connected there.

Which layover airport offers the lowest fares from Calgary to Chicago?

Flights via Ottawa (YOW) offer the lowest average round-trip price of C$ 237.

Which layover airport has the shortest travel time from Calgary to Chicago?

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 7h 51m.

Which layover airport has the shortest connection time from Calgary to Chicago?

Toronto (YYZ) has the shortest average layover time for this route: 1h 49m.

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

As of September 2025, there are 11 flights per day flying from Calgary to Chicago. The most common time of day flights depart is 12:00p.m., with 56% of flights taking off in the afternoon.

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

78 flights are operational weekly from Calgary to Chicago as of September 2025. The most popular departure day for this route is Thu, with 18% of flights per week taking off on this day.

When to book flights from Calgary to Chicago

Cheap Calgary to Chicago (YYC to CHI) flight deals and tips

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

Best price found

Fastest flight time

Direct flights

Airports in Chicago

How far is Calgary to Chicago by plane?

When did momondo last update prices for flights from Calgary Airport to Chicago?

How many operators does momondo search for flights from Calgary Airport to Chicago?

How old do you have to be to fly from Calgary Airport to Chicago?

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

What is the most popular plane model from Calgary to Chicago?

What is the most popular airline from Calgary to Chicago?

Best airlines flying from Calgary to Chicago

Compare and see reviews for airlines that fly from Calgary to Chicago with momondo

Delta Flights From Calgary to Chicago

United Airlines Flights From Calgary to Chicago

Travelling to a place near Chicago?

Why use momondo?

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

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

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

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

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.

Get notified when prices go down

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