How many flights depart from Calgary to Chicago O'Hare Intl Airport on average per day?

8 flights are operational daily from Calgary to Chicago O'Hare Intl Airport as of August 2026. The most popular departure time for this route is 12:00p.m., with 58% of flights per day taking off in the afternoon.

What is the cheapest airline that flies from Calgary to Chicago O'Hare Intl?

Air Canada, Delta, and WestJet are the most popular carriers operating from Calgary to Chicago O'Hare Intl

How many flights depart from Calgary to Chicago O'Hare Intl Airport on average per week?

61 flights are operational weekly from Calgary to Chicago O'Hare Intl Airport as of August 2026. The most popular departure day for this route is Fri, with 23% of flights per week taking off on this day.

Which airlines fly to Chicago O'Hare Intl Airport?

WestJet, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Calgary according to our data. WestJet is the first choice among our users, with 48% of people opting to fly with this airline when travelling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Calgary Airport to Chicago O'Hare Intl Airport?

Prices for flights from Calgary Airport to Chicago O'Hare Intl Airport were last updated today.

How many operators does momondo search for flights from Calgary Airport to Chicago O'Hare Intl Airport?

As of August 2026, there are 5 operators available to choose from for flights from Calgary Airport to Chicago O'Hare Intl Airport.

How old do you have to be to fly from Calgary Airport to Chicago O'Hare Intl Airport?

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 O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 216 Cheap Flights from Calgary to Chicago O'Hare Intl Airport in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Calgary 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$ 293WestJet

Fri, 25 Sep - Tue, 29 Sep

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$ 293WestJet

Fri, 16 Oct - Sun, 18 Oct

12:30 p.m. - 5:05 p.m.

YYC

ORD

3h 35mdirect

8:40 a.m. - 11:28 a.m.

ORD

YYC

3h 48mdirect

C$ 321United Airlines

Wed, 21 Oct - Sat, 24 Oct

12:37 p.m. - 4:10 p.m.

YYC

ORD

3h 33mdirect

8:40 a.m. - 12:35 p.m.

ORD

YYC

3h 55mdirect

C$ 331United Airlines

Sun, 22 Nov - Sat, 28 Nov

12:30 p.m. - 5:05 p.m.

YYC

ORD

3h 35mdirect

3:40 p.m. - 11:27 p.m.

ORD

YYC

8h 47m

1 stop

C$ 332Multiple Airlines

Wed, 21 Oct - Sat, 24 Oct

1:00 a.m. - 10:15 a.m.

YYC

ORD

8h 15m

1 stop

8:45 a.m. - 3:57 p.m.

ORD

YYC

8h 12m

1 stop

C$ 334Air Canada

Sat, 19 Sep - Tue, 29 Sep

1:00 a.m. - 10:17 a.m.

YYC

ORD

8h 17m

1 stop

8:45 a.m. - 3:57 p.m.

ORD

YYC

8h 12m

1 stop

C$ 343Air Canada

Tue, 20 Oct - Sat, 24 Oct

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

YYC

ORD

3h 40mdirect

3:40 p.m. - 11:47 p.m.

ORD

YYC

9h 07m

1 stop

C$ 349Multiple Airlines

Sun, 20 Sep - Tue, 29 Sep

7:00 a.m. - 11:29 a.m.

YYC

ORD

3h 29mdirect

8:30 p.m. - 11:29 p.m.

ORD

YYC

3h 59mdirect

C$ 353American Airlines

Wed, 23 Sep - Sun, 27 Sep

7:00 a.m. - 11:29 a.m.

YYC

ORD

3h 29mdirect

10:00 a.m. - 12:51 p.m.

ORD

YYC

3h 51mdirect

C$ 358American Airlines

Sat, 3 Oct - Sat, 24 Oct

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WestJet flights from Calgary to Chicago O'Hare Intl Airport

Our best WestJet deals on Calgary to Chicago O'Hare Intl Airport flight tickets

WestJet

25 Sep

YYC12:00 p.m.Calgary

3h 40m

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

29 Sep

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

3h 55m

YYC8:25 p.m.Calgary

C$ 293

WestJet

15 Sep

YYC12:00 p.m.Calgary

3h 40m

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

17 Sep

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

3h 55m

YYC8:25 p.m.Calgary

C$ 294

WestJet

20 Sep

YYC12:00 p.m.Calgary

3h 40m

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

29 Sep

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

3h 55m

YYC8:25 p.m.Calgary

C$ 303

Air Canada flights from Calgary to Chicago O'Hare Intl Airport

Our best Air Canada deals on Calgary to Chicago O'Hare Intl Airport flight tickets

Air Canada

19 Sep

YYC1:00 a.m.Calgary

8h 15m

1 stop

ORD10:15 a.m.Chicago O'Hare Intl

29 Sep

ORD8:45 a.m.Chicago O'Hare Intl

8h 12m

1 stop

YYC3:57 p.m.Calgary

C$ 334

Air Canada

20 Oct

YYC1:00 a.m.Calgary

8h 17m

1 stop

ORD10:17 a.m.Chicago O'Hare Intl

24 Oct

ORD8:45 a.m.Chicago O'Hare Intl

8h 12m

1 stop

YYC3:57 p.m.Calgary

C$ 343

Air Canada

15 Sep

YYC6:00 a.m.Calgary

7h 52m

1 stop

ORD2:52 p.m.Chicago O'Hare Intl

22 Sep

ORD8:45 a.m.Chicago O'Hare Intl

8h 12m

1 stop

YYC3:57 p.m.Calgary

C$ 349

momondo Fare Finder

Use the filters below to find and compare flights from Calgary to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 25/9

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

Nonstop3h 40m

Chicago O'Hare Intl

Tue 29/9

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

Nonstop3h 55m

C$ 293

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 16/10

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

Nonstop3h 40m

Chicago O'Hare Intl

Sun 18/10

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

Nonstop3h 55m

C$ 293

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 21/10

12:30 p.m.-5:05 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Sat 24/10

8:40 a.m.-11:28 a.m.

Nonstop3h 48m

C$ 321

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 22/11

12:37 p.m.-4:10 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Sat 28/11

8:40 a.m.-12:35 p.m.

Nonstop3h 55m

C$ 331

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 21/10

12:30 p.m.-5:05 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Sat 24/10

3:40 p.m.-11:27 p.m.

1 stop8h 47m

C$ 332

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 19/9

1:00 a.m.-10:15 a.m.

1 stop8h 15m

Chicago O'Hare Intl

Tue 29/9

8:45 a.m.-3:57 p.m.

1 stop8h 12m

C$ 334

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 20/10

1:00 a.m.-10:17 a.m.

1 stop8h 17m

Chicago O'Hare Intl

Sat 24/10

8:45 a.m.-3:57 p.m.

1 stop8h 12m

C$ 343

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 20/9

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

Nonstop3h 40m

Chicago O'Hare Intl

Tue 29/9

3:40 p.m.-11:47 p.m.

1 stop9h 07m

C$ 349

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 23/9

7:00 a.m.-11:29 a.m.

Nonstop3h 29m

Chicago O'Hare Intl

Sun 27/9

8:30 p.m.-11:29 p.m.

Nonstop3h 59m

C$ 353

Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 3/10

7:00 a.m.-11:29 a.m.

Nonstop3h 29m

Chicago O'Hare Intl

Sat 24/10

10:00 a.m.-12:51 p.m.

Nonstop3h 51m

C$ 358

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 O'Hare Intl Airport

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 typical price of a round-trip flight between Calgary and Chicago O'Hare Intl Airport?

Prices are currently low for flights on this route.

Typical prices usually range from C$ 374 to C$ 596.
The lowest price recently found on this route was C$ 293.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

In general, November is the cheapest month to fly from Calgary to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 352. The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around C$ 353.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as C$ 635. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago O'Hare Intl Airport for around C$ 1,093.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the morning is the cheapest time of day to fly from Calgary to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 701. Flying to Chicago O'Hare Intl Airport in the morning is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 1,137 on average. Flights to Chicago O'Hare Intl Airport from Calgary at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

What is the cheapest Calgary to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight from Calgary to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 412 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Calgary for as low as C$ 304 on momondo.

What cabin class options are available on Calgary to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Calgary to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Calgary to Chicago O'Hare Intl Airport.

How have Calgary to Chicago O'Hare Intl Airport flight prices changed over time?

As of August 2026, prices for Calgary to Chicago O'Hare Intl Airport flights are approximately 1% more expensive when compared to flights at the same time last year.

When to book flights from Calgary to Chicago O'Hare Intl Airport

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

Estimated round-trip price

Cheap Calgary to Chicago O'Hare Intl Airport (YYC to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago O'Hare Intl Airport

Best price found	C$ 346
Fastest flight time	2h 20m
Direct flights	Every day

The best one-way flight to Chicago O'Hare Intl Airport from Calgary in the past 72 hours is C$ 346. The best round-trip flight deal from Calgary to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 631.

The fastest flight from Calgary to Chicago O'Hare Intl Airport takes 2h 20m

Direct flights go from Calgary to Chicago O'Hare Intl Airport every day.

Search flight deals

Frequently asked questions about flying from Calgary to Chicago O'Hare Intl Airport

How far is Calgary to Chicago O'Hare Intl by plane?
There are 2223.9 km between Calgary and Chicago O'Hare Intl. 2h 20m is a normal flight duration for this route.
When did momondo last update prices for flights from Calgary Airport to Chicago O'Hare Intl Airport?
Prices for flights from Calgary Airport to Chicago O'Hare Intl Airport were last updated today.
How many operators does momondo search for flights from Calgary Airport to Chicago O'Hare Intl Airport?
As of August 2026, there are 5 operators available to choose from for flights from Calgary Airport to Chicago O'Hare Intl Airport.
How old do you have to be to fly from Calgary Airport to Chicago O'Hare Intl Airport?
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 O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Calgary to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Calgary to Chicago O'Hare Intl Airport is Boeing 737-800 (49.82% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (13.49%), Boeing 737 MAX 8 (8.75%), and Boeing 737-700 Passenger/BBJ1 (winglets) (7.08%).
What is the most popular airline from Calgary to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Calgary and Chicago O'Hare Intl Airport, the leading airline is WestJet, making up 46% of the total bookings. Other popular airlines include United Airlines with 18%, American Airlines with 17%, and Air Canada with 15%.

Best airlines flying from Calgary to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Calgary to Chicago O'Hare Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 123	Free Cancellation	Rating 7.1 11,415 reviews	Search Air Canada flights
Delta	PriceFrom C$ 143	Free Cancellation	Rating 7.8 8,497 reviews	Search Delta flights
WestJet	PriceFrom C$ 187	Free Cancellation	Rating 7.2 3,424 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 189	Free Cancellation	Rating 7.4 10,062 reviews	Search United Airlines flights
American Airlines	PriceFrom C$ 199	Free Cancellation	Rating 7.1 11,845 reviews	Search American Airlines flights

Delta Flights From Calgary to Chicago O'Hare Intl Airport
Across 1 Delta flight from Calgary to Chicago O'Hare Intl Airport this week, the average price was C$ 388, with the best Delta deals starting from C$ 143 round-trip. 8,493 users have rated Delta on momondo, with an average score of 7.8/10.
United Airlines Flights From Calgary to Chicago O'Hare Intl Airport
The best United Airlines deal for Calgary to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was C$ 189, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 531 round-trip. United Airlines operates 10 flights out of Calgary into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 10,061 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

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Des Plaines

Merrillville

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Skokie

Tinley Park

Evanston

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Great Lakes

Hammond

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Hoffman Estates

Elmhurst

Valparaiso

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 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 Calgary.

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

Yes momondo offers price alerts on flights to Chicago from Calgary. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago O'Hare Intl Airport trip

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Cheap flights from Calgary to Chicago from C$ 241

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 30/8. 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 Calgary to Chicago O'Hare Intl Airport

Our best WestJet deals on Calgary to Chicago O'Hare Intl Airport flight tickets

Air Canada flights from Calgary to Chicago O'Hare Intl Airport

Our best Air Canada deals on Calgary to Chicago O'Hare Intl Airport flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Calgary to Chicago O'Hare Intl Airport that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Calgary to Chicago O'Hare Intl Airport

What is the typical price of a round-trip flight between Calgary and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest Calgary to Chicago O'Hare Intl flight route?

How far in advance should I book a flight from Calgary to Chicago O'Hare Intl Airport?

What cabin class options are available on Calgary to Chicago O'Hare Intl Airport flights?

Can stopping save me money on Calgary to Chicago O'Hare Intl Airport flights?

How have Calgary to Chicago O'Hare Intl Airport flight prices changed over time?

What is the cheapest airline that flies from Calgary to Chicago O'Hare Intl?

Which airlines fly to Chicago O'Hare Intl Airport?

How many flights depart from Calgary to Chicago O'Hare Intl Airport on average per day?

How many flights depart from Calgary to Chicago O'Hare Intl Airport on average per week?

When to book flights from Calgary to Chicago O'Hare Intl Airport

Cheap Calgary to Chicago O'Hare Intl Airport (YYC to ORD) flight deals and tips

Best price found

Fastest flight time

Direct flights

Frequently asked questions about flying from Calgary to Chicago O'Hare Intl Airport

Best airlines flying from Calgary to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Calgary to Chicago O'Hare Intl Airport with momondo

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago O'Hare Intl Airport 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.

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

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