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

30 flights are operational weekly from Calgary to Chicago as of November 2025. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.

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 45% 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 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 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?

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

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.

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

Flights via Ottawa (YOW) offer the lowest average round-trip price of C$ 240.

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

As of November 2025, there are 4 flights per day flying from Calgary to Chicago. The most common time of day flights depart is 12:00p.m., with 90% of flights taking off in the afternoon.

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 November 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$ 159 Cheap Flights from Calgary to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Calgary and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from C$ 320 to C$ 795. The lowest price recently found on this route was C$ 227.

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Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

3h 35mdirect

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

3h 55mdirect

C$ 227WestJet

Find Deal

Fri, 5 Dec - Fri, 12 Dec

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

3h 35mdirect

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

3h 55mdirect

C$ 230WestJet

Find Deal

Fri, 13 Mar - Mon, 16 Mar

11:40 p.m. - 9:13 a.m.YYC-ORD

8h 33m1 stop

3:55 p.m. - 12:14 a.m.ORD-YYC

9h 19m1 stop

C$ 279Air Canada

Find Deal

Mon, 24 Nov - Fri, 28 Nov

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

8h 35m1 stop

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

7h 39m1 stop

C$ 286Air Canada

Find Deal

Tue, 2 Dec - Tue, 9 Dec

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

15h 56m1 stop

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

15h 59m1 stop

C$ 289American Airlines

Find Deal

Thu, 4 Dec - Fri, 5 Dec

2:13 p.m. - 9:15 p.m.YYC-ORD

6h 02m1 stop

8:45 a.m. - 11:35 a.m.ORD-YYC

3h 50mdirect

C$ 299United Airlines

Find Deal

Fri, 23 Jan - Tue, 27 Jan

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

16h 44m1 stop

8:45 a.m. - 11:35 a.m.ORD-YYC

3h 50mdirect

C$ 300United Airlines

Find Deal

Mon, 24 Nov - Fri, 28 Nov

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

10h 10m1 stop

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

10h 38m1 stop

C$ 312Delta

Find Deal

Thu, 11 Dec - Mon, 15 Dec

6:35 a.m. - 1:10 p.m.YYC-MDW

5h 35m1 stop

9:34 a.m. - 8:57 p.m.MDW-YYC

12h 23m2 stops

C$ 312Delta

Find Deal

Tue, 2 Dec - Tue, 9 Dec

12:45 p.m. - 8:44 a.m.YYC-ORD

18h 59m1 stop

5:18 a.m. - 11:44 a.m.ORD-YYC

7h 26m1 stop

C$ 314American Airlines

Find Deal

Fri, 14 Nov - Sat, 6 Dec

WestJet flights from Calgary to Chicago

Our best WestJet deals on Calgary 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$ 227

Find similar

WestJet

13 Mar

YYC9:00 a.m.Calgary

3h 35m

ORD1:35 p.m.Chicago O'Hare Intl

16 Mar

ORD2:20 p.m.Chicago O'Hare Intl

3h 55m

YYC5:15 p.m.Calgary

C$ 230

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$ 236

Find similar

Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets

Air Canada

24 Nov

YYC11:40 p.m.Calgary

8h 33m

1 stop

ORD9:13 a.m.Chicago O'Hare Intl

28 Nov

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

9h 19m

1 stop

YYC12:14 a.m.Calgary

C$ 279

Find similar

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

5 Mar

YYC7:10 a.m.Calgary

7h 00m

1 stop

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

8 Mar

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

9h 59m

1 stop

YYC12:54 a.m.Calgary

C$ 309

Find similar

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$ 227

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 13/3

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

Nonstop3h 35m

Chicago O'Hare Intl

Mon 16/3

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

Nonstop3h 55m

C$ 230

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 24/11

11:40 p.m.-9:13 a.m.

1 stop8h 33m

Chicago O'Hare Intl

Fri 28/11

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 279

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

Fri 23/1

2:13 p.m.-9:15 p.m.

1 stop6h 02m

Chicago O'Hare Intl

Tue 27/1

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

C$ 299

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 24/11

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

1 stop16h 44m

Chicago O'Hare Intl

Fri 28/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

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$ 312

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 2/12

6:35 a.m.-1:10 p.m.

1 stop5h 35m

Chicago Midway

Tue 9/12

9:34 a.m.-8:57 p.m.

2 stops12h 23m

C$ 312

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 14/11

12:45 p.m.-8:44 a.m.

1 stop18h 59m

Chicago O'Hare Intl

Sat 6/12

5:18 a.m.-11:44 a.m.

1 stop7h 26m

C$ 314

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 typical price of a round-trip flight between Calgary and Chicago?

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$ 271.

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$ 660. 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$ 999. 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$ 371. 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$ 1,562 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$ 377 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$ 226 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?

You could potentially save up to 2% on your flight if you consider stops on a Calgary to Chicago flight.

How have Calgary to Chicago flight prices changed over time?

As of November 2025, prices for Calgary to Chicago flights are approximately 18% 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$ 375
Fastest flight time	3h 28m
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$ 375. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is C$ 379.

The fastest flight from Calgary to Chicago takes 3h 28m

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 33m, 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 November 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 (26.18% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (15.40%), Airbus A319 (14.80%), and Boeing 737 MAX 8 (14.37%).
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 51% of the total bookings. Other popular airlines include Air Canada with 23%, American Airlines with 12%, and United Airlines with 12%.

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$ 152	Free Cancellation	Rating 7.1 10,403 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 179	Free Cancellation	Rating 7.2 3,153 reviews	Search WestJet flights
Delta	PriceFrom C$ 187	Free Cancellation	Rating 7.9 8,003 reviews	Search Delta flights
American Airlines	PriceFrom C$ 188	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 255	Free Cancellation	Rating 7.4 9,002 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$ 350, but momondo users have found Delta deals from Calgary to Chicago from as low as C$ 187 round-trip. Delta has been scored 7.9/10 in 8,002 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$ 255, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 523 round-trip. United Airlines operates 7 flights out of Calgary into Chicago in an average week, so prices vary by time and availability. 8,998 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.

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Chicago O'Hare Intl Airport

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Flights to Dallasfrom C$ 277

Cheap flights from Calgary to Chicago from C$ 159

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 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.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

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WestJet flights from Calgary to Chicago

Our best WestJet 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 typical price of a round-trip flight between Calgary and Chicago?

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$ 271.

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?

You could potentially save up to 2% on your flight if you consider stops on a Calgary to Chicago flight.

How have Calgary to Chicago flight prices changed over time?

As of November 2025, prices for Calgary to Chicago flights are approximately 18% cheaper when compared to flights at the same time last year.

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

United Airlines, WestJet, and Air Canada 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$ 240.

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 November 2025, there are 4 flights per day flying from Calgary to Chicago. The most common time of day flights depart is 12:00p.m., with 90% of flights taking off in the afternoon.

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

30 flights are operational weekly from Calgary to Chicago as of November 2025. The most popular departure day for this route is Mon, with 20% 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