What is the most punctual flight time for Chicago to Calgary flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

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

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

How often are flights from Chicago to Calgary delayed?

Historically, on average around 27% of flights between Chicago and Calgary have experienced a delay on any given week. The average delay length over the past 12 months has been 142 minutes.

What airlines fly to Calgary?

WestJet, American Airlines and United Airlines are the top three most popular airlines that fly to Calgary from Chicago according to our data. WestJet is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Calgary. Keep in mind that there are 5 different airlines that fly to Calgary on a routine basis, so you have a few additional options to choose from.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Calgary flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.

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

The number of flights available between Chicago and Calgary is 2 per day as of November 2025. The most frequent departure time is 8:00AM, with 84% of daily flights leaving at noon.

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

16 flights are operational weekly from Chicago to Calgary as of November 2025. The most popular departure day for this route is Mon, with 25% of flights per week taking off on this day.

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

Prices for flights from Chicago to Calgary Airport refresh daily.

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

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

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

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 Chicago to Calgary Airport.

What documentation or ID do you need to fly to Calgary Airport?

The travel and health documents required for your trip to Calgary 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 Calgary Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$56 Cheap Flights from Chicago to Calgary in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from $203 to $590. The lowest price recently found on this route was $145.

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2:20 pm - 5:15 pmORD-YYC

3h 55mnonstop

9:00 am - 1:35 pmYYC-ORD

3h 35mnonstop

$145WestJet

Find Deal

Fri, Jan 30 - Fri, Feb 6

2:20 pm - 5:15 pmORD-YYC

3h 55mnonstop

9:00 am - 1:35 pmYYC-ORD

3h 35mnonstop

$147WestJet

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Mon, Jan 19 - Mon, Jan 26

2:20 pm - 5:15 pmORD-YYC

3h 55mnonstop

9:00 am - 1:35 pmYYC-ORD

3h 35mnonstop

$153WestJet

Find Deal

Fri, Feb 27 - Mon, Mar 2

5:30 pm - 8:19 pmORD-YYC

3h 49mnonstop

12:15 pm - 4:43 pmYYC-ORD

3h 28mnonstop

$154WestJet

Find Deal

Sat, May 9 - Tue, May 12

5:30 pm - 8:19 pmORD-YYC

3h 49mnonstop

12:15 pm - 4:43 pmYYC-ORD

3h 28mnonstop

$155WestJet

Find Deal

Sat, May 16 - Wed, May 27

2:20 pm - 5:15 pmORD-YYC

3h 55mnonstop

9:00 am - 1:35 pmYYC-ORD

3h 35mnonstop

$161WestJet

Find Deal

Fri, Jan 16 - Fri, Jan 23

4:19 pm - 9:51 pmMDW-YYC

30h 32m1 stop

9:45 pm - 12:05 pmYYC-MDW

13h 20m2 stops

$226Multiple Airlines

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Mon, Jan 19 - Mon, Jan 26

1:49 pm - 8:54 pmMDW-YYC

8h 05m1 stop

6:30 am - 1:06 pmYYC-MDW

5h 36m1 stop

$251Delta

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Wed, Jan 28 - Wed, Feb 11

1:50 pm - 8:57 pmMDW-YYC

8h 07m1 stop

6:35 am - 1:10 pmYYC-MDW

5h 35m1 stop

$255Delta

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Wed, Dec 10 - Sat, Dec 13

1:49 pm - 8:54 pmMDW-YYC

8h 05m1 stop

6:30 am - 5:55 pmYYC-MDW

10h 25m2 stops

$260Delta

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Wed, Jan 28 - Wed, Feb 11

WestJet flights from Chicago to Calgary

Our best WestJet deals on Chicago to Calgary flight tickets

WestJet

Jan 30

ORD2:20 pmChicago O'Hare Intl

3h 55m

YYC5:15 pmCalgary

Feb 6

YYC9:00 amCalgary

3h 35m

ORD1:35 pmChicago O'Hare Intl

$145

Find similar

WestJet

Jan 19

ORD2:20 pmChicago O'Hare Intl

3h 55m

YYC5:15 pmCalgary

Jan 26

YYC9:00 amCalgary

3h 35m

ORD1:35 pmChicago O'Hare Intl

$147

Find similar

WestJet

Feb 27

ORD2:20 pmChicago O'Hare Intl

3h 55m

YYC5:15 pmCalgary

Mar 2

YYC9:00 amCalgary

3h 35m

ORD1:35 pmChicago O'Hare Intl

$153

Find similar

United Airlines flights from Chicago to Calgary

Our best United Airlines deals on Chicago to Calgary flight tickets

United Airlines

May 5

ORD9:00 amChicago O'Hare Intl

3h 54m

YYC11:54 amCalgary

May 12

YYC12:30 pmCalgary

3h 20m

ORD4:50 pmChicago O'Hare Intl

$185

Find similar

United Airlines

Feb 3

ORD5:40 amChicago O'Hare Intl

8h 28m

1 stop

YYC1:08 pmCalgary

Feb 10

YYC12:37 pmCalgary

3h 31m

ORD5:08 pmChicago O'Hare Intl

$190

Find similar

United Airlines

May 16

ORD7:15 amChicago O'Hare Intl

15h 23m

1 stop

YYC9:38 pmCalgary

May 29

YYC8:30 amCalgary

3h 20m

ORD12:50 pmChicago O'Hare Intl

$195

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 1/30

2:20 pm-5:15 pm

Nonstop3h 55m

Calgary

Fri 2/6

9:00 am-1:35 pm

Nonstop3h 35m

$145

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 1/19

2:20 pm-5:15 pm

Nonstop3h 55m

Calgary

Mon 1/26

9:00 am-1:35 pm

Nonstop3h 35m

$147

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 2/27

2:20 pm-5:15 pm

Nonstop3h 55m

Calgary

Mon 3/2

9:00 am-1:35 pm

Nonstop3h 35m

$153

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 5/9

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Tue 5/12

12:15 pm-4:43 pm

Nonstop3h 28m

$154

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 5/16

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Wed 5/27

12:15 pm-4:43 pm

Nonstop3h 28m

$155

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 1/16

2:20 pm-5:15 pm

Nonstop3h 55m

Calgary

Fri 1/23

9:00 am-1:35 pm

Nonstop3h 35m

$161

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 1/19

4:19 pm-9:51 pm

1 stop30h 32m

Calgary

Mon 1/26

9:45 pm-12:05 pm

2 stops13h 20m

$226

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 1/28

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Wed 2/11

6:30 am-1:06 pm

1 stop5h 36m

$251

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 12/10

1:50 pm-8:57 pm

1 stop8h 07m

Calgary

Sat 12/13

6:35 am-1:10 pm

1 stop5h 35m

$255

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 1/28

1:49 pm-8:54 pm

1 stop8h 05m

Calgary

Wed 2/11

6:30 am-5:55 pm

2 stops10h 25m

$260

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How to get the cheapest flight ticket from Chicago to Calgary

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

Delays

Other information

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

What is the cheapest month to fly to Calgary?

The month of October is, on average, the cheapest month to fly to Calgary from Chicago, with most prices found around $213. If you aren’t able to travel during the month of October, then book flights to Calgary from Chicago during May instead. Flights to Calgary in May, while not as cheap as those in October, still average around $220.

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

The cheapest day to depart on your flight to Calgary is on a Thursday when prices can be found for as low as $291. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago to Calgary on a Tuesday will generally be more expensive and average around $327. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

The cheapest time of day to fly to Calgary is in the afternoon when flights can be purchased for as low as $263. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $480 on average. Flights to Calgary from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Calgary flight route?

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

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

You are more likely to see cheaper flights to Calgary from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Calgary for around $274 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Calgary from Chicago for as low as $231 on momondo.

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

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

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

How have Chicago to Calgary flight prices changed over time?

As of November 2025, prices for Chicago to Calgary flights are approximately 44% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Calgary

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

Estimated round-trip price

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

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

Best Price Found	$85
Fastest flight time	3h 42m
Direct flights	Every day
Airports in Calgary	1 airport

The best one-way flight to Calgary from Chicago in the past 72 hours is $85. The best round-trip flight deal from Chicago to Calgary found on momondo in the last 72 hours is $240.

The fastest flight from Chicago to Calgary takes 3h 42m

Direct flights go from Chicago to Calgary every day.

There is 1 airport near Calgary: Calgary (YYC)

Search flight deals

How far is Chicago to Calgary by plane?
Chicago and Calgary are 1397.6 mi apart from one another. Flights usually cover this in 3h 49m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Calgary Airport?
Prices for flights from Chicago to Calgary Airport refresh daily.
How many operators does momondo search for flights from Chicago to Calgary Airport?
As of November 2025, there are 5 operators available to choose from for flights from Chicago to Calgary Airport.
How old do you have to be to fly from Chicago to Calgary Airport?
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 Chicago to Calgary Airport.
What documentation or ID do you need to fly to Calgary Airport?
The travel and health documents required for your trip to Calgary 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 Calgary 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 Chicago to Calgary?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Calgary is Boeing 737-700, representing 30.95% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 14.79%, Airbus A319 at 13.96%, and Boeing 737-800 at 12.34%.
What is the most popular airline from Chicago to Calgary?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Calgary is WestJet (45% of total bookings). The next most popular airlines are American Airlines (22%), United Airlines (15%), and Delta (12%).

Best airlines flying from Chicago to Calgary

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

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom $91	Free Cancellation	Rating 7.1 10,466 reviews	Search Air Canada flights
United Airlines	PriceFrom $91	Free Cancellation	Rating 7.4 9,039 reviews	Search United Airlines flights
Delta	PriceFrom $109	Free Cancellation	Rating 7.9 7,993 reviews	Search Delta flights
WestJet	PriceFrom $142	Free Cancellation	Rating 7.2 3,172 reviews	Search WestJet flights
American Airlines	PriceFrom $198	Free Cancellation	Rating 7.2 11,043 reviews	Search American Airlines flights

Delta Flights From Chicago to Calgary
Across 2 Delta flights from Chicago to Calgary this week, the average price was $294, with the best Delta deals starting from $109 round-trip. 7,998 users have rated Delta on momondo, with an average score of 7.9/10.
United Airlines Flights From Chicago to Calgary
United Airlines is also a popular choice for this route. United Airlines flight deals for Chicago to Calgary start from as low as $91 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $338. United Airlines operates 6 flights to Calgary from Chicago in an average week. Users have rated it 7.4/10 across 9,044 reviews.

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Why use momondo?

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

Finding the right flight to Calgary from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Calgary quick and easy, saving you time and money.

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

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

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

momondo helps you find the best flight between Chicago and Calgary by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Chicago to Calgary flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Cheap flights from Chicago to Calgary from $56

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Calgary departing on 2/20. 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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How to get the cheapest flight ticket from Chicago to Calgary

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 Chicago and Calgary?

What is the cheapest month to fly to Calgary?

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

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

What is the cheapest Chicago to Calgary flight route?

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

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

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

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

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

How have Chicago to Calgary flight prices changed over time?

As of November 2025, prices for Chicago to Calgary flights are approximately 44% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Calgary?

How often are flights from Chicago to Calgary delayed?

Historically, on average around 27% of flights between Chicago and Calgary have experienced a delay on any given week. The average delay length over the past 12 months has been 142 minutes.

What is the most punctual flight time for Chicago to Calgary flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Calgary flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.

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

The number of flights available between Chicago and Calgary is 2 per day as of November 2025. The most frequent departure time is 8:00AM, with 84% of daily flights leaving at noon.

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

16 flights are operational weekly from Chicago to Calgary as of November 2025. The most popular departure day for this route is Mon, with 25% of flights per week taking off on this day.

When to book flights from Chicago to Calgary

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Calgary

How far is Chicago to Calgary by plane?

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

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

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

What documentation or ID do you need to fly to Calgary Airport?

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

What is the most popular airline from Chicago to Calgary?

Best airlines flying from Chicago to Calgary

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

Delta Flights From Chicago to Calgary

United Airlines Flights From Chicago to Calgary

Traveling to a place near Calgary?

Why use momondo?

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

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

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

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

An easier way to manage your Calgary 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.