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 offers the lowest fares from Calgary to Chicago?

Flights via Ottawa (YOW) offer the lowest average round-trip price of C$ 242.

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

WestJet, United Airlines, and Delta 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.

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

As of November 2025, there are 3 flights per day flying from Calgary to Chicago. The most common time of day flights depart is 12:00p.m., with 92% of flights taking off in the afternoon.

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 46% 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.

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

26 flights are operational weekly from Calgary to Chicago as of November 2025. The most popular departure day for this route is Mon, with 23% of flights per week taking off on this day.

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$ 124 Cheap Flights from Calgary to Chicago in 2025/26

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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.

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$ 206WestJet

Find Deal

Mon, 26 Jan - Fri, 30 Jan

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$ 238WestJet

Find Deal

Mon, 20 Apr - Fri, 24 Apr

11:40 p.m. - 9:10 a.m.YYC-ORD

8h 30m1 stop

8:40 a.m. - 4:14 p.m.ORD-YYC

8h 34m1 stop

C$ 250Air Canada

Find Deal

Mon, 20 Apr - Fri, 24 Apr

12:55 a.m. - 10:08 a.m.YYC-ORD

8h 13m1 stop

8:40 a.m. - 4:14 p.m.ORD-YYC

8h 34m1 stop

C$ 264Air Canada

Find Deal

Mon, 13 Apr - Thu, 16 Apr

6:00 a.m. - 9:13 p.m.YYC-ORD

14h 13m1 stop

8:46 a.m. - 11:37 a.m.ORD-YYC

3h 51mdirect

C$ 271United Airlines

Find Deal

Tue, 14 Apr - Thu, 16 Apr

1:27 p.m. - 11:57 p.m.YYC-ORD

9h 30m1 stop

8:46 a.m. - 11:37 a.m.ORD-YYC

3h 51mdirect

C$ 272United Airlines

Find Deal

Tue, 14 Apr - Thu, 16 Apr

5:45 a.m. - 3:10 p.m.YYC-ORD

8h 25m1 stop

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

3h 55mdirect

C$ 279Multiple Airlines

Find Deal

Mon, 20 Apr - Fri, 24 Apr

1:10 p.m. - 11:06 a.m.YYC-ORD

20h 56m2 stops

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

3h 55mdirect

C$ 296Multiple Airlines

Find Deal

Mon, 26 Jan - Fri, 30 Jan

7:40 a.m. - 6:32 p.m.YYC-MDW

9h 52m2 stops

1:49 p.m. - 8:54 p.m.MDW-YYC

8h 05m1 stop

C$ 312Delta

Find Deal

Wed, 14 Jan - Sun, 18 Jan

6:35 a.m. - 6:06 p.m.YYC-MDW

10h 31m2 stops

1:50 p.m. - 8:57 p.m.MDW-YYC

8h 07m1 stop

C$ 343Delta

Find Deal

Sat, 6 Dec - Tue, 16 Dec

United Airlines flights from Calgary to Chicago

Our best United Airlines deals on Calgary to Chicago flight tickets

United Airlines

14 Apr

YYC6:00 a.m.Calgary

14h 13m

1 stop

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

16 Apr

ORD8:46 a.m.Chicago O'Hare Intl

3h 51m

YYC11:37 a.m.Calgary

C$ 271

Find similar

United Airlines

14 Apr

YYC1:27 p.m.Calgary

9h 30m

1 stop

ORD11:57 p.m.Chicago O'Hare Intl

16 Apr

ORD8:46 a.m.Chicago O'Hare Intl

3h 51m

YYC11:37 a.m.Calgary

C$ 272

Find similar

United Airlines

21 Jan

YYC12:37 p.m.Calgary

3h 31m

ORD5:08 p.m.Chicago O'Hare Intl

25 Jan

ORD5:40 a.m.Chicago O'Hare Intl

8h 28m

1 stop

YYC1:08 p.m.Calgary

C$ 305

Find similar

Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets

Air Canada

20 Apr

YYC11:40 p.m.Calgary

8h 30m

1 stop

ORD9:10 a.m.Chicago O'Hare Intl

24 Apr

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

8h 34m

1 stop

YYC4:14 p.m.Calgary

C$ 250

Find similar

Air Canada

13 Apr

YYC12:55 a.m.Calgary

8h 13m

1 stop

ORD10:08 a.m.Chicago O'Hare Intl

16 Apr

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

8h 34m

1 stop

YYC4:14 p.m.Calgary

C$ 264

Find similar

Air Canada

8 Jan

YYC5:35 a.m.Calgary

8h 35m

1 stop

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

15 Jan

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

9h 54m

1 stop

YYC6:54 p.m.Calgary

C$ 302

Find similar

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 26/1

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

Nonstop3h 35m

Chicago O'Hare Intl

Fri 30/1

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

Nonstop3h 55m

C$ 206

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 20/4

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

Nonstop3h 35m

Chicago O'Hare Intl

Fri 24/4

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

Nonstop3h 55m

C$ 238

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 20/4

11:40 p.m.-9:10 a.m.

1 stop8h 30m

Chicago O'Hare Intl

Fri 24/4

8:40 a.m.-4:14 p.m.

1 stop8h 34m

C$ 250

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 13/4

12:55 a.m.-10:08 a.m.

1 stop8h 13m

Chicago O'Hare Intl

Thu 16/4

8:40 a.m.-4:14 p.m.

1 stop8h 34m

C$ 264

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 14/4

6:00 a.m.-9:13 p.m.

1 stop14h 13m

Chicago O'Hare Intl

Thu 16/4

8:46 a.m.-11:37 a.m.

Nonstop3h 51m

C$ 271

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 14/4

1:27 p.m.-11:57 p.m.

1 stop9h 30m

Chicago O'Hare Intl

Thu 16/4

8:46 a.m.-11:37 a.m.

Nonstop3h 51m

C$ 272

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 20/4

5:45 a.m.-3:10 p.m.

1 stop8h 25m

Chicago O'Hare Intl

Fri 24/4

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

Nonstop3h 55m

C$ 279

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 26/1

1:10 p.m.-11:06 a.m.

2 stops20h 56m

Chicago O'Hare Intl

Fri 30/1

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

Nonstop3h 55m

C$ 296

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 14/1

7:40 a.m.-6:32 p.m.

2 stops9h 52m

Chicago Midway

Sun 18/1

1:49 p.m.-8:54 p.m.

1 stop8h 05m

C$ 312

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 6/12

6:35 a.m.-6:06 p.m.

2 stops10h 31m

Chicago Midway

Tue 16/12

1:50 p.m.-8:57 p.m.

1 stop8h 07m

C$ 343

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$ 282.

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$ 664. 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$ 1,004. 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$ 372. 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$ 1,561 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$ 359 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$ 227 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$ 192
Fastest flight time	3h 27m
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$ 192. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is C$ 587.

The fastest flight from Calgary to Chicago takes 3h 27m

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 31m, 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 (24.76% of total bookings). The next most popular plane models are Airbus A319 (17.39%), Boeing 737-800 Passenger/BBJ2 (winglets) (14.23%), and Boeing 737 MAX 8 (14.12%).
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 10,476 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 180	Free Cancellation	Rating 7.2 3,173 reviews	Search WestJet flights
Delta	PriceFrom C$ 188	Free Cancellation	Rating 7.9 7,999 reviews	Search Delta flights
American Airlines	PriceFrom C$ 189	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 256	Free Cancellation	Rating 7.4 9,046 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$ 352, but momondo users have found Delta deals from Calgary to Chicago from as low as C$ 188 round-trip. Delta has been scored 7.9/10 in 7,998 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$ 256, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 525 round-trip. United Airlines operates 6 flights out of Calgary into Chicago in an average week, so prices vary by time and availability. 9,044 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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Thu 25/12

Thu 1/1

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Cheap flights from Calgary to Chicago from C$ 124

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 26/1. 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

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United Airlines flights from Calgary to Chicago

Our best United 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$ 282.

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?

WestJet, United Airlines, and Delta 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$ 242.

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 3 flights per day flying from Calgary to Chicago. The most common time of day flights depart is 12:00p.m., with 92% of flights taking off in the afternoon.

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

26 flights are operational weekly from Calgary to Chicago as of November 2025. The most popular departure day for this route is Mon, with 23% 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.