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

92 flights are operational weekly from Calgary to Chicago as of July 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

What airlines fly to Chicago?

WestJet, United Airlines and American 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 44% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

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

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

13 flights are operational daily from Calgary to Chicago as of July 2026. The most popular departure time for this route is 12:00PM, with 58% of flights per day 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 were last updated today.

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

As of July 2026, there are 4 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 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 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.

$100 Cheap Flights from Calgary to Chicago in 2026

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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.

12:00 pm - 4:40 pm

YYC

ORD

3h 40mnonstop

5:30 pm - 8:25 pm

ORD

YYC

3h 55mnonstop

$229WestJet

Sat, Aug 29 - Sat, Sep 5

12:37 pm - 5:10 pm

YYC

ORD

3h 33mnonstop

8:40 am - 11:35 am

ORD

YYC

3h 55mnonstop

$235United Airlines

Mon, Oct 26 - Wed, Oct 28

12:37 pm - 5:10 pm

YYC

ORD

3h 33mnonstop

9:47 pm - 2:56 pm

ORD

YYC

17h 09m

1 stop

$245United Airlines

Fri, Oct 30 - Mon, Nov 2

12:37 pm - 5:10 pm

YYC

ORD

3h 33mnonstop

9:47 pm - 2:56 pm

ORD

YYC

17h 09m

1 stop

$246United Airlines

Fri, Oct 30 - Mon, Nov 2

12:00 pm - 4:40 pm

YYC

ORD

3h 40mnonstop

5:30 pm - 8:25 pm

ORD

YYC

3h 55mnonstop

$248WestJet

Sat, Aug 29 - Mon, Aug 31

12:00 pm - 4:40 pm

YYC

ORD

3h 40mnonstop

5:30 pm - 8:25 pm

ORD

YYC

3h 55mnonstop

$251WestJet

Fri, Oct 2 - Tue, Oct 6

12:00 pm - 4:40 pm

YYC

ORD

3h 40mnonstop

5:30 pm - 8:25 pm

ORD

YYC

3h 55mnonstop

$253WestJet

Fri, Sep 11 - Mon, Sep 14

2:15 pm - 9:47 pm

YYC

ORD

6h 32m

1 stop

2:00 pm - 11:04 pm

ORD

YYC

10h 04m

1 stop

$262Delta

Sat, Aug 22 - Mon, Aug 31

6:00 am - 3:38 pm

YYC

ORD

8h 38m

1 stop

10:15 am - 6:54 pm

ORD

YYC

8h 39m

1 stop

$263Air Canada

Fri, Oct 30 - Mon, Nov 2

7:45 am - 9:10 pm

YYC

MDW

13h 25m

2 stops

9:30 am - 9:54 pm

MDW

YYC

12h 24m

2 stops

$267Delta

Mon, Nov 23 - Thu, Nov 26

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Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets

Air Canada

Oct 30

YYC6:00 amCalgary

8h 38m

1 stop

ORD3:38 pmChicago O'Hare Intl

Nov 2

ORD10:15 amChicago O'Hare Intl

8h 39m

1 stop

YYC6:54 pmCalgary

$263

Air Canada

Aug 18

YYC6:30 amCalgary

7h 25m

1 stop

ORD2:55 pmChicago O'Hare Intl

Aug 25

ORD8:40 amChicago O'Hare Intl

8h 28m

1 stop

YYC4:08 pmCalgary

$273

Air Canada

Nov 11

YYC7:00 amCalgary

7h 38m

1 stop

ORD2:38 pmChicago O'Hare Intl

Nov 21

ORD4:30 pmChicago O'Hare Intl

8h 54m

1 stop

YYC1:24 amCalgary

$279

United Airlines flights from Calgary to Chicago

Our best United Airlines deals on Calgary to Chicago flight tickets

United Airlines

Oct 26

YYC12:37 pmCalgary

3h 33m

ORD5:10 pmChicago O'Hare Intl

Oct 28

ORD8:40 amChicago O'Hare Intl

3h 55m

YYC11:35 amCalgary

$235

United Airlines

Oct 30

YYC12:37 pmCalgary

3h 33m

ORD5:10 pmChicago O'Hare Intl

Nov 2

ORD9:47 pmChicago O'Hare Intl

17h 09m

1 stop

YYC2:56 pmCalgary

$245

United Airlines

Oct 30

YYC12:37 pmCalgary

3h 33m

ORD5:10 pmChicago O'Hare Intl

Nov 2

ORD9:47 pmChicago O'Hare Intl

17h 09m

1 stop

YYC2:56 pmCalgary

$246

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 8/29

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sat 9/5

5:30 pm-8:25 pm

Nonstop3h 55m

$229

Quickest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 10/26

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Wed 10/28

8:40 am-11:35 am

Nonstop3h 55m

$235

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/30

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Mon 11/2

9:47 pm-2:56 pm

1 stop17h 09m

$245

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/30

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Mon 11/2

9:47 pm-2:56 pm

1 stop17h 09m

$246

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 8/29

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Mon 8/31

5:30 pm-8:25 pm

Nonstop3h 55m

$248

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/2

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 10/6

5:30 pm-8:25 pm

Nonstop3h 55m

$251

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 9/11

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Mon 9/14

5:30 pm-8:25 pm

Nonstop3h 55m

$253

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 8/22

2:15 pm-9:47 pm

1 stop6h 32m

Chicago O'Hare Intl

Mon 8/31

2:00 pm-11:04 pm

1 stop10h 04m

$262

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/30

6:00 am-3:38 pm

1 stop8h 38m

Chicago O'Hare Intl

Mon 11/2

10:15 am-6:54 pm

1 stop8h 39m

$263

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 11/23

7:45 am-9:10 pm

2 stops13h 25m

Chicago Midway

Thu 11/26

9:30 am-9:54 pm

2 stops12h 24m

$267

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

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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 November is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $231. If you’re not able to fly to Chicago in November, then January is your next best option. Flight prices from Calgary to Chicago during January average around $239.

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 $314. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago for around $539.

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Calgary to Chicago during this time can be as low as $369. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $876.

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 from Calgary 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 $292 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 $217 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 15% 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 July 2026, prices for Calgary to Chicago flights are approximately 7% 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	$230
Fastest flight time	3h 20m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Calgary in the past 72 hours is $230. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is $373.

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

Direct flights go from Calgary to Chicago every day.

There are 3 airports in Chicago. From Calgary there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Calgary to Chicago

How far is Calgary to Chicago by plane?
Chicago is 1397.6 mi away from Calgary. In terms of flight time, this usually takes a little over 3h 20m.
When did momondo last update prices for flights from Calgary Airport to Chicago?
Prices for flights from Calgary Airport to Chicago were last updated today.
How many operators does momondo search for flights from Calgary Airport to Chicago?
As of July 2026, there are 4 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 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 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?
momondo data reveals that the most frequently booked plane model on the route from Calgary to Chicago is Boeing 737-800, representing 50.26% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 13.26%, Boeing 737 MAX 8 at 8.25%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 7.44%.
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 61% of the total bookings. Other popular airlines include American Airlines with 23% and United Airlines with 16%.

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 $135	Free Cancellation	Rating 7.1 11,360 reviews	Search Air Canada flights
United Airlines	PriceFrom $135	Free Cancellation	Rating 7.4 10,014 reviews	Search United Airlines flights
WestJet	PriceFrom $137	Free Cancellation	Rating 7.2 3,411 reviews	Search WestJet flights
American Airlines	PriceFrom $208	Free Cancellation	Rating 7.1 11,825 reviews	Search American Airlines flights

United Airlines Flights From Calgary to Chicago
United Airlines operates around 10 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been $398, but momondo users have found United Airlines deals from Calgary to Chicago from as low as $135 round-trip. United Airlines has been scored 7.4/10 in 10,014 reviews.
WestJet Flights From Calgary to Chicago
Another popular option for Calgary to Chicago flights is WestJet (7.2/10, 3,411 ratings). WestJet flies from Calgary to Chicago around 6 times per week, with deals starting from $137 round-trip and rising to an average price of around $261.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Saint Joseph

Lansing

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

Porter

Griffith

Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Calgary to Chicago for you.

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

Yes. momondo allows you to filter the results for Calgary to Chicago flights to just show those with flexible booking policies.

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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Calgary and alert you when they change.

An easier way to manage your Chicago trip

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Cheap flights from Calgary to Chicago from $174

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 9/17. 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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Air Canada flights from Calgary to Chicago

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United Airlines flights from Calgary to Chicago

Our best United Airlines deals on Calgary to Chicago flight tickets

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How to get the cheapest flight ticket from Calgary to Chicago

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

What is the cheapest month to fly to Chicago?

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?

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

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

Can stopping save me money on Calgary to Chicago flights?

How have Calgary to Chicago flight prices changed over time?

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

What airlines fly to Chicago?

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

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

When to book flights from Calgary to Chicago

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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

Traveling to a place near Chicago?

Why use momondo?

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.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

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

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