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

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

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 43% 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.

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

21 flights are operational weekly from Calgary to Chicago as of February 2026. The most popular departure day for this route is Mon, with 43% of flights per week taking off on this day.

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

3 flights are operational daily from Calgary to Chicago as of February 2026. The most popular departure time for this route is 12:00PM, with 90% 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 February 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.

$98 Cheap Flights from Calgary to Chicago in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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 am - 1:35 pm

YYC

ORD

3h 35mnonstop

2:20 pm - 5:15 pm

ORD

YYC

3h 55mnonstop

$181WestJet

Fri, Apr 3 - Fri, Apr 10

12:00 pm - 4:40 pm

YYC

ORD

3h 40mnonstop

5:30 pm - 8:25 pm

ORD

YYC

3h 55mnonstop

$185WestJet

Sat, May 30 - Tue, Jun 2

12:00 pm - 4:40 pm

YYC

ORD

3h 40mnonstop

5:30 pm - 8:25 pm

ORD

YYC

3h 55mnonstop

$186WestJet

Mon, May 11 - Sun, May 17

12:00 pm - 4:40 pm

YYC

ORD

3h 40mnonstop

5:30 pm - 8:25 pm

ORD

YYC

3h 55mnonstop

$187WestJet

Sun, May 10 - Wed, May 20

6:00 am - 11:28 pm

YYC

ORD

16h 28m

1 stop

8:42 am - 11:32 am

ORD

YYC

3h 50mnonstop

$206United Airlines

Thu, Apr 16 - Tue, Apr 21

5:45 am - 3:15 pm

YYC

ORD

8h 30m

1 stop

9:55 am - 6:43 pm

ORD

YYC

9h 48m

1 stop

$213Air Canada

Wed, Apr 29 - Sat, May 2

6:30 am - 1:25 pm

YYC

MDW

5h 55m

1 stop

9:35 am - 8:45 pm

MDW

YYC

12h 10m

2 stops

$262Delta

Tue, Mar 10 - Tue, Mar 17

8:55 am - 7:47 pm

YYC

MDW

9h 52m

1 stop

6:05 am - 11:43 am

MDW

YYC

30h 38m

1 stop

$267Multiple Airlines

Fri, Mar 6 - Mon, Mar 9

8:55 am - 10:29 pm

YYC

MDW

12h 34m

1 stop

6:00 am - 11:43 am

MDW

YYC

30h 43m

1 stop

$268Multiple Airlines

Thu, Feb 26 - Mon, Mar 2

7:40 am - 10:28 pm

YYC

MDW

13h 48m

2 stops

6:30 am - 10:57 pm

MDW

YYC

17h 27m

2 stops

$287Delta

Mon, May 4 - Thu, May 7

WestJet flights from Calgary to Chicago

Our best WestJet deals on Calgary to Chicago flight tickets

WestJet

Apr 3

YYC9:00 amCalgary

3h 35m

ORD1:35 pmChicago O'Hare Intl

Apr 10

ORD2:20 pmChicago O'Hare Intl

3h 55m

YYC5:15 pmCalgary

$181

WestJet

May 30

YYC12:00 pmCalgary

3h 40m

ORD4:40 pmChicago O'Hare Intl

Jun 2

ORD5:30 pmChicago O'Hare Intl

3h 55m

YYC8:25 pmCalgary

$185

WestJet

May 11

YYC12:00 pmCalgary

3h 40m

ORD4:40 pmChicago O'Hare Intl

May 17

ORD5:30 pmChicago O'Hare Intl

3h 55m

YYC8:25 pmCalgary

$186

Air Canada flights from Calgary to Chicago

Our best Air Canada deals on Calgary to Chicago flight tickets

Air Canada

Apr 29

YYC5:45 amCalgary

8h 30m

1 stop

ORD3:15 pmChicago O'Hare Intl

May 2

ORD9:55 amChicago O'Hare Intl

9h 48m

1 stop

YYC6:43 pmCalgary

$213

Air Canada

Mar 27

YYC5:35 amCalgary

8h 35m

1 stop

ORD3:10 pmChicago O'Hare Intl

Apr 3

ORD6:40 pmChicago O'Hare Intl

14h 48m

1 stop

YYC8:28 amCalgary

$231

Air Canada

Mar 31

YYC9:00 amCalgary

8h 53m

1 stop

ORD6:53 pmChicago O'Hare Intl

Apr 8

ORD10:43 amChicago O'Hare Intl

10h 15m

1 stop

YYC7:58 pmCalgary

$233

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 4/3

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Fri 4/10

2:20 pm-5:15 pm

Nonstop3h 55m

$181

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/30

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 6/2

5:30 pm-8:25 pm

Nonstop3h 55m

$185

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 5/11

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sun 5/17

5:30 pm-8:25 pm

Nonstop3h 55m

$186

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 5/10

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Wed 5/20

5:30 pm-8:25 pm

Nonstop3h 55m

$187

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 4/16

6:00 am-11:28 pm

1 stop16h 28m

Chicago O'Hare Intl

Tue 4/21

8:42 am-11:32 am

Nonstop3h 50m

$206

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 4/29

5:45 am-3:15 pm

1 stop8h 30m

Chicago O'Hare Intl

Sat 5/2

9:55 am-6:43 pm

1 stop9h 48m

$213

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 3/10

6:30 am-1:25 pm

1 stop5h 55m

Chicago Midway

Tue 3/17

9:35 am-8:45 pm

2 stops12h 10m

$262

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 3/6

8:55 am-7:47 pm

1 stop9h 52m

Chicago Midway

Mon 3/9

6:05 am-11:43 am

1 stop30h 38m

$267

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 2/26

8:55 am-10:29 pm

1 stop12h 34m

Chicago Midway

Mon 3/2

6:00 am-11:43 am

1 stop30h 43m

$268

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/4

7:40 am-10:28 pm

2 stops13h 48m

Chicago Midway

Thu 5/7

6:30 am-10:57 pm

2 stops17h 27m

$287

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

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 April is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $188. If you’re not able to fly to Chicago in April, then November is your next best option. Flight prices from Calgary to Chicago during November average around $189.

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 Sunday when prices can be found for as low as $181. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago for around $482.

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 $347. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $833.

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 $265 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 $205 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?

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

How have Calgary to Chicago flight prices changed over time?

As of February 2026, prices for Calgary to Chicago flights are approximately 26% 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	$185
Fastest flight time	3h 32m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Calgary in the past 72 hours is $185. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is $216.

The fastest flight from Calgary to Chicago takes 3h 32m

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

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 32m.
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 February 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 MAX 8, representing 24.47% of all bookings. The subsequent popular models are Boeing 737-700 at 23.62%, Boeing 737-700 Passenger/BBJ1 (winglets) at 16.42%, and Airbus A319 at 8.90%.
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 52% of the total bookings. Other popular airlines include American Airlines with 20%, United Airlines with 12%, and Air Canada with 9%.

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 $101	Free Cancellation	Rating 7.1 10,709 reviews	Search Air Canada flights
WestJet	PriceFrom $138	Free Cancellation	Rating 7.2 3,256 reviews	Search WestJet flights
United Airlines	PriceFrom $168	Free Cancellation	Rating 7.4 9,279 reviews	Search United Airlines flights
American Airlines	PriceFrom $185	Free Cancellation	Rating 7.2 11,271 reviews	Search American Airlines flights

United Airlines Flights From Calgary to Chicago
United Airlines operates around 3 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been $460, but momondo users have found United Airlines deals from Calgary to Chicago from as low as $168 round-trip. United Airlines has been scored 7.4/10 in 9,279 reviews.
WestJet Flights From Calgary to Chicago
Another popular option for Calgary to Chicago flights is WestJet (7.2/10, 3,256 ratings). WestJet flies from Calgary to Chicago around 1 time per week, with deals starting from $138 round-trip and rising to an average price of around $238.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

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

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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Fri 3/13

Fri 3/20

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Calgary

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Calgary to Chicago from $98

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 5/4. 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 and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

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

momondo Fare Finder

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

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 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

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

Best airlines flying from Calgary to Chicago

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

United Airlines Flights From Calgary to Chicago

WestJet Flights From Calgary to Chicago

Traveling 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.

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.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Calgary

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year