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

Alaska Airlines, United 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 39% of people opting to fly with this airline when traveling 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.

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

59 flights are operational weekly from Calgary to Chicago as of September 2026. The most popular departure day for this route is Mon, with 24% of flights per week taking off on this day.

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

8 flights are operational daily from Calgary to Chicago as of September 2026. The most popular departure time for this route is 12:00PM, with 65% 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 September 2026, 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 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.

$158 Cheap Flights from Calgary to Chicago in 2026/27

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Find the cheapest flights from Calgary to Chicago

Round-trip

One-way

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Cheap round-trip flights

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1:37 pm - 4:10 pmYYC Calgary-ORD Chicago O'Hare Intl

2h 33mnonstop

8:40 am - 1:35 pmORD Chicago O'Hare Intl-YYC Calgary

4h 55mnonstop

$259United Airlines

Fri, Dec 4 - Wed, Dec 9

1:37 pm - 4:10 pmYYC Calgary-ORD Chicago O'Hare Intl

2h 33mnonstop

8:40 am - 1:35 pmORD Chicago O'Hare Intl-YYC Calgary

4h 55mnonstop

$259United Airlines

Thu, Dec 3 - Wed, Dec 9

9:07 am - 12:10 pmYYC Calgary-ORD Chicago O'Hare Intl

27h 03m2 stops Seattle/Tacoma Intl Portland

6:00 am - 10:37 pmORD Chicago O'Hare Intl-YYC Calgary

16h 37m1 stop Seattle/Tacoma Intl

$263Alaska Airlines

Fri, Dec 4 - Wed, Dec 9

12:00 pm - 4:40 pmYYC Calgary-ORD Chicago O'Hare Intl

3h 40mnonstop

5:30 pm - 8:25 pmORD Chicago O'Hare Intl-YYC Calgary

3h 55mnonstop

$277WestJet

Mon, Oct 19 - Fri, Oct 23

12:30 pm - 5:05 pmYYC Calgary-ORD Chicago O'Hare Intl

3h 35mnonstop

8:40 am - 11:35 amORD Chicago O'Hare Intl-YYC Calgary

3h 55mnonstop

$278Lufthansa

Thu, Oct 22 - Wed, Oct 28

7:25 am - 5:26 pmYYC Calgary-ORD Chicago O'Hare Intl

10h 01m2 stops Salt Lake City Detroit Metropolitan Wayne County

2:04 pm - 1:21 amORD Chicago O'Hare Intl-YYC Calgary

11h 17m1 stop Salt Lake City

$288Delta

Thu, Dec 3 - Thu, Dec 10

2:52 pm - 5:39 pmYYC Calgary-ORD Chicago O'Hare Intl

2h 47mnonstop

9:42 am - 2:46 pmORD Chicago O'Hare Intl-YYC Calgary

5h 04mnonstop

$292American Airlines

Thu, Jan 28 - Mon, Feb 1

1:51 pm - 6:36 pmYYC Calgary-ORD Chicago O'Hare Intl

3h 45mnonstop

10:00 am - 12:51 pmORD Chicago O'Hare Intl-YYC Calgary

3h 51mnonstop

$295American Airlines

Thu, Oct 22 - Thu, Oct 29

1:43 pm - 8:56 pmYYC Calgary-ORD Chicago O'Hare Intl

7h 13m1 stop Salt Lake City

12:34 pm - 1:21 amORD Chicago O'Hare Intl-YYC Calgary

12h 47m2 stops Minneapolis St Paul Salt Lake City

$295Delta

Wed, Dec 2 - Tue, Dec 8

7:25 am - 5:05 pmYYC Calgary-ORD Chicago O'Hare Intl

9h 40m1 stop Salt Lake City

12:38 pm - 10:58 pmORD Chicago O'Hare Intl-YYC Calgary

10h 20m1 stop Minneapolis St Paul

$335WestJet

Fri, Nov 20 - Tue, Nov 24

Cheap last minute flights

Enter your travel dates to find the best prices.

1:51 pm - 6:36 pmYYC Calgary-ORD Chicago O'Hare Intl

3h 45mnonstop

5:00 am - 11:59 amORD Chicago O'Hare Intl-YYC Calgary

7h 59m1 stop Dallas/Fort Worth

$323American Airlines

Thu, Oct 1 - Mon, Oct 5

6:00 am - 11:59 pmYYC Calgary-ORD Chicago O'Hare Intl

16h 59m1 stop Denver Intl

4:20 pm - 9:48 pmORD Chicago O'Hare Intl-YYC Calgary

6h 28m1 stop Denver Intl

$323United Airlines

Sun, Oct 4 - Mon, Oct 5

2:15 pm - 9:33 pmYYC Calgary-ORD Chicago O'Hare Intl

6h 18m1 stop Minneapolis St Paul

2:05 pm - 11:06 pmORD Chicago O'Hare Intl-YYC Calgary

10h 01m1 stop Salt Lake City

$338Delta

Thu, Oct 1 - Mon, Oct 5

1:51 pm - 6:36 pmYYC Calgary-ORD Chicago O'Hare Intl

3h 45mnonstop

8:30 pm - 11:29 pmORD Chicago O'Hare Intl-YYC Calgary

3h 59mnonstop

$351American Airlines

Wed, Sep 30 - Fri, Oct 2

12:30 pm - 5:05 pmYYC Calgary-ORD Chicago O'Hare Intl

3h 35mnonstop

6:00 am - 9:48 pmORD Chicago O'Hare Intl-YYC Calgary

16h 48m1 stop Denver Intl

$354United Airlines

Wed, Sep 30 - Fri, Oct 2

6:35 am - 1:20 pmYYC Calgary-MDW Chicago Midway

5h 45m1 stop Minneapolis St Paul

12:27 pm - 8:40 pmMDW Chicago Midway-YYC Calgary

9h 13m1 stop Minneapolis St Paul

$359Delta

Wed, Sep 30 - Wed, Oct 7

9:20 am - 4:35 pmYYC Calgary-ORD Chicago O'Hare Intl

6h 15m1 stop Winnipeg

8:40 am - 11:28 amORD Chicago O'Hare Intl-YYC Calgary

3h 48mnonstop

$427Air Canada

Wed, Sep 30 - Tue, Oct 6

2:15 pm - 9:33 pmYYC Calgary-ORD Chicago O'Hare Intl

6h 18m1 stop Minneapolis St Paul

12:30 pm - 8:40 pmORD Chicago O'Hare Intl-YYC Calgary

9h 10m1 stop Minneapolis St Paul

$456WestJet

Thu, Oct 1 - Tue, Oct 6

6:30 am - 2:55 pmYYC Calgary-ORD Chicago O'Hare Intl

7h 25m1 stop Toronto Pearson Intl

2:15 pm - 9:05 pmORD Chicago O'Hare Intl-YYC Calgary

7h 50m1 stop Toronto Pearson Intl

$505Air Canada

Fri, Oct 2 - Mon, Oct 5

6:35 am - 4:59 pmYYC Calgary-ORD Chicago O'Hare Intl

9h 24m1 stop Minneapolis St Paul

5:30 pm - 8:25 pmORD Chicago O'Hare Intl-YYC Calgary

3h 55mnonstop

$639WestJet

Mon, Oct 5 - Mon, Oct 12

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United Airlines flights from Calgary to Chicago

Our best United Airlines deals on Calgary to Chicago flight tickets

United Airlines

Dec 3

YYC1:37 pmCalgary

2h 33m

ORD4:10 pmChicago O'Hare Intl

Dec 9

ORD8:40 amChicago O'Hare Intl

4h 55m

YYC1:35 pmCalgary

$259

United Airlines

Dec 3

YYC1:37 pmCalgary

2h 33m

ORD4:10 pmChicago O'Hare Intl

Dec 9

ORD12:29 pmChicago O'Hare Intl

11h 24m

1 stop

YYC11:53 pmCalgary

$269

United Airlines

Dec 4

YYC3:06 pmCalgary

5h 28m

1 stop

ORD8:34 pmChicago O'Hare Intl

Dec 9

ORD8:40 amChicago O'Hare Intl

4h 55m

YYC1:35 pmCalgary

$274

WestJet flights from Calgary to Chicago

Our best WestJet deals on Calgary to Chicago flight tickets

WestJet

Oct 19

YYC12:00 pmCalgary

3h 40m

ORD4:40 pmChicago O'Hare Intl

Oct 23

ORD5:30 pmChicago O'Hare Intl

3h 55m

YYC8:25 pmCalgary

$277

WestJet

Oct 27

YYC7:52 amCalgary

8h 02m

1 stop

MDW4:54 pmChicago Midway

Nov 3

MDW12:34 pmChicago Midway

10h 13m

1 stop

YYC10:47 pmCalgary

$367

WestJet

Oct 24

YYC7:52 amCalgary

8h 02m

1 stop

MDW4:54 pmChicago Midway

Oct 31

MDW12:34 pmChicago Midway

9h 13m

1 stop

YYC8:47 pmCalgary

$420

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 12/4

1:37 pm-4:10 pm

Nonstop2h 33m

Chicago O'Hare Intl

Wed 12/9

8:40 am-1:35 pm

Nonstop4h 55m

$259

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 12/3

1:37 pm-4:10 pm

Nonstop2h 33m

Chicago O'Hare Intl

Wed 12/9

8:40 am-1:35 pm

Nonstop4h 55m

$259

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 12/4

9:07 am-12:10 pm

2 stops27h 03m

Chicago O'Hare Intl

Wed 12/9

6:00 am-10:37 pm

1 stop16h 37m

$263

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Mon 10/19

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Fri 10/23

5:30 pm-8:25 pm

Nonstop3h 55m

$277

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 10/22

12:30 pm-5:05 pm

Nonstop3h 35m

Chicago O'Hare Intl

Wed 10/28

8:40 am-11:35 am

Nonstop3h 55m

$278

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 12/3

7:25 am-5:26 pm

2 stops10h 01m

Chicago O'Hare Intl

Thu 12/10

2:04 pm-1:21 am

1 stop11h 17m

$288

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 1/28

2:52 pm-5:39 pm

Nonstop2h 47m

Chicago O'Hare Intl

Mon 2/1

9:42 am-2:46 pm

Nonstop5h 04m

$292

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 10/22

1:51 pm-6:36 pm

Nonstop3h 45m

Chicago O'Hare Intl

Thu 10/29

10:00 am-12:51 pm

Nonstop3h 51m

$295

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Wed 12/2

1:43 pm-8:56 pm

1 stop7h 13m

Chicago O'Hare Intl

Tue 12/8

12:34 pm-1:21 am

2 stops12h 47m

$295

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 11/20

7:25 am-5:05 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 11/24

12:38 pm-10:58 pm

1 stop10h 20m

$335

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?

Prices are currently typical for flights on this route.

Typical prices usually range from $220 to $365.
The lowest price recently found on this route was $259.

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $253. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Calgary to Chicago during May average around $260.

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 $405. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago for around $620.

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 $388. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $806.

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 $316 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 $224 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 September 2026, prices for Calgary to Chicago flights are approximately 40% 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	$158
Fastest flight time	2h 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 $158. The best round-trip flight deal from Calgary to Chicago found on momondo in the last 72 hours is $259.

The fastest flight from Calgary to Chicago takes 2h 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 2h 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 September 2026, 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 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 48.29% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 12.86%, Boeing 737-700 Passenger/BBJ1 (winglets) at 10.92%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 10.38%.
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 59% of the total bookings. Other popular airlines include American Airlines with 21% and United Airlines with 20%.

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
United Airlines	PriceFrom $135	Free Cancellation	Rating 7.4 10,251 reviews	Search United Airlines flights
Air Canada	PriceFrom $149	Free Cancellation	Rating 7.1 11,703 reviews	Search Air Canada flights
WestJet	PriceFrom $163	Free Cancellation	Rating 7.2 3,449 reviews	Search WestJet flights
American Airlines	PriceFrom $244	Free Cancellation	Rating 7.0 12,096 reviews	Search American Airlines flights
Delta	PriceFrom $253	Free Cancellation	Rating 7.8 8,610 reviews	Search Delta flights

Delta Flights From Calgary to Chicago
Delta operates around 2 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been $371, but momondo users have found Delta deals from Calgary to Chicago from as low as $253 round-trip. Delta has been scored 7.8/10 in 8,610 reviews.
United Airlines Flights From Calgary to Chicago
Another popular option for Calgary to Chicago flights is United Airlines (7.4/10, 10,251 ratings). United Airlines flies from Calgary to Chicago around 6 times per week, with deals starting from $135 round-trip and rising to an average price of around $355.

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

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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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 $158

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 10/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

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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

WestJet flights from Calgary to Chicago

Our best WestJet 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 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.

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

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