$85 Cheap Flights from Chicago (ORD) to Calgary (YYC)

View $85 flight on Mon, May 25, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Calgary International Airport (YYC)

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Cheap Flights from Chicago to Calgary (ORD-YYC)

Prices were available within the past 7 days and start at $85 for one-way flights and $219 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Wed, May 27 - Sat, May 30
ORD
Chicago
YYC
Calgary
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select WestJet flight, departing Wed, May 27 from Chicago to Calgary, returning Sat, May 30, priced at $219 found 1 hour ago
Delta
Sun, May 17 - Sun, May 24
ORD
Chicago
YYC
Calgary
$219 Roundtrip, just found
$219
Roundtrip
just found
Select Delta flight, departing Sun, May 17 from Chicago to Calgary, returning Sun, May 24, priced at $219 just found
WestJet
Sun, May 24 - Wed, May 27
ORD
Chicago
YYC
Calgary
$220 Roundtrip, just found
$220
Roundtrip
just found
Select WestJet flight, departing Sun, May 24 from Chicago to Calgary, returning Wed, May 27, priced at $220 just found
WestJet
Wed, May 27 - Fri, May 29
ORD
Chicago
YYC
Calgary
$221 Roundtrip, just found
$221
Roundtrip
just found
Select WestJet flight, departing Wed, May 27 from Chicago to Calgary, returning Fri, May 29, priced at $221 just found
WestJet
Sat, May 23 - Tue, May 26
ORD
Chicago
YYC
Calgary
$222 Roundtrip, just found
$222
Roundtrip
just found
Select WestJet flight, departing Sat, May 23 from Chicago to Calgary, returning Tue, May 26, priced at $222 just found
Delta
Sun, May 17 - Thu, May 21
ORD
Chicago
YYC
Calgary
$232 Roundtrip, found 13 hours ago
$232
Roundtrip
found 13 hours ago
Select Delta flight, departing Sun, May 17 from Chicago to Calgary, returning Thu, May 21, priced at $232 found 13 hours ago
WestJet
Tue, May 26 - Tue, Jun 9
ORD
Chicago
YYC
Calgary
$235 Roundtrip, found 1 day ago
$235
Roundtrip
found 1 day ago
Select WestJet flight, departing Tue, May 26 from Chicago to Calgary, returning Tue, Jun 9, priced at $235 found 1 day ago
Air Canada
Sat, Oct 17 - Wed, Oct 21
ORD
Chicago
YYC
Calgary
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Oct 17 from Chicago to Calgary, returning Wed, Oct 21, priced at $242 found 2 days ago
American Airlines
Tue, Sep 15 - Tue, Sep 22
ORD
Chicago
YYC
Calgary
$257 Roundtrip, just found
$257
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 15 from Chicago to Calgary, returning Tue, Sep 22, priced at $257 just found
United
Sat, Jun 6 - Wed, Jun 10
ORD
Chicago
YYC
Calgary
$265 Roundtrip, found 1 hour ago
$265
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Jun 6 from Chicago to Calgary, returning Wed, Jun 10, priced at $265 found 1 hour ago

Alternative airports near Calgary

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Calgary Intl. YYC. Cheapest and Closest option available. Average driving time to city center is 15 minutes. Flights from $314
YYC
Calgary Intl.
CheapestClosest
Average driving time to city center15 min
Flights from $314

Find the cheapest month to fly from Chicago (ORD) to Calgary (YYC)

May is typically the cheapest month to fly

From $211 - $476 per traveler.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) cost?
You can find cheap one-way flights and cheap return flights from $219 Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) with Expedia. One-way flights typically cost between $134 and $1192, and return flights often range between $319 and $1798. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
October is typically the cheapest month to fly from Chicago (ORD) to Calgary (YYC), with average return fares around $319. This is about 23% lower than the average price throughout the year, as travel demand decreases after the summer. Other affordable months to consider are January and May.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
Choose from 3 airlines operating direct flights from ORD to YYC:

  • American Airlines operates around 11 direct flights from ORD to YYC every week
  • United operates around 9 direct flights from ORD to YYC every week
  • WestJet operates around 7 direct flights from ORD to YYC every week

What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
American Airlines is one of the cheapest airlines offering nonstop flights from O'Hare Intl. (ORD) to Calgary Intl. (YYC), with round-trip tickets starting from around $291. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
The best airline to fly with from Chicago, IL (ORD) to Calgary, AB (YYC) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, American Airlines typically offers the lowest fares. United offers the most daily flights from ORD to YYC, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
For flights from Chicago to Calgary, October and January are your best bets. You can expect return flights to be around $319 in these months. October is great for enjoying the fall scenery, while January offers lower prices as travel demand decreases after the holiday season.*Prices based on flights available on Expedia in the last year.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
You can find approximately 4 nonstop flights per day from O'Hare Intl. (ORD) to Calgary Intl. (YYC). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
The earliest flight from Chicago O'Hare International Airport (ORD) to Calgary International Airport (YYC) typically departs at around 12:55 AM. This seasonal service is operated by American Airlines, allowing you to start your journey early and make the most of your time in Calgary. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
The most popular departure times for flights from O'Hare International Airport (ORD) in Chicago to Calgary International Airport (YYC) are in the early morning, from 6am to 9am. This accounts for around 28% of total traffic. Many major carriers, including United Airlines and Air Canada, offer flights during this window. This timing is favored because it allows travelers to arrive in Calgary with plenty of time to explore the city.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
A nonstop flight from ORD to YYC typically takes around 3 hours 50 minutes, covering approximately 1,382 miles. Connecting flights on this route usually add 4 hours 30 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
Business class seats are offered on the ORD to YYC route. Airlines that offer business class service on this route include:

  • Air Canada
  • United Airlines
  • American Airlines

First class cabins are available on:

  • Delta Air Lines
  • United Airlines
  • American Airlines
  • WestJet

How much is a business class flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
A direct, return business class ticket from Chicago (ORD) to Calgary (YYC) typically costs between $1,283 - $1,852. A non-stop, one-way business class flight is usually around $497 - $700. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Calgary from O'Hare Intl. (ORD)?
From O'Hare Intl. (ORD), you can fly into Calgary Intl. (YYC) to reach Calgary. Some flights may connect through major hubs like Portland Intl. (PDX), Pearson Intl. (YYZ), Seattle - Tacoma Intl. (SEA) before reaching Calgary. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) Calgary Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Calgary Intl.
Airlines serving
Air Canada, Alaska Airlines, American Airlines, Delta, Porter Airlines, United, WestJet
Roundtrip price
$218
Distance
1381 mi
Average flight time
2 hours 56 mins

Book with confidence

Chicago to Calgary Flights

The cheapest times to fly from Chicago to Calgary

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Calgary are during the month of May. You can find some of the cheapest flights from Chicago to Calgary with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Calgary

Sunday is one of the best days to book for cheap flights from Chicago to Calgary: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Calgary

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Calgary in 2026. You can also book with separate airlines for your outbound and return journeys, from $85 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Calgary flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Calgary airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Calgary Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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