CA $135 Cheap Flights from Chicago (ORD) to Calgary (YYC)

View CA $135 flight on Sun, May 24, 2026Opens in a new window

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

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Cheap flights from Chicago (ORD) to Calgary (YYC)

Prices were available within the past 7 days and start at CA $135 for one-way flights and CA $321 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Sat, May 23 - Wed, May 27
ORD
Chicago
YYC
Calgary
CA $321 Roundtrip, found 1 hour ago
CA $321
Roundtrip
found 1 hour ago
Select WestJet flight, departing Sat, May 23 from Chicago to Calgary, returning Wed, May 27, priced at CA $321 found 1 hour ago
Delta
Sat, May 16 - Sun, May 24
ORD
Chicago
YYC
Calgary
CA $326 Roundtrip, found 4 days ago
CA $326
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, May 16 from Chicago to Calgary, returning Sun, May 24, priced at CA $326 found 4 days ago
Delta
Sat, May 16 - Mon, May 18
ORD
Chicago
YYC
Calgary
CA $327 Roundtrip, found 4 days ago
CA $327
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, May 16 from Chicago to Calgary, returning Mon, May 18, priced at CA $327 found 4 days ago
Delta
Tue, May 5 - Mon, May 11
ORD
Chicago
YYC
Calgary
CA $328 Roundtrip, found 5 days ago
CA $328
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, May 5 from Chicago to Calgary, returning Mon, May 11, priced at CA $328 found 5 days ago
WestJet
Sat, May 23 - Sat, May 30
ORD
Chicago
YYC
Calgary
CA $328 Roundtrip, found 2 days ago
CA $328
Roundtrip
found 2 days ago
Select WestJet flight, departing Sat, May 23 from Chicago to Calgary, returning Sat, May 30, priced at CA $328 found 2 days ago
Delta
Sun, May 24 - Thu, May 28
ORD
Chicago
YYC
Calgary
CA $333 Roundtrip, found 16 hours ago
CA $333
Roundtrip
found 16 hours ago
Select Delta flight, departing Sun, May 24 from Chicago to Calgary, returning Thu, May 28, priced at CA $333 found 16 hours ago
Delta
Sat, May 16 - Sun, May 24
ORD
Chicago
YYC
Calgary
CA $336 Roundtrip, found 4 days ago
CA $336
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, May 16 from Chicago to Calgary, returning Sun, May 24, priced at CA $336 found 4 days ago
United
Mon, May 25 - Tue, May 26
ORD
Chicago
YYC
Calgary
CA $337 Roundtrip, found 19 hours ago
CA $337
Roundtrip
found 19 hours ago
Select United flight, departing Mon, May 25 from Chicago to Calgary, returning Tue, May 26, priced at CA $337 found 19 hours ago
Air Canada
Tue, May 12 - Sun, May 17
ORD
Chicago
YYC
Calgary
CA $346 Roundtrip, found 6 days ago
CA $346
Roundtrip
found 6 days ago
Select Air Canada flight, departing Tue, May 12 from Chicago to Calgary, returning Sun, May 17, priced at CA $346 found 6 days ago
American Airlines
Mon, Jun 1 - Sat, Jun 6
ORD
Chicago
YYC
Calgary
CA $365 Roundtrip, found 1 day ago
CA $365
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jun 1 from Chicago to Calgary, returning Sat, Jun 6, priced at CA $365 found 1 day 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 centre is 15 minutes. Flights from CA $348
YYC
Calgary Intl.
CheapestClosest
Average driving time to city centre15 min
Flights from CA $348

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

May is typically the cheapest month to fly

From CA $294 - CA $664 per traveller.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) cost?
One-way flights typically cost between $373 and $2,614 and return flights often range between $1,131 and $4,462. 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 Anaa (AAA) to Toronto, ON (YYZ-Pearson Intl.) ticket fares go up or down.
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, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.), with average round-trip fares around 775 CAD. This is about 23% lower than the average price throughout the year. October often sees lower prices as the peak summer travel season has ended and before the winter holiday rush begins, leading to reduced demand. Other cheap months to fly from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) include January and May.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
Enter ORD to YYC and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
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-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) will differ from traveler to traveler. If you like to fly early, UA offers early morning flights. If price is the most important factor, AA typically offers the lowest fares. UA offers the most daily flights from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.), 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.)?
When looking for the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.), it's a balance between price and popularity. Based on booking data from the past year, you'll find the cheapest flights in October and January, with average prices around 775 CAD for a round-trip. However, the most popular months for travel are August and December, which means more flight options and potentially higher demand. If you're prioritizing savings, aim for October or January, but be aware that August and December offer more flexibility in flight times due to higher travel volumes.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
When flying from Chicago O'Hare International Airport (ORD) to Calgary International Airport (YYC), you'll find approximately 5 nonstop flights per day. For even more choice, look at flights that include layovers, as there are around 137 connecting flights daily. Some common connection points include Seattle - Tacoma Intl. (SEA), Minneapolis - St. Paul Intl. (MSP), and Pearson Intl. (YYZ).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) typically departs at approximately 12:55 AM local time, operated by American Airlines. This is a seasonal service active in January. An early departure like this can help maximize your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
You'll typically find the most flights from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) on a Wednesday, with around 70 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include United Airlines, Delta Air Lines, and American Airlines. Flight schedules are consistent throughout the week, so you'll have a good selection of flights no matter which day you choose.
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 Chicago O'Hare International Airport (ORD) to Calgary International Airport (YYC) are in the early morning, from 6am to 9am. About 24% of passengers prefer this time window. Many major carriers, including United Airlines, Air Canada and Alaska Airlines, offer flights during this window. This timing works well because it allows you to get an early start on your travel day and arrive in Calgary with plenty of time.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
Direct flights from ORD to YYC usually take about 4 hours, traveling roughly 1,382 miles. If you opt for a connecting flight, expect to add around 5 hours to your journey. 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.)?
Select the "Business class" and "First class" filters when looking for ORD to YYC flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How much is a business class flight from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.)?
A direct, round-trip business class ticket from Chicago, IL (ORD-O'Hare Intl.) to Calgary, AB (YYC-Calgary Intl.) typically costs between 3,078 CAD - 4,610 CAD. A non-stop, one-way business class flight is usually around 1,202 CAD - 1,694 CAD. 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. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Anaa (AAA) (AAA) to Toronto, ON (YYZ-Pearson Intl.) (YYZ) if you opt for a connecting flight.
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 directly 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.) flight and hotel package 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
CA $320
Distance
2211 km
Average flight time
2 hours 56 mins

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Chicago to Calgary Flights

The easy way to book your flights from Chicago to Calgary 

With Expedia, it’s simple to find and book flights to Calgary from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Calgary Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Calgary today, tomorrow, or this week.  

 

Save dollars with cheap flights from O'Hare Intl., ORD to Calgary Intl., YYC 

Sort your search results by price to find great deals on your flight from Chicago to Calgary—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Calgary from Chicago currently is just CA $321 rising to CA $365.  

Here are more money-saving tips: 

  • Fly in May when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Calgary  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Calgary from Chicago 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Calgary with Expedia today.

Chicago to Calgary Flights

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