$104 Cheap Flights from Calgary (YYC) to Chicago (ORD)

View $104 flight on Fri, Dec 26, 2025Opens in a new window

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

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Cheap Flights from Calgary to Chicago (YYC-ORD)

Prices were available within the past 7 days and start at $104 for one-way flights and $156 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Mon, Dec 22 - Mon, Jan 5
YYC
Calgary
ORD
Chicago
$156 Roundtrip, found 3 days ago
$156
Roundtrip
found 3 days ago
Select WestJet flight, departing Mon, Dec 22 from Calgary to Chicago, returning Mon, Jan 5, priced at $156 found 3 days ago
WestJet
Fri, Dec 26 - Mon, Jan 5
YYC
Calgary
ORD
Chicago
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Dec 26 from Calgary to Chicago, returning Mon, Jan 5, priced at $157 found 3 days ago
Air Canada
Thu, Dec 25 - Wed, Jan 7
YYC
Calgary
ORD
Chicago
$161 Roundtrip, found 15 hours ago
$161
Roundtrip
found 15 hours ago
Select Air Canada flight, departing Thu, Dec 25 from Calgary to Chicago, returning Wed, Jan 7, priced at $161 found 15 hours ago
WestJet
Mon, Dec 22 - Mon, Jan 5
YYC
Calgary
ORD
Chicago
$163 Roundtrip, found 15 hours ago
$163
Roundtrip
found 15 hours ago
Select WestJet flight, departing Mon, Dec 22 from Calgary to Chicago, returning Mon, Jan 5, priced at $163 found 15 hours ago
WestJet
Mon, Jan 5 - Mon, Jan 12
YYC
Calgary
ORD
Chicago
$165 Roundtrip, found 3 days ago
$165
Roundtrip
found 3 days ago
Select WestJet flight, departing Mon, Jan 5 from Calgary to Chicago, returning Mon, Jan 12, priced at $165 found 3 days ago
United
Sat, May 2 - Tue, May 5
YYC
Calgary
ORD
Chicago
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 2 from Calgary to Chicago, returning Tue, May 5, priced at $168 found 1 day ago
WestJet
Mon, Dec 22 - Fri, Jan 9
YYC
Calgary
ORD
Chicago
$171 Roundtrip, found 15 hours ago
$171
Roundtrip
found 15 hours ago
Select WestJet flight, departing Mon, Dec 22 from Calgary to Chicago, returning Fri, Jan 9, priced at $171 found 15 hours ago
Air Canada
Wed, Apr 29 - Tue, May 5
YYC
Calgary
ORD
Chicago
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Apr 29 from Calgary to Chicago, returning Tue, May 5, priced at $173 found 1 day ago
American Airlines
Fri, Apr 24 - Sun, Apr 26
YYC
Calgary
ORD
Chicago
$193 Roundtrip, found 2 days ago
$193
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Apr 24 from Calgary to Chicago, returning Sun, Apr 26, priced at $193 found 2 days ago
Delta
Fri, Dec 12 - Tue, Dec 16
YYC
Calgary
ORD
Chicago
$214 Roundtrip, found 9 hours ago
$214
Roundtrip
found 9 hours ago
Select Delta flight, departing Fri, Dec 12 from Calgary to Chicago, returning Tue, Dec 16, priced at $214 found 9 hours ago

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

May is typically the cheapest month to fly

From $147 - $340 per traveler.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $333
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $333

Frequently asked questions

How much does a flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $104 or cheap return flight from $156 from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from YYC to ORD is December, when demand is low. Off-peak season is often when you'll find cheap fares for travel between these airports.
Which airlines fly direct from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
When departing from Calgary Intl. Airport (YYC), you can board a nonstop flight to O'Hare Intl. Airport (ORD) with United Airlines.
What is the cheapest airline that flies from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline flying from YYC to ORD, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
On average, Calgary Intl. Airport (YYC) only has 1 nonstop flight to O'Hare Intl. Airport (ORD) each day. For more choices, try Expedia's easy-to-use filter tool. Enter your dates of travel, then choose "1 Stop" or "2+ Stops" to discover flights with layovers.
What are the most popular departure times for flights from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
The 12 PM departures from YYC to ORD are typically the busiest. They can also be more expensive. If you're looking to save, book during off-peak hours.
What day of the week has the most flights from YYC to ORD?
Friday has the most flights from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD). Consider leaving on this day and you'll have a greater chance of finding a schedule that works for you.
What is the earliest flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
Calgary Intl. Airport (YYC)'s earliest flight to O'Hare Intl. Airport (ORD) leaves at approximately 12:41PM UTC-7. With a total journey time of 3h 34m, you'll land at around 5:15PM UTC-6.
How long does it take to fly from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
Flights from YYC to ORD have an average travel time of 3 hours and 34 minutes. The total distance between these two airports is 1,400 mi.
What airline has the least delays from YYC to ORD?
Consider booking with American Airlines if you'd like to go straight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD) without any delays. This airline has the best track record for punctuality, with an on-time score of 89%. Want to be updated if anything changes? You can check your flight status using the Expedia App.
What is the best time to fly from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
Choose a flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the likelihood of delays. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Calgary Intl. Airport (YYC)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Calgary Intl. Airport (YYC). Consider the options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD) last-minute?
Booking your plane ticket from YYC to ORD right before your trip is usually more expensive. However, if you're flexible with your schedule, you could bag a cheap last-minute fare.
Is it cheaper to book a YYC to ORD flight and hotel package?
You'll generally save money by securing a YYC to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After selecting your ideal flights and accommodations, you can add extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
Typically, you can cancel or reschedule your YYC to ORD flight. However, there may be additional charges, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline's fees and guidelines on flight changes, or if you want further information, go to our Customer Service portal.

Travel information

Origin airport
Calgary Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Alaska Airlines, American Airlines, Delta, Porter Airlines, United, WestJet
Roundtrip price
$156
Distance
1381 mi
Average flight time
4 hours 34 mins

Book with confidence

Calgary to Chicago Flights

The cheapest times to fly from Calgary to Chicago

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 Calgary to Chicago are during the month of December. You can find some of the cheapest flights from Calgary to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Calgary to Chicago

Sunday is one of the best days to book for cheap flights from Calgary to Chicago: 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 Calgary to Chicago

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 Calgary to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $104 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 Calgary to Chicago 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 Calgary to Chicago 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.

 

Calgary to Chicago Flights

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*Available to One Key members.