$103 Cheap Air Canada flights Calgary (YYC) to Chicago (ORD)

View $103 flight on Thu, Oct 2, 2025Opens in a new window

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$103 Cheap Air Canada flights Calgary (YYC) to Chicago (ORD)

Prices were available within the past 7 days and start at $103 for one-way flights and $157 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Oct 16 - Sat, Oct 18
YYC
Calgary
ORD
Chicago
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Thu, Oct 16 from Calgary to Chicago, returning Sat, Oct 18, priced at $157 found 4 hours ago
Air Canada
Wed, Oct 15 - Sat, Oct 25
YYC
Calgary
ORD
Chicago
$163 Roundtrip, found 4 hours ago
$163
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Wed, Oct 15 from Calgary to Chicago, returning Sat, Oct 25, priced at $163 found 4 hours ago
Air Canada
Tue, Oct 14 - Wed, Oct 15
YYC
Calgary
ORD
Chicago
$168 Roundtrip, found 4 hours ago
$168
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Tue, Oct 14 from Calgary to Chicago, returning Wed, Oct 15, priced at $168 found 4 hours ago
Air Canada
Thu, Oct 2 - Mon, Oct 6
YYC
Calgary
ORD
Chicago
$170 Roundtrip, just found
$170
Roundtrip
just found
Select Air Canada flight, departing Thu, Oct 2 from Calgary to Chicago, returning Mon, Oct 6, priced at $170 just found
Air Canada
Thu, Oct 16 - Sat, Oct 18
YYC
Calgary
ORD
Chicago
$171 Roundtrip, found 4 hours ago
$171
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Thu, Oct 16 from Calgary to Chicago, returning Sat, Oct 18, priced at $171 found 4 hours ago
Air Canada
Tue, Oct 14 - Sat, Oct 25
YYC
Calgary
ORD
Chicago
$173 Roundtrip, found 4 hours ago
$173
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Tue, Oct 14 from Calgary to Chicago, returning Sat, Oct 25, priced at $173 found 4 hours ago
Flights from Calgary (YYC) to Chicago (ORD)
Origin airport
Calgary Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Alaska Airlines, American Airlines, Delta, United, WestJet
Popular airline
WestJet
Distance
1381 mi
Average flight time
4 hours 28 mins

Frequently asked questions

How much is an Air Canada flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
Make use of the "Price (lowest to highest)" filter on Expedia to search for cheap Air Canada round-trip flights from $157 from YYC to ORD. Affordable one-way options from $103 are available as well.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from YYC to ORD with Air Canada?
Browse for round-trip or one-way flights to Chicago in January or February. You could find an affordable fare with Air Canada during these off-season months.
What is the cheapest time to book flights from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD) with Air Canada?
Start your search for Air Canada flights from YYC to ORD about one month before you want to go. The cheapest time to book an international flight is generally 18 to 29 days ahead of your travel date when you can save 17% versus booking four to five months in advance. Regardless of itinerary and fare class, the best day of the week to book international airfare is usually Sunday. Friday can be the most expensive. Passengers booking on a Sunday can save an average of 17% compared to those who book on a Friday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does Air Canada fly nonstop from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
Use our "Nonstop" filter when looking for direct Air Canada flights from YYC to ORD. It's also an easy way to compare other carriers offering the same nonstop route.
What is the earliest Air Canada flight from YYC to ORD?
Find Air Canada's earliest flights from YYC to ORD by selecting our "Early Morning" and "Morning" filters. Not only will you arrive at your destination sooner, early departures also have a 20% less chance of being canceled.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does Air Canada fly into in Chicago?
Air Canada flights from Calgary Intl. Airport (YYC) to Chicago land at O'Hare Intl. Airport (ORD). This is the main gateway here.
Why fly with Air Canada from YYC to ORD?
Traveling from YYC to ORD with Air Canada means enjoying a range of perks, such as top-tier customer service and a 4-star airline rating. Plus, when booking through Expedia, One Key™ members can earn OneKeyCash™* to spend on select future travel purchases. That's on top of the Air Canada Aeroplan points you can earn with Air Canada.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Air Canada flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
Typically, you can cancel or change your flight, although additional charges may apply if your booking was made over 24 hours ago. Need to keep your options open? Use Expedia's "Changes included" and "No cancel fee" filters to find flights that won't charge extra if you have to adjust your plans. To update your booking, go to "Trips," select your flight and click on "Manage Booking" for more information.
*Available to One Key members.