￥17,963 Cheap Flights from Calgary (YYC) to Chicago (ORD)

View ￥17,963 flight on Thu, Oct 30, 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 ￥17,963 for one-way flights and ￥29,084 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, Feb 13 - Mon, Feb 16
YYC
Calgary
ORD
Chicago
￥29,084 Roundtrip, found 3 days ago
￥29,084
Roundtrip
found 3 days ago
Select United flight, departing Fri, Feb 13 from Calgary to Chicago, returning Mon, Feb 16, priced at ￥29,084 found 3 days ago
WestJet
Fri, Feb 13 - Mon, Feb 16
YYC
Calgary
ORD
Chicago
￥29,084 Roundtrip, found 3 days ago
￥29,084
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Feb 13 from Calgary to Chicago, returning Mon, Feb 16, priced at ￥29,084 found 3 days ago
Air Canada
Fri, Feb 13 - Mon, Feb 16
YYC
Calgary
ORD
Chicago
￥30,064 Roundtrip, found 3 days ago
￥30,064
Roundtrip
found 3 days ago
Select Air Canada flight, departing Fri, Feb 13 from Calgary to Chicago, returning Mon, Feb 16, priced at ￥30,064 found 3 days ago
WestJet
Fri, Feb 13 - Mon, Feb 16
YYC
Calgary
ORD
Chicago
￥31,110 Roundtrip, found 3 days ago
￥31,110
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Feb 13 from Calgary to Chicago, returning Mon, Feb 16, priced at ￥31,110 found 3 days ago
Air Canada
Sun, Oct 12 - Sun, Oct 19
YYC
Calgary
ORD
Chicago
￥31,850 Roundtrip, found 1 day ago
￥31,850
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Oct 12 from Calgary to Chicago, returning Sun, Oct 19, priced at ￥31,850 found 1 day ago
Air Canada
Fri, Feb 13 - Mon, Feb 16
YYC
Calgary
ORD
Chicago
￥32,090 Roundtrip, found 3 days ago
￥32,090
Roundtrip
found 3 days ago
Select Air Canada flight, departing Fri, Feb 13 from Calgary to Chicago, returning Mon, Feb 16, priced at ￥32,090 found 3 days ago
Air Canada
Thu, Oct 16 - Sun, Oct 19
YYC
Calgary
ORD
Chicago
￥32,830 Roundtrip, found 1 day ago
￥32,830
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Oct 16 from Calgary to Chicago, returning Sun, Oct 19, priced at ￥32,830 found 1 day ago
Delta
Mon, Oct 13 - Wed, Oct 15
YYC
Calgary
ORD
Chicago
￥33,050 Roundtrip, found 5 days ago
￥33,050
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Oct 13 from Calgary to Chicago, returning Wed, Oct 15, priced at ￥33,050 found 5 days ago
Air Canada
Sun, Oct 12 - Wed, Oct 15
YYC
Calgary
ORD
Chicago
￥33,430 Roundtrip, found 1 day ago
￥33,430
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Oct 12 from Calgary to Chicago, returning Wed, Oct 15, priced at ￥33,430 found 1 day ago
Air Canada
Fri, Feb 13 - Mon, Feb 16
YYC
Calgary
ORD
Chicago
￥33,574 Roundtrip, found 3 days ago
￥33,574
Roundtrip
found 3 days ago
Select Air Canada flight, departing Fri, Feb 13 from Calgary to Chicago, returning Mon, Feb 16, priced at ￥33,574 found 3 days ago

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

May is typically the cheapest month to fly

From ￥21,643 - ￥50,451 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from ￥34,200
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from ￥34,200
Flights from Calgary (YYC) to Chicago (ORD)
Origin airport
Calgary Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, United, WestJet
Roundtrip price
￥29,084
Distance
2211 km
Average flight time
4 hours 27 mins

Calgary to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Calgary to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with YYC to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Calgary for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from Calgary Intl. Airport (YYC) to ORD?
Pack your bags, because round-trip journeys between YYC Calgary International Airport and ORD start from ￥29,084. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can rise quickly, so book now to nab the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from YYC Calgary International Airport to O'Hare Intl. Airport (ORD)?
The majority of flights can be canceled online, but every air carrier has different terms and conditions. If you do need to cancel your flight, go to our Customer Service Portal and follow the instructions.
How do I find cheap flights from YYC to O'Hare Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for YYC Calgary International Airport to ORD flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from YYC to O'Hare Airport?
There are plenty of ways to make the 3 hours and 23 minutes between YYC and ORD go by quicker. If you want to be productive, sort through your camera roll or clear out all those unwanted emails. A good snooze also helps pass the time!
How far is the flight from YYC Calgary International Airport to O'Hare Intl. Airport (ORD)?
Around 2,200 kilometers separates Calgary and Chicago, so pack something to help you while away a couple of hours. That novel you're eager to read will be just the ticket.
Which airlines fly direct from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
One airline that services the route from YYC Calgary International Airport to O'Hare Airport is United Airlines (UA). It offers 60 flights every month. American Airlines (AA) is another option. It operates 30 flights each month. Between these two airlines, you'll be able to find a great deal from Calgary to Chicago.
Are YYC Calgary International Airport to ORD flight tickets cheaper when they're purchased at the last minute?
Flight tickets from YYC to O'Hare Airport are available up to a year prior to departure on Expedia. And although you may occasionally score a fantastic last-minute deal, it's not something you should count on. Also, booking your flights in advance means you'll have more choices — and you can avoid getting stuck in the dreaded middle seat! We're always updating our fares to bring you the biggest bargains, so check back often for all the latest specials.

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