S$192 Cheap Flights from Calgary to Chicago

View S$192 flight on Wed, 6 May, 2026Opens 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 S$192 for one-way flights and S$352 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$352 Return, found 3 days ago
S$352
Return
found 3 days ago
Select Air Canada flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$352 found 3 days ago
Air Canada
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$384 Return, found 3 days ago
S$384
Return
found 3 days ago
Select Air Canada flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$384 found 3 days ago
Air Canada
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$389 Return, found 3 days ago
S$389
Return
found 3 days ago
Select Air Canada flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$389 found 3 days ago
Air Canada
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$415 Return, found 3 days ago
S$415
Return
found 3 days ago
Select Air Canada flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$415 found 3 days ago
Air Canada
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$420 Return, found 3 days ago
S$420
Return
found 3 days ago
Select Air Canada flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$420 found 3 days ago
Air Canada
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$421 Return, found 3 days ago
S$421
Return
found 3 days ago
Select Air Canada flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$421 found 3 days ago
Air Canada
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$451 Return, found 3 days ago
S$451
Return
found 3 days ago
Select Air Canada flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$451 found 3 days ago
Delta
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$459 Return, found 3 days ago
S$459
Return
found 3 days ago
Select Delta flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$459 found 3 days ago
American Airlines
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$718 Return, found 3 days ago
S$718
Return
found 3 days ago
Select American Airlines flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$718 found 3 days ago
WestJet
Thu, 9 Jul - Sat, 18 Jul
YYC
Calgary
ORD
Chicago
S$735 Return, found 3 days ago
S$735
Return
found 3 days ago
Select WestJet flight, departing Thu, 9 Jul from Calgary to Chicago, returning Sat, 18 Jul, priced at S$735 found 3 days ago

Frequently asked questions

How much is a flight from YYC to O'Hare Airport?
Based on airfares available within the last 7 days on Expedia for flights departing within the next year, round-trip flights between YYC Calgary International Airport and O'Hare Intl. Airport (ORD) start from S$352. Make your booking ASAP to secure the best price for your trip. 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 ORD?
We get that things come up unexpectedly, so we've made it as easy as possible for you to cancel your trip online. Just visit the Customer Service Portal and follow the instructions.
How do I find cheap flights from Calgary Intl. Airport (YYC) to ORD 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 O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Calgary Intl. Airport (YYC) to O'Hare Airport?
Around 2,200 kilometres separates Calgary and Chicago, so pack some in-flight entertainment to help you while away a couple of hours. That latest bestseller you've yet to start will be perfect.
Which airlines fly direct from YYC to O'Hare Airport?
Check out the deals on offer with United Airlines (UA) if you want to travel straight from YYC Calgary International Airport to O'Hare Airport. This top carrier offers 30 flights monthly, so you're sure to find one that suits your schedule.
Are Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from YYC Calgary International Airport to O'Hare Airport at the last minute could save you some cash. However, it might cost you a whole lot more! If you'd prefer not to take any chances, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred carrier hasn't released tickets yet, check back often as deals are updated on Expedia all the time.

Travel information

Origin airport
Calgary Intl.
Destination airport
O'Hare Intl.
Return price
S$352
Distance
2211 km
Average flight time
4 hours 32 mins

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