S$101 Cheap Flights from Chicago to Calgary

View S$101 flight on Tue, 20 Jan, 2026Opens in a new window

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

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Calgary (ORD-YYC)

Prices were available within the past 7 days and start at S$101 for one-way flights and S$255 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$255 Return, found 20 hours ago
S$255
Return
found 20 hours ago
Select United flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$255 found 20 hours ago
United
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$260 Return, found 20 hours ago
S$260
Return
found 20 hours ago
Select United flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$260 found 20 hours ago
United
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$260 Return, found 20 hours ago
S$260
Return
found 20 hours ago
Select United flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$260 found 20 hours ago
Air Canada
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$269 Return, found 20 hours ago
S$269
Return
found 20 hours ago
Select Air Canada flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$269 found 20 hours ago
Air Canada
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$277 Return, found 20 hours ago
S$277
Return
found 20 hours ago
Select Air Canada flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$277 found 20 hours ago
United
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$279 Return, found 20 hours ago
S$279
Return
found 20 hours ago
Select United flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$279 found 20 hours ago
United
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$285 Return, found 20 hours ago
S$285
Return
found 20 hours ago
Select United flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$285 found 20 hours ago
United
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$287 Return, found 20 hours ago
S$287
Return
found 20 hours ago
Select United flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$287 found 20 hours ago
Delta
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$318 Return, found 20 hours ago
S$318
Return
found 20 hours ago
Select Delta flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$318 found 20 hours ago
American Airlines
Tue, 20 Jan - Thu, 22 Jan
ORD
Chicago
YYC
Calgary
S$394 Return, found 20 hours ago
S$394
Return
found 20 hours ago
Select American Airlines flight, departing Tue, 20 Jan from Chicago to Calgary, returning Thu, 22 Jan, priced at S$394 found 20 hours ago

Black Friday Sale

Save up to 50% on select hotels
Book now

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

October is typically the cheapest month to fly

From S$211 - S$437 per traveller.
Chicago to Calgary route information
Origin airport
O'Hare Intl.
Destination airport
Calgary Intl.
Airlines serving
Air Canada, American Airlines, Delta, United
Return price
S$254
Distance
2211 km
Average flight time
2 hours 52 mins

Flights from Chicago to Calgary

There are several airlines that operate frequent flights from Chicago (ORD) to Calgary (YYC) including

The earliest flight leaves O'Hare Intl. Airport at 08:55 and arrives at Calgary Intl. Airport at 11:44. The last flight of the day departs Chicago at 20:19 and arrives at Calgary at 23:29.

The flight distance from Chicago to Calgary is about 2235 km, the shortest flight is 03 hours 45 minutes with WestJet.

Expedia lets you search across the largest number of airlines and Calgary flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Chicago Calgary flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago to Calgary trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Calgary flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Chicago to Calgary with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from O'Hare Airport to YYC?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip flight between O'Hare Airport and YYC Calgary International Airport was S$255. Fares this good don't wait forever, so make sure you book yours today. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to YYC Calgary International Airport?
Each air carrier has different terms and conditions. If you decide to cancel your getaway, visit our Customer Service Portal.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to YYC 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 ORD to Calgary Intl. Airport (YYC) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from ORD to Calgary Intl. Airport (YYC)?
Expect to be cruising at altitude for a while, as the flight distance from Chicago to Calgary is 2,200 kilometres. Set up a playlist of your favourite songs before you leave home to keep yourself entertained during the journey.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to YYC Calgary International Airport?
Flying directly from ORD to YYC Calgary International Airport is a cinch with United Airlines (UA). This top carrier offers 30 flights every month.
Are O'Hare Intl. Airport (ORD) to YYC flight tickets cheaper when they're purchased at the last minute?
Last-minute bookings from ORD to YYC can be hit-or-miss. You may be able to score a bargain, but you could also completely miss out! If you'd prefer to play it safe and start your trip planning ahead of time, Expedia compares flight deals up to 12 months in advance. Just remember that not all airlines publish their prices so far in advance. Our suggestion? Check back often as updates are made frequently.

Explore a world of travel with Expedia

*Available to Expedia members.