S$148 Cheap Flights from Calgary to Chicago

View S$148 flight on Wed, 11 Jun, 2025Opens in a new window

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Cheap Flights from Calgary to Chicago (YYC-ORD)

Prices were available within the past 7 days and start at S$148 for one-way flights and S$301 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, 2 May - Sun, 11 May
YYC
Calgary
ORD
Chicago
S$301 Return, found 1 day ago
S$301
Return
found 1 day ago
Select American Airlines flight, departing Fri, 2 May from Calgary to Chicago, returning Sun, 11 May, priced at S$301 found 1 day ago
Air Canada
Fri, 2 May - Sun, 11 May
YYC
Calgary
ORD
Chicago
S$305 Return, found 1 day ago
S$305
Return
found 1 day ago
Select Air Canada flight, departing Fri, 2 May from Calgary to Chicago, returning Sun, 11 May, priced at S$305 found 1 day ago
Delta
Fri, 2 May - Sun, 11 May
YYC
Calgary
ORD
Chicago
S$308 Return, found 1 day ago
S$308
Return
found 1 day ago
Select Delta flight, departing Fri, 2 May from Calgary to Chicago, returning Sun, 11 May, priced at S$308 found 1 day ago
Air Canada
Fri, 2 May - Sun, 11 May
YYC
Calgary
ORD
Chicago
S$312 Return, found 1 day ago
S$312
Return
found 1 day ago
Select Air Canada flight, departing Fri, 2 May from Calgary to Chicago, returning Sun, 11 May, priced at S$312 found 1 day ago
Delta
Fri, 2 May - Mon, 5 May
YYC
Calgary
ORD
Chicago
S$313 Return, found 1 day ago
S$313
Return
found 1 day ago
Select Delta flight, departing Fri, 2 May from Calgary to Chicago, returning Mon, 5 May, priced at S$313 found 1 day ago
United
Fri, 2 May - Mon, 5 May
YYC
Calgary
ORD
Chicago
S$315 Return, found 1 day ago
S$315
Return
found 1 day ago
Select United flight, departing Fri, 2 May from Calgary to Chicago, returning Mon, 5 May, priced at S$315 found 1 day ago
Air Canada
Fri, 2 May - Mon, 5 May
YYC
Calgary
ORD
Chicago
S$315 Return, found 1 day ago
S$315
Return
found 1 day ago
Select Air Canada flight, departing Fri, 2 May from Calgary to Chicago, returning Mon, 5 May, priced at S$315 found 1 day ago
United
Fri, 2 May - Mon, 5 May
YYC
Calgary
ORD
Chicago
S$323 Return, found 1 day ago
S$323
Return
found 1 day ago
Select United flight, departing Fri, 2 May from Calgary to Chicago, returning Mon, 5 May, priced at S$323 found 1 day ago
Air Canada
Fri, 2 May - Mon, 5 May
YYC
Calgary
ORD
Chicago
S$324 Return, found 1 day ago
S$324
Return
found 1 day ago
Select Air Canada flight, departing Fri, 2 May from Calgary to Chicago, returning Mon, 5 May, priced at S$324 found 1 day ago
WestJet
Fri, 2 May - Sun, 11 May
YYC
Calgary
ORD
Chicago
S$712 Return, found 1 day ago
S$712
Return
found 1 day ago
Select WestJet flight, departing Fri, 2 May from Calgary to Chicago, returning Sun, 11 May, priced at S$712 found 1 day ago
Calgary to Chicago route information
Origin airport
Calgary Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, United, WestJet
Return price
S$300
Distance
2211 km

Flights from Calgary to Chicago

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

The earliest flight leaves Calgary Intl. Airport at 07:00 and arrives at O'Hare Intl. Airport at 11:26. The last flight of the day departs Calgary at 15:35 and arrives at Chicago at 20:10.

The flight distance from Calgary to Chicago is about 2235 km, the shortest flight is 03 hours 18 minutes with WestJet.

Expedia lets you search across the largest number of airlines and Chicago 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 Calgary Chicago 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 Calgary to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chicago 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 Calgary to Chicago 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 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$301. 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.

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