Cheap Flights from Calgary (YYC) to Chicago (ORD)

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

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Frequently asked questions

How long does it take to fly from YYC to O'Hare Airport?
A direct flight with United Airlines takes about 3 hours and 30 minutes. Grab a seat on the 8:30AM flight from YYC Calgary International Airport and come in to land at ORD at 1:00PM. Get your hands on an amazing deal on this and other routes when you use Expedia to book your trip.
Is it cheaper to buy a plane ticket from YYC to O'Hare Intl. Airport (ORD) last minute?
Booking your journey from YYC to ORD last minute could save you a tidy sum if you strike it lucky and find an epic deal. However, airfares generally don't get cheaper as the departure date nears. If you take a wait-and-see approach, flights could also be sold out or the best seats taken (we hope you like the middle seat!). If you want to be on the safe side, book well in advance of the date you want to leave. In fact, you can find some of the biggest deals up to 12 months in advance. If your preferred carrier hasn't released tickets yet, check back regularly as offers are updated on Expedia constantly.
What airports do you fly into for Chicago from Calgary?
O'Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT) are your choices when flying from Calgary to Chicago. Around 26 kilometers northwest of the center of Chicago, O'Hare Intl. Airport (ORD) is the city's main hub. Think about things such as flight departure and arrival times and the distance to your hotel before choosing an airport. Wrigley Field and Millennium Park are a couple of top attractions to check out when you arrive at your destination.
What are the most popular departure times for flights from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
For United Airlines flights from YYC to O'Hare Intl. Airport (ORD), the most popular departure times are between 12:00 PM - 1:00 PM. If you want to avoid those frustrating delays, book a morning flight. This way you can dodge air traffic that accumulates later in the day.
Can I change the date of my flight from Calgary Intl. Airport (YYC) to O'Hare Airport?
It's a piece of cake to make amendments to your YYC to ORD trip yourself. Simply go to the Expedia Trips portal and click on "change flight." Search for new flights and secure the one that better suits your plans. You'll get an estimate of any flight change fees. You can also find your way to our Customer Service portal to chat to our Virtual Agent and get answers to your questions.

Travel information

Travel information

Origin airport
Calgary Intl.
Destination airport
O'Hare Intl.
Distance
2211 km
Average flight time
4 hours 27 mins

Book with confidence

Book with confidence

Calgary to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Calgary to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Calgary to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Calgary to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia