$124 Cheap Flights from Calgary (YYC) to Chicago (ORD)

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Cheap Flights from Calgary to Chicago (YYC-ORD)

Prices were available within the past 7 days and start at $124 for one-way flights and $200 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Air Canada
WestJet
WestJet
Air Canada
Air Canada
Air Canada
Air Canada
Air Canada
WestJet
Flights from Calgary (YYC) to Chicago (ORD)
Origin airport
Calgary Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Alaska Airlines, American Airlines, Delta, United, WestJet
Roundtrip price
$200
Distance
1381 mi

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 YYC to ORD 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 $124 now!

Frequently asked questions

How long does it take to fly from YYC to O'Hare Intl. Airport (ORD)?
Book a fare with United Airlines and you’ll be traveling for approximately 3 hours and 23 minutes. This well-known airline operates a direct flight that takes off at 7:30AM from YYC and gets to ORD at 11:53AM. Expedia has some of the best deals around, so take a peek at what’s available on this route today.
Is it cheaper to buy a plane ticket from Calgary Intl. Airport (YYC) to O'Hare Airport last minute?
When it comes to booking your flights, being prepared pays dividends. While you may be able to score a deal on a Calgary Intl. Airport (YYC) to O’Hare Intl. Airport (ORD) flight at the last minute, fares usually don’t get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days in advance. For international journeys it’s between three and four months.
What airline has the least delays from YYC to ORD?
Depart with American Airlines from YYC to O’Hare Airport and land at the time found on your plane ticket. This carrier clinches first place on this route, with an on-time score of 92%. If your flight is delayed for some reason, the Expedia App will help you stay updated. Our popular app provides immediate trip alerts, from flight delays to gate changes and more.
Can I find cheap nonstop flights from YYC to ORD in the next three months?
The best price we can find for a roundtrip nonstop flight from Calgary to Chicago in the next 90 days is $201. This amount is based on available flights on Expedia with a departure date within the next three months. This airfare is for a flight via WestJet leaving YYC on June 14 2024 and landing at O’Hare Intl. Airport (ORD), with a return flight on June 16 2024. This price was last updated on June 1 2024.It’s a breeze to find nonstop cheap flights from YYC to O’Hare Airport by using our filters. Start by typing in details of your trip, then click on “Nonstop” under “Filter by” on the left side of the page. Your results will appear with the lowest-priced ticket first. If you don’t need to leave on a certain day, use our “Flexible dates” feature. You’ll be able to compare ticket prices for nearby dates and grab the best deal possible.
What airports do you fly into for Chicago from Calgary?
With O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT) to choose from, connecting from Calgary to Chicago is a cinch. The city’s main terminal, O’Hare Intl. Airport (ORD), is about 16 mi northwest of the downtown area. Along with ticket prices, consider factors like the ease of getting from the airport and the distance to your hotel when deciding where to fly into. Get your Chicago adventure off to a flying start by discovering Wrigley Field and Millennium Park.
What are the most popular departure times for flights from YYC to O'Hare Airport?
Between 2:00 PM - 3:00 PM is when you’ll find the most American Airlines flights jetting from Calgary Intl. Airport (YYC) to O’Hare Intl. Airport (ORD). Our handy tip? Book a flight that departs early. With air traffic yet to build up around airports, your odds of catching a delay-free flight are better.
Can I change the date of my flight from Calgary Intl. Airport (YYC) to O'Hare Airport?
Make changes quickly to your YYC to O’Hare Airport journey through the Expedia Trips portal. But before amending dates or times, browse the rules and conditions in your itinerary to learn what you can do and if fees apply for changes. Some airlines charge a change fee per person, plus any difference in fare prices. But if you booked in the last 24 hours, you may be able to cancel for free and book new flights. You can also visit our Customer Service portal for further information and to chat with our Virtual Agent.
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