CA $155 Cheap Flights from Calgary (YYC) to Chicago (ORD)

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

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

Prices were available within the past 7 days and start at CA $155 for one-way flights and CA $238 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
United
Air Canada
United
Air Canada
WestJet
United
United
American Airlines
Delta

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

May is typically the cheapest month to fly

From CA $204 - CA $499 per traveller.

Graph displaying average flight prices per month

Flight from Calgary to Chicago (YYC - ORD) route information
Origin airport
Calgary Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Alaska Airlines, American Airlines, Delta, United, WestJet
Roundtrip price
CA $237
Distance
2211 km
Average flight time
4 hours 28 mins

Calgary to Chicago Flights

The easy way to book your flights from Calgary to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Calgary whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Calgary to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Calgary Intl., YYC to O'Hare Intl., ORD 

Sort your search results by price to find great deals on your flight from Calgary to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Calgary currently is just CA $238 rising to CA $309.  

Here are more money-saving tips: 

  • Fly in September when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Calgary 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Frequently asked questions

How much is a flight from Calgary Intl. Airport (YYC) to ORD?
Start packing your bags, because round-trip flights from Calgary Intl. Airport (YYC) to ORD start from CA $238. That's based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices can move quickly, so book today to nab the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
We understand that life can throw the odd curveball, so we've made it as simple 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 YYC to O'Hare Airport that have flexible change policies?
Flights from Calgary Intl. Airport (YYC) to ORD offering flexible change policies are available from several carriers. Simply use our "No change fees" filter while searching. You'll only need to pay the cost difference between the two flights, with no added fees to worry about.
How many hours is the flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)?
The flight time from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD) is around 7 hours and 5 minutes. Put your earphones in, listen to your favourite podcast and the hours will whiz by.
How far is the flight from YYC Calgary International Airport to O'Hare Intl. Airport (ORD)?
The flying distance between YYC Calgary International Airport (YYC) and O'Hare Airport (ORD) is 2,200 kilometres. Sneak in a nap or bury your nose in a book and the trip will zip on by.
Which airlines fly direct from YYC to ORD?
Flying nonstop from YYC Calgary International Airport to ORD is a breeze with United Airlines (UA). This top carrier operates 30 flights every month.
Are YYC to ORD flight tickets cheaper when they're purchased at the last minute?
It is possible to score great last-minute deals from YYC Calgary International Airport to O'Hare Intl. Airport (ORD), but it's also possible to miss out entirely! As many airlines release seats up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to pounce when you spot a good bargain. Expedia compares carrier prices and updates flight deals frequently, so you can feel confident knowing you're always seeing the latest offers.

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