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

Popular airlines from Calgary International Airport (YYC) to Chicago, IL (DPA-Dupage)

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Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $492
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $492
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $725
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $725

Frequently asked questions

How much does a flight from Calgary Intl. Airport (YYC) to Dupage Airport (DPA) cost?
Snag a cheap one-way flight or cheap return flight from Calgary Intl. Airport (YYC) to Dupage Airport (DPA) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Calgary Intl. Airport (YYC) to Dupage Airport (DPA)?
The cheapest month to fly from YYC to DPA is , when demand is low. Off-peak season is typically when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from Calgary Intl. Airport (YYC) to Dupage Airport (DPA)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest YYC to DPA flight.
How many flights per day from Calgary Intl. Airport (YYC) to Dupage Airport (DPA)?
There aren't any daily direct flights available from Calgary Intl. Airport (YYC) to Dupage Airport (DPA). But you can book flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from YYC to DPA?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Calgary Intl. Airport (YYC) to Dupage Airport (DPA)?
To land at Dupage Airport (DPA) on time, book a flight that takes off from Calgary Intl. Airport (YYC) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Calgary Intl. Airport (YYC)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Calgary Intl. Airport (YYC). Compare your options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Calgary Intl. Airport (YYC) to Dupage Airport (DPA) last-minute?
Holding off until just before your departure to book a ticket from YYC to DPA generally means paying more. While it's possible to find some last-minute discounts, they aren't always guaranteed. Keep your travel schedule open to maximize your chances of getting a bargain.
Is it cheaper to book a YYC to DPA flight and hotel package?
Securing a YYC to DPA flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our extensive range of stays and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Calgary Intl. Airport (YYC) to Dupage Airport (DPA)?
In most instances, you're able to cancel or reschedule your YYC to DPA flight. However, additional charges may apply, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you need further details, go to our Customer Service portal.

Travel information

Origin airport
Calgary Intl.
Destination airport
Dupage
Distance
1370 mi

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Calgary to Chicago Flights

The cheapest times to fly from Calgary to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Calgary to Chicago are during the month of . You can find some of the cheapest flights from Calgary to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Calgary to Chicago

Sunday is one of the best days to book for cheap flights from Calgary to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Calgary to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Calgary to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Calgary to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Calgary to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Calgary to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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