Cheap Flights from Chicago (ORD) to Port Bailey (KPY)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY)

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Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY) cost?
Grab a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY)?
Traveling in is a great way to save, as it's the cheapest month for flights between ORD and KPY. You'll often find the lowest fares during the off-season.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY)?
To find the cheapest airline that'll fly you from ORD to KPY, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY)?
Nonstop flights from O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to KPY?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can change depending on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY)?
To avoid possible delays on the O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY) route, aim to fly before 3 PM. Departures after this hour have a 22% higher chance of being canceled.**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.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY) last-minute?
Holding off until right before your break to book your flight from ORD to KPY generally means paying more. While you may find some last-minute offers, they aren't always guaranteed. Allow some flexibility in your schedule for the best chance of getting a bargain.
Is it cheaper to book an ORD to KPY flight and hotel package?
Compared with arranging flights and hotels separately, booking an ORD to KPY flight and hotel package with Expedia could result in significant savings. Better yet, managing everything in one place will take the stress out of travel planning. Just secure your flights and select from our wide range of stays, then tailor your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Port Bailey, AK (KPY)?
If you reserved your ORD to KPY flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for further details.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Port Bailey
Distance
2962 mi

Book with confidence

Chicago to Port Bailey Flights

The cheapest times to fly from Chicago to Port Bailey

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 Chicago to Port Bailey are during the month of . You can find some of the cheapest flights from Chicago to Port Bailey with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Port Bailey

Sunday is one of the best days to book for cheap flights from Chicago to Port Bailey: 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 Chicago to Port Bailey

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 Chicago to Port Bailey in 2025. 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 Chicago to Port Bailey 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 Chicago to Port Bailey 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.

 

Chicago to Port Bailey Flights

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*Available to One Key members.