$226 Cheap Flights from White Plains (HPN) to Key West (EYW)

View $226 flight on Tue, Sep 30, 2025Opens in a new window

Popular airlines from Westchester County Airport (HPN) to Key West Intl. Airport (EYW)

Cheap Flights from White Plains to Key West (HPN-EYW)

Prices were available within the past 7 days and start at $226 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Aug 12 - Tue, Aug 19
HPN
White Plains
EYW
Key West
$249 Roundtrip, just found
$249
Roundtrip
just found
Select Delta flight, departing Tue, Aug 12 from White Plains to Key West, returning Tue, Aug 19, priced at $249 just found
American Airlines
Tue, Apr 21 - Tue, Apr 28
HPN
White Plains
EYW
Key West
$264 Roundtrip, found 11 hours ago
$264
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Apr 21 from White Plains to Key West, returning Tue, Apr 28, priced at $264 found 11 hours ago
Delta
Sat, Nov 15 - Tue, Nov 18
HPN
White Plains
EYW
Key West
$273 Roundtrip, found 4 hours ago
$273
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Nov 15 from White Plains to Key West, returning Tue, Nov 18, priced at $273 found 4 hours ago
American Airlines
Sat, Oct 4 - Thu, Oct 9
HPN
White Plains
EYW
Key West
$278 Roundtrip, found 8 hours ago
$278
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Oct 4 from White Plains to Key West, returning Thu, Oct 9, priced at $278 found 8 hours ago
Delta
Sat, Nov 8 - Thu, Nov 13
HPN
White Plains
EYW
Key West
$288 Roundtrip, found 2 days ago
$288
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 8 from White Plains to Key West, returning Thu, Nov 13, priced at $288 found 2 days ago
American Airlines
Sat, Sep 6 - Thu, Sep 11
HPN
White Plains
EYW
Key West
$293 Roundtrip, found 5 days ago
$293
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Sep 6 from White Plains to Key West, returning Thu, Sep 11, priced at $293 found 5 days ago
Delta
Sat, Sep 27 - Sat, Oct 4
HPN
White Plains
EYW
Key West
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 27 from White Plains to Key West, returning Sat, Oct 4, priced at $297 found 1 day ago
Delta
Wed, Oct 1 - Wed, Oct 8
HPN
White Plains
EYW
Key West
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 1 from White Plains to Key West, returning Wed, Oct 8, priced at $309 found 1 day ago
Delta
Sat, Oct 25 - Thu, Oct 30
HPN
White Plains
EYW
Key West
$318 Roundtrip, found 1 day ago
$318
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 25 from White Plains to Key West, returning Thu, Oct 30, priced at $318 found 1 day ago
Delta
Fri, Oct 31 - Tue, Nov 4
HPN
White Plains
EYW
Key West
$323 Roundtrip, found 1 day ago
$323
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 31 from White Plains to Key West, returning Tue, Nov 4, priced at $323 found 1 day ago

Find the cheapest month to fly from White Plains (HPN) to Key West (EYW)

September is typically the cheapest month to fly

From $217 - $495 per traveler.

Graph displaying average flight prices per month

Flights from White Plains (HPN) to Key West (EYW)
Origin airport
Westchester County
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta
Roundtrip price
$248
Distance
1231 mi

White Plains to Key West Flights

The cheapest times to fly from White Plains to Key West

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 White Plains to Key West are during the month of August. You can find some of the cheapest flights from White Plains to Key West with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from White Plains to Key West

Sunday is one of the best days to book for cheap flights from White Plains to Key West: 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 White Plains to Key West

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 White Plains to Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $226 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 White Plains to Key West 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 White Plains to Key West 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.

 

Frequently asked questions

How much does a flight from Westchester County Airport (HPN) to Key West Intl. Airport (EYW) cost?
Discover the latest flight deals from HPN to EYW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from HPN to EYW?
The cheapest flights from HPN to EYW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from HPN to EYW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from HPN to EYW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Westchester County Airport (HPN) to Key West Intl. Airport (EYW)?
There aren't any daily direct flights departing from Westchester County Airport (HPN) to Key West Intl. Airport (EYW). But you can book flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from HPN to EYW?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can vary based on a number of factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Westchester County Airport (HPN) to Key West Intl. Airport (EYW)?
Opt for a flight from Westchester County Airport (HPN) to Key West Intl. Airport (EYW) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Later departures have a 22% higher chance of being canceled, on average.**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 Westchester County Airport (HPN) to Key West Intl. Airport (EYW) last-minute?
Last-minute bookings from HPN to EYW are generally more expensive. For the best rates, start searching for flights early. That said, if you can play around with your travel dates, it's possible to land a cheap ticket just before your departure.
Is it cheaper to book a HPN to EYW flight and hotel package?
Booking a HPN to EYW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Choose from our impressive range of hotels and then add flights, car rentals and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Westchester County Airport (HPN) to Key West Intl. Airport (EYW)?
If you booked your HPN to EYW flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

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*Available to One Key members.