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Key West

$186+ Cheap flights from Westchester County to Key West (EYW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — EYW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Westchester County to Key West

Cheapest flights from Westchester County to Key West
Explore the most affordable flight options available from Westchester County to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1510:05 amHPN - EYW
1 stop6h 08mAmerican Airlines
Sat 11/224:53 pmEYW - HPN
1 stop5h 54mAmerican Airlines
Deal found 10/28$379
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/61:36 pmHPN - EYW
1 stop8h 14mAmerican Airlines
Mon 12/87:00 amEYW - HPN
2 stops11h 09mAmerican Airlines
Deal found 10/28$381
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:00 amHPN - EYW
1 stop8h 03mDelta
Tue 11/187:40 amEYW - HPN
1 stop6h 48mDelta
Deal found 10/30$442
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1410:05 amHPN - EYW
2 stops6h 56mAmerican Airlines
Tue 11/1811:17 amEYW - HPN
1 stop6h 56mAmerican Airlines
Deal found 10/30$447
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:29 amHPN - EYW
1 stop6h 46mDelta
Thu 12/183:02 pmEYW - HPN
1 stop7h 07mDelta
Deal found 10/28$505
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/157:30 amHPN - EYW
2 stops9h 27mAmerican Airlines
Thu 12/184:40 pmEYW - HPN
1 stop6h 20mAmerican Airlines
Deal found 10/28$510

Cheap flight deals from Westchester County to Key West

Keep the following information in mind while searching for Westchester County to Key West flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$297
(American Airlines)

One-way from

$186
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$454
Provider with most accurate pricing for New York (NYC)-Key West flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Key West flights.
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From Westchester County to Key West
Search Deals
One-way flight from Westchester County to Key West
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Westchester County to Key West that are best for you.

Fly from

Westchester County

Fly to

Key West

Route

Depart

Return

Price

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Sat 1/31

5:30 pm-11:56 pm

1 stop6h 26m

Key West

Sat 2/7

4:37 pm-10:59 pm

1 stop6h 22m

$297

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Thu 1/1

7:00 am-1:13 pm

1 stop6h 13m

Key West

Wed 1/7

11:18 am-6:08 pm

1 stop6h 50m

$328

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Wed 2/18

1:30 pm-10:59 pm

2 stops9h 29m

Key West

Mon 2/23

12:03 pm-8:07 pm

1 stop8h 04m

$372

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Sat 11/15

6:30 am-4:13 pm

2 stops9h 43m

Key West

Sat 11/22

4:53 pm-10:47 pm

1 stop5h 54m

$384

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Sat 12/6

3:00 pm-11:07 pm

2 stops8h 07m

Key West

Mon 12/8

7:00 am-6:09 pm

2 stops11h 09m

$386

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Tue 12/2

8:00 am-11:20 am

2 stops51h 20m

$186

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Tue 11/11

12:09 pm-10:07 am

2 stops21h 58m

$191

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Sat 11/8

1:29 pm-7:46 pm

2 stops30h 17m

$225

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Sat 11/8

8:00 am-8:15 am

3 stops48h 15m

$240

White PlainsKey West

HPN - EYW

HPNEYW

White Plains Westchester County

Tue 11/11

6:00 am-11:31 am

1 stop5h 31m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 14 results
1
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Best time to book a flight from Westchester County to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Westchester County with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Westchester County to Key West

What is the cheapest month to book a flight from Westchester County to Key West?

Currently, March is the cheapest month in which you can book a flight from Westchester County to Key West (average of $232). Flying from Westchester County to Key West in May is currently the most expensive (average of $521). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated October 30, 2025.
Read through reviews of airlines operating flights from Westchester County to Key West, such as Delta and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Key West from Westchester County?

    Key West (EYW), located 2.6 mi from the city center, is the airport you fly into when you book flights from Westchester County to Key West.

  • How long is the flight from Westchester County to Key West?

    Departing from Westchester County to Key West will take you 6h 26m. There are 1231 mi between Westchester County and Key West.

  • Can I find deals for flights from Westchester County to Key West that include hotel bookings?

    Yes. In addition to deals on Westchester County to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Westchester County to Key West.

  • Can I find deals for business class flights from Westchester County to Key West?

    Yes. Cheapflights offers flight deals from Westchester County to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Westchester County to Key West?

    Currently, March is the cheapest month in which you can book a flight from Westchester County to Key West (average of $232). Flying from Westchester County to Key West in May is currently the most expensive (average of $521). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 2 airlines flying from Westchester County to Key West

Discover the top 2 airlines that operate flights from Westchester County to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$263Average$655FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$313Average$541FlexibilityNo cancel feeOn-time71%

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