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Cayman Islands

$138+ Cheap flights from Westchester County to the Cayman Islands

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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — GCM
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheap flight deals from Westchester County to Cayman Islands

Keep the following information in mind while searching for Westchester County to Cayman Islands flight deals. Data was last updated June 18, 2025.

Round-trip from

$384
(American Airlines)

One-way from

$138
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$416
From Westchester County to Cayman Islands
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One-way flight from Westchester County to Cayman Islands
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Highest demand for flights based on searches. 6% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Westchester County to Cayman Islands

Cheapest flights from Westchester County to Cayman Islands
Explore the most affordable flight options available from Westchester County to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This American Airlines deal was found by Cheapflights users on 6/17. 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 8/116:54 pmHPN - GCM
2 stops19h 18mAmerican Airlines
Mon 8/1812:25 pmGCM - HPN
1 stop6h 35mAmerican Airlines
Deal found 6/17$384
This Delta deal was found by Cheapflights users on 6/16. 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.
Thu 7/316:00 amHPN - GCM
1 stop6h 22mDelta
Thu 8/712:37 pmGCM - HPN
1 stop8h 47mDelta
Deal found 6/16$494
This WestJet deal was found by Cheapflights users on 6/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2612:49 pmHPN - GCM
2 stops48h 56mWestJet
Tue 7/11:45 pmGCM - HPN
2 stops25h 00mWestJet
Deal found 6/17$3,198

Cheapflights Fare Finder

Customize your flight search to find flights from Westchester County to Cayman Islands 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 June 18, 2025.
Use the filters below to find and compare flights from Westchester County to the Cayman Islands that are best for you.

Fly from

Westchester County

Fly to

Cayman Islands

Route

Depart

Return

Price

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Mon 8/11

6:54 pm-1:12 pm

2 stops19h 18m

George Town Owen Roberts Intl

Mon 8/18

12:25 pm-8:00 pm

1 stop6h 35m

$384

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 7/31

6:00 am-11:22 am

1 stop6h 22m

George Town Owen Roberts Intl

Thu 8/7

12:37 pm-10:24 pm

1 stop8h 47m

$494

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 7/15

5:29 pm-11:10 am

2 stops18h 41m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/18

Best time to book a flight from Westchester County to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands 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 the Cayman Islands
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated June 18, 2025.
To help decide which airline to fly from Westchester County to Cayman Islands, see what other customers have to say about 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
8.0
Very good
7,964 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

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
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

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
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

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 Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

  • How can I find direct flights from Westchester County to Cayman Islands?

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

  • Can I find deals for business class flights from Westchester County to Cayman Islands?

    Yes. Cheapflights offers flight deals from Westchester County to Cayman Islands 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 Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Westchester County to Cayman Islands (average of $467). Flying from Westchester County to Cayman Islands in March is currently the most expensive (average of $594). 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 airline flying from Westchester County to Cayman Islands

Discover the top airline that operate flights from Westchester County to Cayman Islands. 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$383Average$459FlexibilityNo cancel feeOn-time71%

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