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Cayman Islands

$120+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — GCM
ago. 11 — ago. 181
lun. 8/11
lun. 8/18
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 agosto 6, 2025.

Round-trip from

$336
(American Airlines)

One-way from

$120
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$476
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 ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 6, 2025.

This American Airlines deal was found by Cheapflights users on 8/5. 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.
sáb. 9/206:50 pmHPN - GCM
2 stops17h 20mAmerican Airlines
sáb. 9/2712:25 pmGCM - HPN
1 stop6h 35mAmerican Airlines
Deal found 8/5$336
This American Airlines deal was found by Cheapflights users on 8/5. 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.
dom. 9/76:59 pmHPN - GCM
2 stops17h 11mAmerican Airlines
dom. 9/1412:28 pmGCM - HPN
2 stops22h 01mAmerican Airlines
Deal found 8/5$341
This American Airlines deal was found by Cheapflights users on 8/5. 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.
mar. 8/266:54 pmHPN - GCM
1 stop17h 26mAmerican Airlines
vie. 8/292:10 pmGCM - HPN
2 stops20h 18mAmerican Airlines
Deal found 8/5$343
This American Airlines deal was found by Cheapflights users on 8/5. 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.
jue. 9/116:59 pmHPN - GCM
1 stop17h 26mAmerican Airlines
dom. 9/1412:28 pmGCM - HPN
2 stops19h 54mAmerican Airlines
Deal found 8/5$348
This American Airlines deal was found by Cheapflights users on 8/5. 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.
sáb. 11/86:49 pmHPN - GCM
1 stop17h 51mAmerican Airlines
sáb. 11/154:10 pmGCM - HPN
1 stop6h 37mAmerican Airlines
Deal found 8/5$384
This Delta deal was found by Cheapflights users on 8/6. 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.
jue. 12/46:00 amHPN - GCM
1 stop6h 37mDelta
mar. 12/92:02 pmGCM - HPN
1 stop7h 36mDelta
Deal found 8/6$465
This Delta deal was found by Cheapflights users on 8/4. 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.
sáb. 8/306:00 amHPN - GCM
1 stop6h 37mDelta
sáb. 9/612:52 pmGCM - HPN
1 stop8h 31mDelta
Deal found 8/4$576

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 agosto 6, 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

sáb. 9/20

6:50 pm-11:10 am

2 stops17h 20m

George Town Owen Roberts Intl

sáb. 9/27

12:25 pm-8:00 pm

1 stop6h 35m

$336

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

dom. 9/7

6:59 pm-11:10 am

2 stops17h 11m

George Town Owen Roberts Intl

dom. 9/14

12:28 pm-11:29 am

2 stops22h 01m

$341

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

mar. 8/26

6:54 pm-11:20 am

1 stop17h 26m

George Town Owen Roberts Intl

vie. 8/29

2:10 pm-11:28 am

2 stops20h 18m

$343

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

jue. 9/11

6:59 pm-11:25 am

1 stop17h 26m

George Town Owen Roberts Intl

dom. 9/14

12:28 pm-9:22 am

2 stops19h 54m

$348

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

sáb. 11/8

6:49 pm-12:40 pm

1 stop17h 51m

George Town Owen Roberts Intl

sáb. 11/15

4:10 pm-10:47 pm

1 stop6h 37m

$384

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

jue. 12/4

6:00 am-12:37 pm

1 stop6h 37m

George Town Owen Roberts Intl

mar. 12/9

2:02 pm-9:38 pm

1 stop7h 36m

$465

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

sáb. 8/30

6:00 am-11:37 am

1 stop6h 37m

George Town Owen Roberts Intl

sáb. 9/6

12:52 pm-10:23 pm

1 stop8h 31m

$576

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

mar. 12/9

7:42 pm-12:05 pm

1 stop16h 23m

$120

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

mié. 12/10

7:42 pm-4:31 pm

1 stop20h 49m

$133

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

dom. 11/23

6:00 am-12:37 pm

1 stop6h 37m

$418

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

Showing 1-10 of 13 results
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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 agosto 6, 2025.
See what other customers who have flown with Delta, American Airlines, and WestJet from Westchester County to the Cayman Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,985 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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
7,985 reviews
Delta
8.0
Very good
7,985 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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
7,985 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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.
WestJet
7.2
Good
3,003 reviews
Delta
8.0
Very good
7,985 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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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Alternative routes for Westchester County to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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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 agosto 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$383Average$529FlexibilityNo cancel feeOn-time71%

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