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Cayman Islands

$110+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — GCM
Feb 23 — Mar 21
Mon 2/23
Mon 3/2
1 adult, Economy
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Cheap 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 January 24, 2026.

This American Airlines deal was found by Cheapflights users on 1/22. 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 3/96:54 pm
HPN
-
GCM
2 stops17h 11m
American Airlines
Mon 3/162:35 pm
GCM
-
HPN
2 stops19h 54m
American Airlines
Deal found 1/22$306
This Delta deal was found by Cheapflights users on 1/21. 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.
Wed 2/186:00 am
HPN
-
GCM
1 stop6h 29m
Delta
Wed 2/251:54 pm
GCM
-
HPN
1 stop8h 06m
Delta
Deal found 1/21$321
This Delta deal was found by Cheapflights users on 1/21. 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.
Wed 2/186:00 am
HPN
-
GCM
1 stop6h 29m
Delta
Fri 2/203:55 pm
GCM
-
HPN
2 stops20h 01m
Delta
Deal found 1/21$326
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Tue 2/176:49 pm
HPN
-
GCM
2 stops17h 16m
American Airlines
Thu 2/194:25 pm
GCM
-
HPN
2 stops24h 34m
American Airlines
Deal found 1/21$366
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Tue 2/176:00 am
HPN
-
GCM
1 stop8h 35m
American Airlines
Wed 2/253:45 pm
GCM
-
HPN
1 stop7h 42m
American Airlines
Deal found 1/21$373
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Tue 2/176:00 am
HPN
-
GCM
1 stop8h 35m
American Airlines
Tue 2/244:25 pm
GCM
-
HPN
2 stops23h 34m
American Airlines
Deal found 1/21$378
This American Airlines deal was found by Cheapflights users on 1/23. 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.
Wed 5/136:57 pm
HPN
-
GCM
2 stops19h 14m
American Airlines
Sun 5/1712:00 pm
GCM
-
HPN
2 stops20h 29m
American Airlines
Deal found 1/23$388
This American Airlines deal was found by Cheapflights users on 1/22. 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.
Thu 2/126:00 am
HPN
-
GCM
1 stop8h 35m
American Airlines
Tue 2/178:45 am
GCM
-
HPN
1 stop14h 42m
American Airlines
Deal found 1/22$416
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Tue 2/174:30 pm
HPN
-
GCM
1 stop22h 05m
American Airlines
Sun 2/224:25 pm
GCM
-
HPN
2 stops30h 34m
American Airlines
Deal found 1/21$422

Find 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 January 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$306
(American Airlines)

One-way from

$110
(American Airlines)

Popular in

April

Cheapest in

January

Average price

$370
Provider with most accurate pricing for New York (NYC)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-George Town Owen Roberts Intl flights.
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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. 2% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 24, 2026.
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 3/9

6:54 pm-11:05 am

2 stops17h 11m

George Town Owen Roberts Intl

Mon 3/16

2:35 pm-11:29 am

2 stops19h 54m

$306

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 2/18

6:00 am-12:29 pm

1 stop6h 29m

George Town Owen Roberts Intl

Wed 2/25

1:54 pm-10:00 pm

1 stop8h 06m

$321

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 2/18

6:00 am-12:29 pm

1 stop6h 29m

George Town Owen Roberts Intl

Fri 2/20

3:55 pm-11:56 am

2 stops20h 01m

$326

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 2/17

6:00 am-2:35 pm

1 stop8h 35m

George Town Owen Roberts Intl

Thu 2/19

4:25 pm-9:29 am

2 stops17h 04m

$366

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 2/18

6:00 am-2:35 pm

1 stop8h 35m

George Town Owen Roberts Intl

Thu 2/19

4:25 pm-4:59 pm

2 stops24h 34m

$366

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 2/17

4:30 pm-3:25 pm

2 stops22h 55m

George Town Owen Roberts Intl

Tue 2/24

1:05 pm-10:59 pm

2 stops9h 54m

$378

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 2/17

5:30 pm-2:45 pm

2 stops21h 15m

George Town Owen Roberts Intl

Fri 2/20

4:30 pm-11:29 am

2 stops18h 59m

$378

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 2/17

5:29 pm-12:08 pm

2 stops18h 39m

George Town Owen Roberts Intl

Wed 2/25

8:45 am-10:59 pm

2 stops14h 14m

$378

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 4/2

6:30 am-1:44 pm

1 stop8h 14m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

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 January 24, 2026.
See what other customers who have flown with American Airlines 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.
American Airlines
7.2
Good
11,193 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,193 reviews
American Airlines
7.2
Good
11,193 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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.

  • How long is the flight from Westchester County to Cayman Islands?

    There are many flights that can get you from Westchester County to Cayman Islands in 6h 29m. Fly via American Airlines or Delta to get the fastest option. The distance from Westchester County to Cayman Islands is about 1570 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

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 January 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$529FlexibilityNo cancel feeOn-time71%

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