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Cayman Islands

$108+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — GCM
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
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 December 3, 2025.

This American Airlines deal was found by Cheapflights users on 12/2. 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.
Sun 12/145:19 pmHPN - GCM
2 stops18h 40mAmerican Airlines
Thu 12/183:11 pmGCM - HPN
2 stops19h 23mAmerican Airlines
Deal found 12/2$349
This JetBlue deal was found by Cheapflights users on 12/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:00 amHPN - GCM
1 stop6h 55mJetBlue
Sat 12/202:55 pmGCM - HPN
1 stop7h 05mJetBlue
Deal found 12/2$350
This JetBlue deal was found by Cheapflights users on 12/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/137:00 amHPN - GCM
1 stop6h 55mJetBlue
Sat 12/202:55 pmGCM - HPN
1 stop7h 05mJetBlue
Deal found 12/2$360
This American Airlines deal was found by Cheapflights users on 12/2. 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 12/136:49 pmHPN - GCM
2 stops19h 55mAmerican Airlines
Sat 12/203:15 pmGCM - HPN
2 stops19h 19mAmerican Airlines
Deal found 12/2$411
This American Airlines deal was found by Cheapflights users on 12/2. 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.
Sun 12/147:59 amHPN - GCM
1 stop28h 00mAmerican Airlines
Sat 12/203:15 pmGCM - HPN
1 stop7h 45mAmerican Airlines
Deal found 12/2$414
This American Airlines deal was found by Cheapflights users on 12/2. 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 12/136:30 amHPN - GCM
2 stops7h 52mAmerican Airlines
Sun 12/2112:50 pmGCM - HPN
2 stops21h 44mAmerican Airlines
Deal found 12/2$416
This American Airlines deal was found by Cheapflights users on 12/2. 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.
Sun 12/147:59 amHPN - GCM
1 stop28h 00mAmerican Airlines
Sun 12/213:45 pmGCM - HPN
1 stop6h 57mAmerican Airlines
Deal found 12/2$419
This Delta deal was found by Cheapflights users on 11/30. 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.
Thu 12/46:10 amHPN - GCM
1 stop6h 25mDelta
Mon 12/81:50 pmGCM - HPN
1 stop8h 19mDelta
Deal found 11/30$484

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 December 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$270
(American Airlines)

One-way from

$108
(Delta)

Popular in

April

Cheapest in

January

Average price

$573
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 ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 3, 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

Thu 1/22

5:12 pm-2:40 pm

2 stops21h 28m

George Town Owen Roberts Intl

Sat 1/24

3:25 pm-10:00 pm

1 stop6h 35m

$325

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sun 12/14

5:19 pm-11:59 am

2 stops18h 40m

George Town Owen Roberts Intl

Thu 12/18

3:11 pm-10:34 am

2 stops19h 23m

$349

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 12/16

7:00 am-1:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Sat 12/20

2:55 pm-10:00 pm

1 stop7h 05m

$350

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sat 12/13

7:00 am-1:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Sat 12/20

2:55 pm-10:00 pm

1 stop7h 05m

$360

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 1/15

7:00 am-8:20 pm

1 stop13h 20m

George Town Owen Roberts Intl

Thu 1/22

8:50 am-5:00 pm

1 stop8h 10m

$372

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Mon 12/15

6:43 pm-12:10 pm

2 stops17h 27m

George Town Owen Roberts Intl

Sat 12/20

3:15 pm-11:00 pm

1 stop7h 45m

$411

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 12/16

6:43 pm-12:24 pm

2 stops17h 41m

George Town Owen Roberts Intl

Sat 12/20

3:15 pm-10:34 am

2 stops19h 19m

$411

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sun 12/14

5:59 pm-11:59 am

2 stops18h 00m

George Town Owen Roberts Intl

Sat 12/20

3:15 pm-10:34 am

2 stops19h 19m

$411

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sun 4/19

6:00 am-11:24 am

1 stop6h 24m

$108

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 12/11

6:10 am-12:35 pm

1 stop6h 25m

$112

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 16 results
1
2

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 December 3, 2025.
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
11,045 reviews

Crew

8.0

Entertainment

6.9

Food

6.5

Boarding

7.5

Overall

7.2

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.
American Airlines
7.2
Good
11,045 reviews
American Airlines
7.2
Good
11,045 reviews

Crew

8.0

Entertainment

6.9

Food

6.5

Boarding

7.5

Overall

7.2

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.

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 55m. Fly via Delta, American Airlines, or JetBlue 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 December 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$554FlexibilityNo cancel feeOn-time71%

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