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Grand Cayman

$166+ Cheap flights from Westchester County to Grand Cayman

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
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Find flight deals from Westchester County to Grand Cayman

Cheapest flights from Westchester County to Grand Cayman
Explore the most affordable flight options available from Westchester County to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2025.

This American Airlines deal was found by Cheapflights users on 11/5. 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.
Sun 12/76:30 amHPN - GCM
2 stops7h 54mAmerican Airlines
Sat 12/131:25 pmGCM - HPN
2 stops20h 04mAmerican Airlines
Deal found 11/5$309
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:10 amHPN - GCM
1 stop7h 50mAmerican Airlines
Sat 11/153:18 pmGCM - HPN
1 stop7h 29mAmerican Airlines
Deal found 11/6$344
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Mon 12/225:16 pmHPN - GCM
2 stops18h 41mAmerican Airlines
Tue 12/301:05 pmGCM - HPN
2 stops20h 24mAmerican Airlines
Deal found 11/5$414
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Mon 12/225:16 pmHPN - GCM
2 stops18h 41mAmerican Airlines
Wed 12/313:35 pmGCM - HPN
1 stop19h 54mAmerican Airlines
Deal found 11/5$422
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:43 pmHPN - GCM
2 stops17h 30mAmerican Airlines
Wed 11/269:00 amGCM - HPN
2 stops14h 29mAmerican Airlines
Deal found 11/6$438
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Mon 12/225:16 pmHPN - GCM
2 stops18h 41mAmerican Airlines
Thu 1/17:30 amGCM - HPN
2 stops36h 57mAmerican Airlines
Deal found 11/5$510
This JetBlue deal was found by Cheapflights users on 11/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:30 amHPN - GCM
1 stop7h 25mJetBlue
Sat 12/272:55 pmGCM - HPN
1 stop7h 05mJetBlue
Deal found 11/5$540
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:27 amHPN - GCM
1 stop8h 08mAmerican Airlines
Thu 1/13:45 pmGCM - HPN
2 stops17h 44mAmerican Airlines
Deal found 11/6$555

Cheap flight deals from Westchester County to Grand Cayman

Keep the following information in mind while searching for Westchester County to Grand Cayman flight deals. Data was last updated November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$304
(American Airlines)

One-way from

$166
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$448
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 Grand Cayman
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One-way flight from Westchester County to Grand Cayman
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Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Grand Cayman 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 November 6, 2025.
Use the filters below to find and compare flights from Westchester County to Grand Cayman that are best for you.

Fly from

Westchester County

Fly to

Grand Cayman

Route

Depart

Return

Price

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sun 12/7

6:30 am-2:24 pm

2 stops7h 54m

George Town Owen Roberts Intl

Sat 12/13

1:25 pm-9:29 am

2 stops20h 04m

$309

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Mon 2/2

7:00 am-8:25 pm

1 stop13h 25m

George Town Owen Roberts Intl

Sat 2/7

3:24 pm-9:29 am

2 stops18h 05m

$309

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 3/17

7:00 am-2:20 pm

1 stop8h 20m

George Town Owen Roberts Intl

Wed 3/18

3:15 pm-10:56 pm

1 stop6h 41m

$384

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 1/1

6:56 pm-12:05 pm

2 stops17h 09m

George Town Owen Roberts Intl

Mon 1/5

3:45 pm-10:30 am

2 stops18h 45m

$402

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Mon 12/22

5:16 pm-11:57 am

2 stops18h 41m

George Town Owen Roberts Intl

Tue 12/30

1:05 pm-9:29 am

2 stops20h 24m

$414

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Mon 12/22

5:16 pm-11:57 am

2 stops18h 41m

George Town Owen Roberts Intl

Wed 12/31

3:35 pm-11:29 am

1 stop19h 54m

$422

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 11/19

1:30 pm-11:57 am

1 stop22h 27m

George Town Owen Roberts Intl

Wed 11/26

9:00 am-11:29 pm

2 stops14h 29m

$486

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sat 12/20

6:30 am-1:55 pm

1 stop7h 25m

George Town Owen Roberts Intl

Sat 12/27

2:55 pm-10:00 pm

1 stop7h 05m

$540

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 4/2

5:04 pm-10:45 am

2 stops18h 41m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

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

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

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated November 6, 2025.
Peruse reviews from past customers who have flown with American Airlines from Westchester County to Grand Cayman to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,040 reviews

Entertainment

6.9

Comfort

7.2

Boarding

7.5

Food

6.4

Crew

8.0

Overall

7.2

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,040 reviews
American Airlines
7.2
Good
11,040 reviews

Entertainment

6.9

Comfort

7.2

Boarding

7.5

Food

6.4

Crew

8.0

Overall

7.2

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Grand Cayman. 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 Grand Cayman?

    Airlines like American Airlines fly from Westchester County to Grand Cayman in about 7h 54m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 1570 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Westchester County to Grand Cayman 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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Top airline flying from Westchester County to Grand Cayman

Discover the top airline that operate flights from Westchester County to Grand Cayman. 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$529FlexibilityNo cancel feeOn-time71%

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