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Grand Cayman

$108+ 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — GCM
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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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 January 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$297
(JetBlue)

One-way from

$108
(Delta)

Popular in

April

Cheapest in

January

Average price

$372
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 ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% 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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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 January 12, 2026.

This JetBlue deal was found by Cheapflights users on 1/10. 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.
Thu 5/148:05 amHPN - GCM
1 stop5h 40mJetBlue
Tue 5/192:05 pmGCM - HPN
1 stop7h 31mJetBlue
Deal found 1/10$297
This American Airlines deal was found by Cheapflights users on 1/9. 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 2/257:00 amHPN - GCM
1 stop13h 15mAmerican Airlines
Fri 2/273:45 pmGCM - HPN
1 stop7h 42mAmerican Airlines
Deal found 1/9$325
This American Airlines deal was found by Cheapflights users on 1/9. 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 1/156:40 pmHPN - GCM
2 stops20h 05mAmerican Airlines
Wed 1/218:50 amGCM - HPN
2 stops13h 05mAmerican Airlines
Deal found 1/9$375
This American Airlines deal was found by Cheapflights users on 1/9. 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 3/147:00 amHPN - GCM
1 stop13h 15mAmerican Airlines
Tue 3/1712:05 pmGCM - HPN
1 stop10h 24mAmerican Airlines
Deal found 1/9$384
This American Airlines deal was found by Cheapflights users on 1/9. 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.
Fri 10/27:45 pmHPN - GCM
2 stops16h 05mAmerican Airlines
Tue 10/69:25 amGCM - HPN
2 stops12h 54mAmerican Airlines
Deal found 1/9$390
This American Airlines deal was found by Cheapflights users on 1/9. 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 1/207:00 amHPN - GCM
1 stop7h 45mAmerican Airlines
Thu 1/228:50 amGCM - HPN
1 stop14h 09mAmerican Airlines
Deal found 1/9$407
This American Airlines deal was found by Cheapflights users on 1/9. 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.
Fri 1/166:40 pmHPN - GCM
1 stop16h 46mAmerican Airlines
Thu 1/228:50 amGCM - HPN
1 stop8h 10mAmerican Airlines
Deal found 1/9$432

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 January 12, 2026.
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

Thu 5/14

8:05 am-12:45 pm

1 stop5h 40m

George Town Owen Roberts Intl

Tue 5/19

2:05 pm-10:36 pm

1 stop7h 31m

$297

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 2/25

7:00 am-8:15 pm

1 stop13h 15m

George Town Owen Roberts Intl

Fri 2/27

12:55 pm-9:29 am

2 stops20h 34m

$330

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sun 5/3

6:57 pm-1:11 pm

2 stops19h 14m

George Town Owen Roberts Intl

Sat 5/9

2:10 pm-9:29 am

2 stops18h 19m

$330

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sat 3/14

7:00 am-7:15 pm

1 stop13h 15m

George Town Owen Roberts Intl

Tue 3/17

12:05 pm-11:29 pm

1 stop10h 24m

$384

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 1/21

6:00 am-2:35 pm

1 stop8h 35m

George Town Owen Roberts Intl

Thu 1/22

3:45 pm-10:59 pm

1 stop7h 14m

$407

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 3/10

6:00 am-11:47 am

1 stop6h 47m

George Town Owen Roberts Intl

Sat 3/14

2:30 pm-10:07 pm

1 stop6h 37m

$481

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 3/11

6:00 am-11:47 am

1 stop6h 47m

George Town Owen Roberts Intl

Sat 3/14

2:30 pm-10:07 pm

1 stop6h 37m

$481

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sun 4/19

6:00 am-11:24 am

1 stop6h 24m

George Town Owen Roberts Intl

Thu 4/23

12:45 pm-10:08 pm

1 stop8h 23m

$481

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 3/4

6:00 am-12:29 pm

1 stop6h 29m

George Town Owen Roberts Intl

Sun 3/8

1:12 pm-10:07 pm

1 stop7h 55m

$481

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sun 3/29

5:30 pm-10:40 am

2 stops18h 10m

George Town Owen Roberts Intl

Sat 4/4

3:30 pm-9:29 am

2 stops16h 59m

$481

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/9

Showing 1-10 of 19 results
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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 January 12, 2026.
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
11,111 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,111 reviews
American Airlines
7.2
Good
11,111 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 JetBlue and American Airlines fly from Westchester County to Grand Cayman in about 5h 40m. The time it takes to get you to your destination can typically vary by up to 7h 35m. Airlines will cover a distance of 1570 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$529FlexibilityNo cancel feeOn-time71%

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