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Grand Cayman

$120+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — GCM
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
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 September 19, 2025.

Round-trip from

$348
(American Airlines)

One-way from

$120
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$389
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. 7% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 19, 2025.

This American Airlines deal was found by Cheapflights users on 9/16. 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 11/153:36 pmGCM - HPN
2 stops17h 53mAmerican Airlines
Deal found 9/16$348
This American Airlines deal was found by Cheapflights users on 9/16. 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 11/67:59 amHPN - GCM
1 stop6h 15mAmerican Airlines
Sun 11/91:20 pmGCM - HPN
2 stops20h 09mAmerican Airlines
Deal found 9/16$353
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/206:59 pmHPN - GCM
1 stop17h 21mAmerican Airlines
Sat 10/2512:10 pmGCM - HPN
2 stops20h 19mAmerican Airlines
Deal found 9/18$356
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/216:55 pmHPN - GCM
1 stop17h 25mAmerican Airlines
Sun 10/2612:10 pmGCM - HPN
2 stops21h 24mAmerican Airlines
Deal found 9/18$361
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/215:29 pmHPN - GCM
2 stops18h 41mAmerican Airlines
Sat 10/253:15 pmGCM - HPN
2 stops18h 19mAmerican Airlines
Deal found 9/18$410
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/287:59 amHPN - GCM
1 stop28h 26mAmerican Airlines
Sun 10/512:10 pmGCM - HPN
2 stops21h 24mAmerican Airlines
Deal found 9/15$415
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/217:59 amHPN - GCM
1 stop28h 26mAmerican Airlines
Sun 9/2812:28 pmGCM - HPN
2 stops19h 54mAmerican Airlines
Deal found 9/15$416

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 September 19, 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

Thu 1/8

7:30 am-2:55 pm

1 stop7h 25m

George Town Owen Roberts Intl

Thu 1/15

3:55 pm-10:58 pm

1 stop7h 03m

$328

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sat 11/8

7:10 am-3:00 pm

1 stop7h 50m

George Town Owen Roberts Intl

Sat 11/15

3:36 pm-9:29 am

2 stops17h 53m

$348

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sat 1/3

5:56 pm-11:57 am

2 stops18h 01m

George Town Owen Roberts Intl

Sat 2/7

4:15 pm-10:49 pm

1 stop6h 34m

$348

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Mon 10/20

5:29 pm-11:10 am

2 stops18h 41m

George Town Owen Roberts Intl

Sat 10/25

12:10 pm-9:29 am

2 stops20h 19m

$348

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 10/22

6:55 pm-11:25 am

1 stop17h 30m

George Town Owen Roberts Intl

Sun 10/26

12:10 pm-10:34 am

2 stops21h 24m

$361

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 12/10

5:19 pm-12:00 pm

2 stops18h 41m

$120

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Wed 12/10

7:00 pm-2:55 pm

1 stop19h 55m

$123

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 12/9

6:43 pm-12:01 pm

1 stop17h 18m

$187

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 12/2

5:59 pm-12:03 pm

2 stops18h 04m

$669

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

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 September 19, 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
10,000 reviews

Boarding

7.5

Entertainment

6.9

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Entertainment

6.9

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 7h 25m. The time it takes to get you to your destination can typically vary by up to 25m. 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.

  • What is the cheapest month to book a flight from Westchester County to Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Westchester County to Grand Cayman (average of $467). Flying from Westchester County to Grand Cayman 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

Browse thousands of different options on Cheapflights for your next trip

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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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$554FlexibilityNo cancel feeOn-time71%

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