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Cayman Islands

$166+ Cheap flights from White Plains (HPN) 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
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Cheap flight deals from White Plains to Cayman Islands

Keep the following information in mind while searching for White Plains to Cayman Islands flight deals. Data was last updated November 5, 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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From White Plains Westchester County to Cayman Islands
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One-way flight from White Plains Westchester County to Cayman Islands
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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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Find flight deals from White Plains to Cayman Islands

Cheapest flights from White Plains to Cayman Islands
Explore the most affordable flight options available from White Plains to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 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 11/4. 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 11/1512:55 pmGCM - HPN
1 stop9h 52mAmerican Airlines
Deal found 11/4$344
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/196:29 amHPN - GCM
1 stop8h 06mAmerican Airlines
Fri 12/263:11 pmGCM - HPN
2 stops19h 23mAmerican Airlines
Deal found 11/3$503
This American Airlines deal was found by Cheapflights users on 11/4. 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 12/294:30 pmHPN - GCM
1 stop22h 05mAmerican Airlines
Thu 1/13:45 pmGCM - HPN
2 stops17h 44mAmerican Airlines
Deal found 11/4$537
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

Cheapflights Fare Finder

 
Customize your flight search to find flights from White Plains 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 November 5, 2025.
Use the filters below to find and compare flights from White Plains to the Cayman Islands that are best for you.

Fly from

White Plains

Fly to

Cayman Islands

Route

Depart

Return

Price

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 1/27

6:40 pm-11:26 am

1 stop16h 46m

George Town Owen Roberts Intl

Sat 1/31

8:45 am-10:59 pm

1 stop14h 14m

$304

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

Tue 2/17

6:55 pm-2:45 pm

2 stops19h 50m

George Town Owen Roberts Intl

Sat 2/21

12:54 pm-9:29 am

2 stops20h 35m

$523

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 4/2

5:04 pm-10:45 am

2 stops18h 41m

$166

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 2/24

6:00 am-12:35 pm

1 stop6h 35m

$268

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 4/2

6:00 am-11:35 am

1 stop6h 35m

$293

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 2/24

5:12 pm-1:44 pm

2 stops44h 32m

$1,312

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Best time to book a flight from White Plains to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from White Plains 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 White Plains to the Cayman Islands

What is the cheapest month to book a flight from White Plains to Cayman Islands?

Currently, October is the cheapest month in which you can book a flight from White Plains to Cayman Islands (average of $119). Flying from White Plains to Cayman Islands in June is currently the most expensive (average of $348). 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.

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 November 5, 2025.
Peruse reviews from past customers who have flown with American Airlines from White Plains to the Cayman Islands to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,042 reviews

Food

6.4

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

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
11,042 reviews
American Airlines
7.2
Good
11,042 reviews

Food

6.4

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

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 White Plains to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from White Plains to Cayman Islands?

    If you book a flight to Cayman Islands from White Plains, you will be flying from Westchester County, which is the city’s only airport. White Plains Westchester County (HPN) is located 3.7 mi from the center of White Plains.

  • How long is the flight from White Plains to Cayman Islands?

    For as low as $304, American Airlines can have you in Cayman Islands from White Plains in 16h 46m. The distance from White Plains to Cayman Islands is about 1570 mi.

  • Can I find deals for flights from White Plains to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on White Plains to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from White Plains to Cayman Islands?

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

  • Can I find deals for business class flights from White Plains to Cayman Islands?

    Yes. Cheapflights offers flight deals from White Plains 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.

  • What is the cheapest month to book a flight from White Plains to Cayman Islands?

    Currently, October is the cheapest month in which you can book a flight from White Plains to Cayman Islands (average of $119). Flying from White Plains to Cayman Islands in June is currently the most expensive (average of $348). 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

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Alternative routes for White Plains to Cayman Islands

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Top airline flying from White Plains to Cayman Islands

Discover the top airline that operate flights from White Plains 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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$529FlexibilityNo cancel feeOn-time71%

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