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Cayman Islands

$110+ 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
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/28. 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.
Tue 2/106:00 am
HPN
-
GCM
1 stop6h 40m
Delta
Wed 2/112:05 pm
GCM
-
HPN
1 stop7h 55m
Delta
Deal found 1/28$329
This American Airlines deal was found by Cheapflights users on 1/28. 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 3/196:30 am
HPN
-
GCM
1 stop8h 14m
American Airlines
Mon 3/233:30 pm
GCM
-
HPN
2 stops18h 59m
American Airlines
Deal found 1/28$330
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/166:00 am
HPN
-
GCM
1 stop8h 35m
American Airlines
Tue 2/174:25 pm
GCM
-
HPN
2 stops19h 04m
American Airlines
Deal found 1/27$335
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/37:00 am
HPN
-
GCM
1 stop7h 45m
American Airlines
Fri 2/133:45 pm
GCM
-
HPN
1 stop7h 42m
American Airlines
Deal found 1/28$345
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/107:00 am
HPN
-
GCM
1 stop7h 45m
American Airlines
Wed 2/113:45 pm
GCM
-
HPN
2 stops17h 44m
American Airlines
Deal found 1/28$393
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/166:00 am
HPN
-
GCM
1 stop8h 35m
American Airlines
Fri 2/204:30 pm
GCM
-
HPN
2 stops18h 59m
American Airlines
Deal found 1/28$401
This American Airlines deal was found by Cheapflights users on 1/28. 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 3/267:47 am
HPN
-
GCM
2 stops36h 28m
American Airlines
Mon 3/302:30 pm
GCM
-
HPN
2 stops21h 37m
American Airlines
Deal found 1/28$406

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(Delta)

One-way from

$110
(American Airlines)

Popular in

April

Cheapest in

January

Average price

$369
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 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. 2% potential increase in price ($12 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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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 January 29, 2026.
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 2/10

6:00 am-12:40 pm

1 stop6h 40m

George Town Owen Roberts Intl

Wed 2/11

2:05 pm-10:00 pm

1 stop7h 55m

$329

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 3/19

6:30 am-1:44 pm

1 stop8h 14m

George Town Owen Roberts Intl

Mon 3/23

3:30 pm-11:29 am

2 stops18h 59m

$330

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Mon 2/16

6:00 am-2:35 pm

1 stop8h 35m

George Town Owen Roberts Intl

Tue 2/17

4:25 pm-11:29 am

2 stops19h 04m

$335

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Mon 2/16

6:00 am-2:35 pm

1 stop8h 35m

George Town Owen Roberts Intl

Fri 2/20

4:30 pm-11:29 am

2 stops18h 59m

$401

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Tue 2/17

6:00 am-2:35 pm

1 stop8h 35m

George Town Owen Roberts Intl

Fri 2/20

4:30 pm-11:29 am

2 stops18h 59m

$401

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 3/26

7:47 am-7:15 pm

2 stops36h 28m

George Town Owen Roberts Intl

Mon 3/30

2:30 pm-1:07 pm

2 stops21h 37m

$406

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Fri 3/13

6:30 am-1:44 pm

1 stop8h 14m

George Town Owen Roberts Intl

Fri 3/20

7:45 am-11:29 pm

1 stop14h 44m

$413

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Fri 3/20

7:00 am-1:35 pm

1 stop7h 35m

George Town Owen Roberts Intl

Mon 3/23

2:44 pm-5:07 pm

1 stop25h 23m

$420

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Sat 2/14

5:29 pm-11:50 am

2 stops18h 21m

George Town Owen Roberts Intl

Wed 2/18

8:45 am-11:27 pm

1 stop14h 42m

$428

White PlainsGeorge Town

HPN - GCM

HPNGCM

White Plains Westchester County

Thu 4/2

6:30 am-1:44 pm

1 stop8h 14m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 13 results
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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 $332). 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 January 29, 2026.
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
11,205 reviews

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,205 reviews
American Airlines
7.2
Good
11,205 reviews

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 $329, Delta can have you in Cayman Islands from White Plains in 6h 40m. The distance from White Plains 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 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 $332). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$529FlexibilityNo cancel feeOn-time71%

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