$116+ Cheap flights from Westchester County 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
Nov 13 — Nov 201
1 adult, Economy
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Cheapest flights from Westchester County to Cayman IslandsExplore the most affordable flight options available from Westchester County to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.
Explore the most affordable flight options available from Westchester County to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/86:00 amHPN - GCM
1 stop9h 00mAmerican Airlines
Sat 11/1512:55 pmGCM - HPN
1 stop9h 52mAmerican Airlines
Deal found 10/12![American Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 10/12. 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 10/305:57 pmHPN - GCM
2 stops18h 13mAmerican Airlines
Mon 11/31:20 pmGCM - HPN
2 stops21h 37mAmerican Airlines
Deal found 10/12![American Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 10/14. 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 11/2712:00 pmHPN - GCM
2 stops26h 14mAmerican Airlines
Mon 12/11:25 pmGCM - HPN
2 stops23h 35mAmerican Airlines
Deal found 10/14![American Airlines logo]()
$443
This American Airlines deal was found by Cheapflights users on 10/14. 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 11/265:21 pmHPN - GCM
2 stops27h 07mAmerican Airlines
Mon 12/19:00 amGCM - HPN
2 stops25h 57mAmerican Airlines
Deal found 10/14![American Airlines logo]()
$479
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/266:30 amHPN - GCM
2 stops13h 58mAmerican Airlines
Wed 12/33:45 pmGCM - HPN
2 stops17h 44mAmerican Airlines
Deal found 10/12![American Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/296:30 amHPN - GCM
2 stops7h 58mAmerican Airlines
Sat 12/63:45 pmGCM - HPN
2 stops19h 07mAmerican Airlines
Deal found 10/12![American Airlines logo]()
$638
Cheap flight deals from Westchester County to Cayman Islands
Keep the following information in mind while searching for Westchester County to Cayman Islands flight deals. Data was last updated October 14, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (American Airlines) |
One-way from | $116 (American Airlines) |
Popular in | December |
Cheapest in | March |
Average price | $396 |
Cheapflights Fare Finder
Customize your flight search to find flights from Westchester County 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 October 14, 2025.
Use the filters below to find and compare flights from Westchester County to the Cayman Islands that are best for you.
Fly from
Westchester County
Fly to
Cayman Islands
Route
Depart
Return
Price
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Sat 11/8
6:00 am-3:00 pm
1 stop9h 00m
George Town Owen Roberts Intl
Sat 11/15
12:55 pm-10:47 pm
1 stop9h 52m
$304
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
Fri 4/3
5:04 pm-6:51 pm
2 stops26h 47m
George Town Owen Roberts Intl
Mon 4/13
1:15 pm-10:42 am
2 stops20h 27m
$389
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Mon 4/6
8:18 am-1:20 pm
1 stop6h 02m
George Town Owen Roberts Intl
Mon 4/13
1:15 pm-10:42 am
2 stops20h 27m
$389
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Thu 4/2
5:04 pm-10:45 am
2 stops18h 41m
$116
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Wed 11/12
6:00 am-12:35 pm
1 stop6h 35m
$190
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Wed 11/12
12:45 pm-1:44 pm
2 stops24h 59m
$1,285
Best time to book a flight from Westchester County to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands 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 the Cayman Islands
No data available for this route at this time. Please check back soon.
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 October 14, 2025.
See what other customers who have flown with American Airlines from Westchester County to the Cayman Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.0
Comfort
7.2
Entertainment
6.9
Overall
7.2
Boarding
7.5
Food
6.4
Reviews
1 / 20
2.0
MediocreJeremy,Sep 2025
SAN - PHL
Crew
8.0
Comfort
7.2
Entertainment
6.9
Overall
7.2
Boarding
7.5
Food
6.4
Reviews
1 / 20
2.0
MediocreJeremy,Sep 2025
SAN - PHL
Related info for your journey
Find useful and relevant information for your journey from Westchester County to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Westchester County to Cayman Islands
See prices for flight routes from nearby airports that may be better suited for you.
Top airline flying from Westchester County to Cayman Islands
Discover the top airline that operate flights from Westchester County 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 October 14, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$356 | Average$529 | FlexibilityNo cancel fee | On-time71% |