$345+ Cheap flights from Westchester County to the Cayman Islands
This is the cheapest round-trip 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
May 10 — May 171
Round-trip
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 April 10, 2026.
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 April 10, 2026.
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:17 pm
HPN
- GCM
1 stop17h 43m
Delta
Wed 4/151:25 pm
GCM
- HPN
1 stop7h 38m
Delta
Deal found 4/10![Delta logo]()
$345
This American Airlines deal was found by Cheapflights users on 4/9. 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.
Sun 11/16:49 pm
HPN
- GCM
2 stops19h 28m
American Airlines
Fri 11/64:10 pm
GCM
- HPN
1 stop17h 19m
American Airlines
Deal found 4/9![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/7. 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 4/196:59 pm
HPN
- GCM
2 stops17h 01m
American Airlines
Wed 4/2212:00 pm
GCM
- HPN
2 stops20h 29m
American Airlines
Deal found 4/7![American Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:29 pm
HPN
- GCM
2 stops18h 32m
American Airlines
Mon 6/112:01 pm
GCM
- HPN
2 stops10h 25m
American Airlines
Deal found 4/10![American Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 4/6. 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 8/226:59 pm
HPN
- GCM
1 stop17h 26m
American Airlines
Sat 8/292:10 pm
GCM
- HPN
2 stops18h 19m
American Airlines
Deal found 4/6![American Airlines logo]()
$407
This JetBlue deal was found by Cheapflights users on 4/6. 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 5/218:29 am
HPN
- GCM
1 stop5h 16m
JetBlue
Thu 5/282:05 pm
GCM
- HPN
1 stop7h 28m
JetBlue
Deal found 4/6![JetBlue logo]()
$411
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:00 am
HPN
- GCM
1 stop6h 00m
American Airlines
Thu 4/162:10 pm
GCM
- HPN
1 stop7h 42m
American Airlines
Deal found 4/10![American Airlines logo]()
$435
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:59 pm
HPN
- GCM
2 stops16h 56m
American Airlines
Sat 4/182:10 pm
GCM
- HPN
2 stops18h 19m
American Airlines
Deal found 4/10![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:59 pm
HPN
- GCM
1 stop17h 32m
American Airlines
Sat 4/182:10 pm
GCM
- HPN
2 stops18h 19m
American Airlines
Deal found 4/10![American Airlines logo]()
$448
Best flights from Westchester County to Cayman IslandsDiscover carefully curated flight deals from Westchester County to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 10, 2026.
Discover carefully curated flight deals from Westchester County to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 10, 2026.
This American Airlines deal was found by Cheapflights users on 4/6. 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 8/226:59 pm
HPN
- GCM
2 stops19h 11m
American Airlines
Sat 8/292:10 pm
GCM
- HPN
2 stops20h 18m
American Airlines
Deal found 4/6![American Airlines logo]()
$350
This JetBlue deal was found by Cheapflights users on 4/6. 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 5/218:29 am
HPN
- GCM
1 stop5h 16m
JetBlue
Thu 5/282:05 pm
GCM
- HPN
1 stop7h 28m
JetBlue
Deal found 4/6![JetBlue logo]()
$411
This Delta deal was found by Cheapflights users on 4/6. 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.
Thu 4/236:00 am
HPN
- GCM
1 stop7h 00m
Delta
Fri 5/11:25 pm
GCM
- HPN
1 stop7h 38m
Delta
Deal found 4/6![Delta logo]()
$494
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:55 am
HPN
- GCM
1 stop28h 35m
American Airlines
Mon 6/112:33 pm
GCM
- HPN
1 stop6h 56m
American Airlines
Deal found 4/10![American Airlines logo]()
$532
This KAYAK deal was found by Cheapflights users on 4/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:05 am
HPN
- GCM
1 stop5h 34m
JetBlue
Thu 4/302:05 pm
GCM
- HPN
1 stop7h 31m
JetBlue
Deal found 4/6![JetBlue logo]()
$584
This American Airlines deal was found by Cheapflights users on 4/9. 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 5/217:55 am
HPN
- GCM
2 stops28h 06m
American Airlines
Tue 5/262:42 pm
GCM
- HPN
2 stops19h 47m
American Airlines
Deal found 4/9![American Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 4/6. 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.
Thu 4/236:00 am
HPN
- GCM
1 stop7h 00m
Delta
Sat 5/21:25 pm
GCM
- HPN
1 stop7h 38m
Delta
Deal found 4/6![Delta logo]()
$641
This American Airlines deal was found by Cheapflights users on 4/9. 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 5/223:22 pm
HPN
- GCM
2 stops20h 33m
American Airlines
Wed 5/275:12 pm
GCM
- HPN
2 stops15h 16m
American Airlines
Deal found 4/9![American Airlines logo]()
$590
This American Airlines deal was found by Cheapflights users on 4/9. 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 5/225:29 pm
HPN
- GCM
2 stops18h 59m
American Airlines
Tue 5/262:42 pm
GCM
- HPN
2 stops24h 17m
American Airlines
Deal found 4/9![American Airlines logo]()
$590
This American Airlines deal was found by Cheapflights users on 4/6. 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 5/215:59 pm
HPN
- GCM
2 stops18h 02m
American Airlines
Thu 5/2812:33 pm
GCM
- HPN
1 stop6h 56m
American Airlines
Deal found 4/6![American Airlines logo]()
$646
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:00 am
HPN
- GCM
1 stop6h 54m
Delta
Wed 5/271:19 pm
GCM
- HPN
1 stop8h 01m
Delta
Deal found 4/9![Delta logo]()
$871
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/215:59 pm
HPN
- GCM
2 stops18h 02m
American Airlines
Mon 5/252:42 pm
GCM
- HPN
2 stops19h 47m
American Airlines
Deal found 4/10![American Airlines logo]()
$691
Last-minute flights from Westchester County to Cayman IslandsDiscover last-minute flight deals from Westchester County to Cayman Islands. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Westchester County to Cayman Islands. Data last updated April 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:17 pm
HPN
- GCM
1 stop17h 43m
Delta
Wed 4/151:25 pm
GCM
- HPN
1 stop7h 38m
Delta
Deal found 4/10![Delta logo]()
$345
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:59 pm
HPN
- GCM
2 stops16h 56m
American Airlines
Sat 4/182:10 pm
GCM
- HPN
2 stops18h 19m
American Airlines
Deal found 4/10![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:59 pm
HPN
- GCM
1 stop17h 32m
American Airlines
Sat 4/182:10 pm
GCM
- HPN
2 stops18h 19m
American Airlines
Deal found 4/10![American Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:00 am
HPN
- GCM
1 stop6h 00m
American Airlines
Thu 4/162:10 pm
GCM
- HPN
1 stop7h 42m
American Airlines
Deal found 4/10![American Airlines logo]()
$435
This American Airlines deal was found by Cheapflights users on 4/7. 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 4/196:59 pm
HPN
- GCM
2 stops17h 01m
American Airlines
Wed 4/2212:00 pm
GCM
- HPN
2 stops20h 29m
American Airlines
Deal found 4/7![American Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 4/6. 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.
Thu 4/236:00 am
HPN
- GCM
1 stop7h 00m
Delta
Fri 5/11:25 pm
GCM
- HPN
1 stop7h 38m
Delta
Deal found 4/6![Delta logo]()
$494
This JetBlue deal was found by Cheapflights users on 4/6. 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 5/218:29 am
HPN
- GCM
1 stop5h 16m
JetBlue
Thu 5/282:05 pm
GCM
- HPN
1 stop7h 28m
JetBlue
Deal found 4/6![JetBlue logo]()
$411
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:29 pm
HPN
- GCM
2 stops18h 32m
American Airlines
Mon 6/112:01 pm
GCM
- HPN
2 stops10h 25m
American Airlines
Deal found 4/10![American Airlines logo]()
$404
One-way flights from Westchester County to Cayman IslandsSearch for one-way flight options from Westchester County to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
Search for one-way flight options from Westchester County to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
HPN
- GCM
1 stop7h 00m
Delta
Deal found 4/10![Delta logo]()
$489
This Delta deal was found by Cheapflights users on 4/7. 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.
Sun 6/286:29 am
HPN
- GCM
1 stop6h 05m
Delta
Deal found 4/7![Delta logo]()
$625
This WestJet deal was found by Cheapflights users on 4/5. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
HPN
- GCM
2 stops31h 44m
WestJet
Deal found 4/5![WestJet logo]()
$1,341
This WestJet deal was found by Cheapflights users on 4/7. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/285:10 pm
HPN
- GCM
2 stops44h 35m
WestJet
Deal found 4/7![WestJet logo]()
$1,358
Find 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 April 10, 2026.
Round-trip from | $350 (American Airlines) |
|---|---|
Popular in | February |
Cheapest in | January |
Average price | $474 |
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 April 10, 2026.
Use the filters below to find and compare flights from Westchester County to the Cayman Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Sat 8/22
6:59 pm-1:10 pm
2 stops19h 11m
George Town Owen Roberts Intl
Sat 8/29
2:10 pm-11:28 am
2 stops20h 18m
$350
Quickest round-trip
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Thu 5/21
8:29 am-12:45 pm
1 stop5h 16m
George Town Owen Roberts Intl
Thu 5/28
2:05 pm-10:33 pm
1 stop7h 28m
$411
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Thu 4/23
6:00 am-12:00 pm
1 stop7h 00m
George Town Owen Roberts Intl
Fri 5/1
1:25 pm-10:03 pm
1 stop7h 38m
$494
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Mon 5/25
7:55 am-11:30 am
1 stop28h 35m
George Town Owen Roberts Intl
Mon 6/1
12:33 pm-8:29 pm
1 stop6h 56m
$532
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Thu 5/21
7:55 am-11:01 am
2 stops28h 06m
George Town Owen Roberts Intl
Tue 5/26
2:42 pm-11:29 am
2 stops19h 47m
$539
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Thu 4/23
8:05 am-12:39 pm
1 stop5h 34m
George Town Owen Roberts Intl
Thu 4/30
2:05 pm-10:36 pm
1 stop7h 31m
$584
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Fri 5/22
3:22 pm-10:55 am
2 stops20h 33m
George Town Owen Roberts Intl
Wed 5/27
5:12 pm-9:28 am
2 stops15h 16m
$590
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Fri 5/22
5:29 pm-11:28 am
2 stops18h 59m
George Town Owen Roberts Intl
Tue 5/26
2:42 pm-3:59 pm
2 stops24h 17m
$590
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Thu 4/23
6:00 am-12:00 pm
1 stop7h 00m
George Town Owen Roberts Intl
Sat 5/2
1:25 pm-10:03 pm
1 stop7h 38m
$641
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Thu 5/21
5:59 pm-11:01 am
2 stops18h 02m
George Town Owen Roberts Intl
Thu 5/28
12:33 pm-8:29 pm
1 stop6h 56m
$646
Showing 1-10 of 16 resultsSorted by cheapest first
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.
HPN-GCM
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
zzREU-KY0
HPN-GCM
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 April 10, 2026.
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.
Comfort
7.2
Crew
7.9
Boarding
7.5
Overall
7.1
Entertainment
6.8
Food
6.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Comfort
7.2
Crew
7.9
Boarding
7.5
Overall
7.1
Entertainment
6.8
Food
6.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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.
Complete your trip
Complete your trip to Cayman Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Westchester County to Cayman Islands by cabin class
Find flights from Westchester County to Cayman Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Westchester County and Cayman Islands flights
Browse other Westchester County and Cayman Islands flight options. Last updated on April 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Cayman Islands regions
Consider these flights traveling to Cayman Islands regions.
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 April 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$354 | Average$513 | FlexibilityNo cancel fee | On-time71% |