$110+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — GCM
Apr 3 — Apr 101
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Westchester County to Grand Cayman with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Westchester County to Grand Cayman
Cheapest
Best
Last-minute
One-way
Cheapest flights from Westchester County to Grand CaymanExplore 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 March 4, 2026.
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 March 4, 2026.
This Priceline deal was found by Cheapflights users on 2/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:00 am
HPN
- GCM
1 stop5h 39m
JetBlue
Tue 4/211:55 pm
GCM
- HPN
1 stop7h 41m
JetBlue
Deal found 2/28![JetBlue logo]()
$307
This American Airlines deal was found by Cheapflights users on 2/28. 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 4/146:57 pm
HPN
- GCM
2 stops19h 13m
American Airlines
Tue 4/2112:00 pm
GCM
- HPN
2 stops20h 29m
American Airlines
Deal found 2/28![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 3/1. 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 7/310:00 am
HPN
- GCM
1 stop26h 20m
American Airlines
Sat 7/112:55 pm
GCM
- HPN
2 stops19h 34m
American Airlines
Deal found 3/1![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 2/28. 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.
Fri 3/205:30 pm
HPN
- GCM
2 stops17h 53m
American Airlines
Mon 3/232:35 pm
GCM
- HPN
2 stops19h 54m
American Airlines
Deal found 2/28![American Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Mon 11/27:59 am
HPN
- GCM
1 stop7h 21m
American Airlines
Sat 11/71:00 pm
GCM
- HPN
2 stops20h 29m
American Airlines
Deal found 3/3![American Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 3/1. 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 3/266:54 pm
HPN
- GCM
1 stop17h 16m
American Airlines
Tue 3/317:45 am
GCM
- HPN
1 stop14h 44m
American Airlines
Deal found 3/1![American Airlines logo]()
$381
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Mon 11/27:59 am
HPN
- GCM
1 stop7h 21m
American Airlines
Fri 11/64:10 pm
GCM
- HPN
1 stop6h 37m
American Airlines
Deal found 3/3![American Airlines logo]()
$405
Best flights from Westchester County to Grand CaymanDiscover carefully curated flight deals from Westchester County to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 4, 2026.
Discover carefully curated flight deals from Westchester County to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 4, 2026.
This American Airlines deal was found by Cheapflights users on 2/28. 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 4/146:57 pm
HPN
- GCM
2 stops19h 13m
American Airlines
Tue 4/2112:00 pm
GCM
- HPN
2 stops20h 29m
American Airlines
Deal found 2/28![American Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 2/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:00 am
HPN
- GCM
1 stop8h 05m
Delta
Wed 3/181:12 pm
GCM
- HPN
1 stop7h 55m
Delta
Deal found 2/27![Delta logo]()
$641
This American Airlines deal was found by Cheapflights users on 3/1. 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 7/36:56 pm
HPN
- GCM
2 stops19h 14m
American Airlines
Sat 7/112:55 pm
GCM
- HPN
2 stops19h 34m
American Airlines
Deal found 3/1![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 2/28. 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.
Fri 3/205:30 pm
HPN
- GCM
2 stops17h 53m
American Airlines
Mon 3/232:35 pm
GCM
- HPN
2 stops19h 54m
American Airlines
Deal found 2/28![American Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 3/1. 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 7/41:42 pm
HPN
- GCM
1 stop22h 38m
American Airlines
Sat 7/112:55 pm
GCM
- HPN
2 stops19h 34m
American Airlines
Deal found 3/1![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Wed 6/106:59 pm
HPN
- GCM
2 stops17h 02m
American Airlines
Mon 6/1512:33 pm
GCM
- HPN
1 stop6h 56m
American Airlines
Deal found 3/3![American Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 2/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:00 am
HPN
- GCM
1 stop6h 47m
Delta
Thu 3/191:12 pm
GCM
- HPN
1 stop7h 55m
Delta
Deal found 2/27![Delta logo]()
$741
This American Airlines deal was found by Cheapflights users on 2/27. 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.
Sun 3/296:54 pm
HPN
- GCM
1 stop16h 46m
American Airlines
Sat 4/411:55 am
GCM
- HPN
1 stop20h 34m
American Airlines
Deal found 2/27![American Airlines logo]()
$628
Last-minute flights from Westchester County to Grand CaymanDiscover last-minute flight deals from Westchester County to Grand Cayman. Data last updated March 4, 2026 and is based on user searches.
Discover last-minute flight deals from Westchester County to Grand Cayman. Data last updated March 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/28. 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.
Fri 3/205:30 pm
HPN
- GCM
2 stops17h 53m
American Airlines
Mon 3/232:35 pm
GCM
- HPN
2 stops19h 54m
American Airlines
Deal found 2/28![American Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 3/1. 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 3/266:54 pm
HPN
- GCM
1 stop17h 16m
American Airlines
Tue 3/317:45 am
GCM
- HPN
1 stop14h 44m
American Airlines
Deal found 3/1![American Airlines logo]()
$381
This Priceline deal was found by Cheapflights users on 2/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:00 am
HPN
- GCM
1 stop5h 39m
JetBlue
Tue 4/211:55 pm
GCM
- HPN
1 stop7h 41m
JetBlue
Deal found 2/28![JetBlue logo]()
$307
This American Airlines deal was found by Cheapflights users on 2/28. 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 4/146:57 pm
HPN
- GCM
2 stops19h 13m
American Airlines
Tue 4/2112:00 pm
GCM
- HPN
2 stops20h 29m
American Airlines
Deal found 2/28![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 2/27. 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.
Thu 4/306:59 pm
HPN
- GCM
2 stops19h 11m
American Airlines
Sun 5/312:00 pm
GCM
- HPN
2 stops20h 29m
American Airlines
Deal found 2/27![American Airlines logo]()
$560
One-way flights from Westchester County to Grand CaymanSearch for one-way flight options from Westchester County to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated March 4, 2026.
Search for one-way flight options from Westchester County to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated March 4, 2026.
This American Airlines deal was found by Cheapflights users on 2/28. 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 4/26:30 am
HPN
- GCM
1 stop8h 14m
American Airlines
Deal found 2/28![American Airlines logo]()
$110
This American Airlines deal was found by Cheapflights users on 3/1. 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 3/315:29 pm
HPN
- GCM
2 stops18h 11m
American Airlines
Deal found 3/1![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 3/1. 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 4/16:30 am
HPN
- GCM
2 stops13h 45m
American Airlines
Deal found 3/1![American Airlines logo]()
$158
This Delta deal was found by Cheapflights users on 3/1. 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.
Mon 3/236:00 am
HPN
- GCM
1 stop6h 47m
Delta
Deal found 3/1![Delta logo]()
$268
This KAYAK deal was found by Cheapflights users on 3/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:59 am
HPN
- GCM
1 stop6h 46m
JetBlue
Deal found 3/3![JetBlue logo]()
$274
This American Airlines deal was found by Cheapflights users on 2/28. 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.
Fri 4/35:30 pm
HPN
- GCM
2 stops18h 30m
American Airlines
Deal found 2/28![American Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 2/28. 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.
Sat 3/286:00 am
HPN
- GCM
1 stop6h 47m
Delta
Deal found 2/28![Delta logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/319:23 am
HPN
- GCM
3 stops31h 42m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$342
Find 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 March 4, 2026.
Round-trip from | $307 (Priceline) |
|---|---|
One-way from | $110 (American Airlines) |
Popular in | July |
Cheapest in | January |
Average price | $389 |
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 March 4, 2026.
Use the filters below to find and compare flights from Westchester County to Grand Cayman that are best for you.
Fly from
Fly to
Route
Depart
Return
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Tue 4/14
6:57 pm-1:10 pm
2 stops19h 13m
George Town Owen Roberts Intl
Tue 4/21
12:00 pm-9:29 am
2 stops20h 29m
$330
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Fri 7/3
6:56 pm-1:10 pm
2 stops19h 14m
George Town Owen Roberts Intl
Sat 7/11
2:55 pm-11:29 am
2 stops19h 34m
$330
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Fri 3/20
5:30 pm-10:23 am
2 stops17h 53m
George Town Owen Roberts Intl
Mon 3/23
2:35 pm-11:29 am
2 stops19h 54m
$340
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Sat 7/4
1:42 pm-11:20 am
1 stop22h 38m
George Town Owen Roberts Intl
Sat 7/11
2:55 pm-11:29 am
2 stops19h 34m
$429
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Wed 6/10
6:59 pm-11:01 am
2 stops17h 02m
George Town Owen Roberts Intl
Mon 6/15
12:33 pm-8:29 pm
1 stop6h 56m
$484
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Sun 3/29
6:54 pm-10:40 am
1 stop16h 46m
George Town Owen Roberts Intl
Sat 4/4
11:55 am-9:29 am
1 stop20h 34m
$628
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Sat 3/14
6:00 am-1:05 pm
1 stop8h 05m
George Town Owen Roberts Intl
Wed 3/18
1:12 pm-10:07 pm
1 stop7h 55m
$641
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Mon 3/16
6:00 am-11:47 am
1 stop6h 47m
George Town Owen Roberts Intl
Thu 3/19
1:12 pm-10:07 pm
1 stop7h 55m
$741
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Thu 4/2
6:30 am-1:44 pm
1 stop8h 14m
$110
White PlainsGeorge Town
HPN - GCM
HPNGCM
White Plains Westchester County
Fri 4/3
6:30 am-1:44 pm
1 stop8h 14m
$110
Showing 1-10 of 13 resultsSorted by cheapest first
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.
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 Grand Cayman
zzREU-zzLAW
HPN-GCM
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 March 4, 2026.
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.
Boarding
7.5
Entertainment
6.9
Food
6.4
Crew
8.0
Comfort
7.2
Overall
7.1
Reviews
1 / 20
2.0
MediocreSusie,Jan 2026
CLT - TPA
Boarding
7.5
Entertainment
6.9
Food
6.4
Crew
8.0
Comfort
7.2
Overall
7.1
Reviews
1 / 20
2.0
MediocreSusie,Jan 2026
CLT - TPA
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.
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Westchester County to Grand Cayman
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Westchester County to Grand Cayman by cabin class
Find flights from Westchester County to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Westchester County and Grand Cayman flights
Browse other Westchester County and Grand Cayman flight options. Last updated on March 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 March 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$354 | Average$513 | FlexibilityNo cancel fee | On-time71% |