Find a great deal and save up to 26% by booking at least 31 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from New Windsor to Caribbean within the next two weeks, with the cheapest ticket starting at $323.
Our data shows that September tends to be the cheapest month to fly to Caribbean from New Windsor. Users have commonly found prices around $324 for the month, but tickets can be as low as $85. Due to multiple factors, prepare for potentially higher prices in December.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Windsor to Caribbean as you normally would.
Fly from
Fly to
Budget
$357 - $473
Route
Depart
Return
Price
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 6/6
1 stop14h 47m
San Juan Luis Munoz Marin Intl
Thu 6/13
3 stops30h 26m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 6/6
2 stops16h 45m
San Juan Luis Munoz Marin Intl
Thu 6/13
3 stops30h 26m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 6/6
1 stop14h 47m
San Juan Luis Munoz Marin Intl
Thu 6/13
2 stops24h 14m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 6/13
1 stop16h 08m
San Juan Luis Munoz Marin Intl
Thu 6/20
2 stops11h 47m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 6/13
1 stop14h 47m
San Juan Luis Munoz Marin Intl
Thu 6/20
3 stops30h 26m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 7/6
1 stop16h 21m
San Juan Luis Munoz Marin Intl
Wed 7/10
1 stop10h 55m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 7/6
1 stop16h 21m
San Juan Luis Munoz Marin Intl
Wed 7/10
1 stop7h 23m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 6/13
1 stop14h 47m
San Juan Luis Munoz Marin Intl
Wed 6/19
2 stops13h 54m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Wed 7/10
1 stop14h 24m
San Juan Luis Munoz Marin Intl
Sat 7/20
1 stop14h 05m
No data available for this route at this time. Please check back soon.
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