Find a great deal and save up to 27% 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 $326.
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
$276 - $505
Route
Depart
Return
Price
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Mon 6/3
1 stop15h 21m
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop13h 13m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 6/2
2 stops14h 05m
San Juan Luis Munoz Marin Intl
Thu 6/6
3 stops19h 18m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Fri 5/17
1 stop11h 27m
San Juan Luis Munoz Marin Intl
Sat 5/18
2 stops19h 10m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 6/2
2 stops14h 05m
San Juan Luis Munoz Marin Intl
Thu 6/6
2 stops17h 58m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 6/9
1 stop14h 57m
San Juan Luis Munoz Marin Intl
Sun 6/16
2 stops24h 14m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 5/30
1 stop14h 34m
San Juan Luis Munoz Marin Intl
Sat 6/22
2 stops11h 51m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Wed 6/19
2 stops16h 17m
San Juan Luis Munoz Marin Intl
Sat 6/22
2 stops11h 51m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 5/16
1 stop14h 34m
San Juan Luis Munoz Marin Intl
Sat 5/18
1 stop16h 01m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 6/9
2 stops21h 36m
San Juan Luis Munoz Marin Intl
Sun 6/16
2 stops24h 14m
No data available for this route at this time. Please check back soon.
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