Find a great deal and save up to 24% 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 $327.
Our data shows that September tends to be the cheapest month to fly to Caribbean from New Windsor. Users have commonly found prices around $323 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
$364 - $502
Route
Depart
Return
Price
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 6/15
1 stop14h 28m
San Juan Luis Munoz Marin Intl
Wed 6/19
1 stop13h 13m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 6/8
1 stop14h 28m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop11h 40m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 6/9
1 stop16h 13m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop11h 40m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 6/16
1 stop16h 13m
San Juan Luis Munoz Marin Intl
Wed 6/19
1 stop13h 13m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 6/15
1 stop14h 28m
San Juan Luis Munoz Marin Intl
Sat 6/22
1 stop15h 44m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 6/8
1 stop14h 28m
San Juan Luis Munoz Marin Intl
Sat 6/22
1 stop15h 44m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 6/22
1 stop16h 23m
San Juan Luis Munoz Marin Intl
Sat 6/29
1 stop15h 44m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Wed 7/10
1 stop9h 16m
San Juan Luis Munoz Marin Intl
Wed 7/17
1 stop10h 55m
New Windsor StewartSan Juan Luis Munoz Marin Intl
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 6/8
3 stops34h 42m
San Juan Luis Munoz Marin Intl
Wed 6/12
1 stop11h 40m
No data available for this route at this time. Please check back soon.
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