Fly from
Fly to
Route
Depart
Return
Price
San JuanNew Windsor
SJU - SWF
SJUSWF
San Juan Luis Munoz Marin Intl
Thu 2/6
10:09 pm-1:20 pm
1 stop16h 11m
New Windsor Stewart
Sun 2/9
7:54 pm-11:18 am
1 stop14h 24m
Santo DomingoNew Windsor
SDQ - SWF
SDQSWF
Santo Domingo Las Americas
Thu 12/19
7:58 am-5:50 pm
1 stop10h 52m
New Windsor Stewart
Fri 1/3
11:46 am-9:57 am
3 stops21h 11m
NassauNew Windsor
NAS - SWF
NASSWF
Nassau Intl
Sun 1/5
4:00 pm-5:37 pm
1 stop25h 37m
New Windsor Stewart
Sun 1/12
6:44 pm-4:25 pm
1 stop21h 41m
Santiago de los CaballerosNew Windsor
STI - SWF
STISWF
Santiago de los Caballeros
Sun 12/15
10:54 am-12:05 pm
1 stop26h 11m
New Windsor Stewart
Mon 12/30
6:27 pm-9:59 am
1 stop14h 32m
OranjestadNew Windsor
AUA - SWF
AUASWF
Oranjestad Reina Beatrix
Sun 12/22
12:35 pm-5:05 pm
3 stops29h 30m
New Windsor Stewart
Tue 12/31
6:15 pm-7:05 am
3 stops35h 50m
San JuanNew Windsor
SJU - SWF
SJUSWF
San Juan Luis Munoz Marin Intl
Thu 12/5
9:13 pm-12:05 pm
1 stop15h 52m
Santo DomingoNew Windsor
SDQ - SWF
SDQSWF
Santo Domingo Las Americas
Thu 12/5
6:29 pm-12:05 pm
1 stop18h 36m
Montego BayNew Windsor
MBJ - SWF
MBJSWF
Montego Bay Sangster Intl
Thu 12/5
2:38 pm-12:05 pm
1 stop21h 27m
OranjestadNew Windsor
AUA - SWF
AUASWF
Oranjestad Reina Beatrix
Thu 12/5
4:40 pm-12:05 pm
1 stop20h 25m
Santiago de los CaballerosNew Windsor
STI - SWF
STISWF
Santiago de los Caballeros
Sun 12/15
10:54 am-12:05 pm
1 stop26h 11m
Currently, October is the cheapest month in which you can book a flight from Caribbean Islands to New Windsor (average of $109). Flying from Caribbean Islands to New Windsor in December is currently the most expensive (average of $197). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.