
Cheap Flights to Caribbean from $50 (2025/2026)
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Santo Domingo
Flights
How Much Does it Cost To Fly To Caribbean?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
FLL
Fort Lauderdale - Hollywood Intl.
SJU
Luis Munoz Marin Intl.
$91 Roundtrip, found 9 hours ago
$91
Roundtrip
found 9 hours ago
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$183 Roundtrip, found 4 hours ago
$183
Roundtrip
found 4 hours ago
FLL
Fort Lauderdale - Hollywood Intl.
AUA
Queen Beatrix Intl.
$189 Roundtrip, found 3 hours ago
$189
Roundtrip
found 3 hours ago
FLL
Fort Lauderdale - Hollywood Intl.
PUJ
Punta Cana Intl.
$196 Roundtrip, just found
$196
Roundtrip
just found
FLL
Fort Lauderdale - Hollywood Intl.
MBJ
Sir Donald Sangster Intl.
$212 Roundtrip, just found
$212
Roundtrip
just found
FLL
Fort Lauderdale - Hollywood Intl.
KIN
Norman Manley Intl.
$235 Roundtrip, found 4 hours ago
$235
Roundtrip
found 4 hours ago
FLL
Fort Lauderdale - Hollywood Intl.
SDQ
Las Americas Intl.
$236 Roundtrip, found 17 hours ago
$236
Roundtrip
found 17 hours ago
FLL
Fort Lauderdale - Hollywood Intl.
STI
Cibao Intl.
$246 Roundtrip, found 1 hour ago
$246
Roundtrip
found 1 hour ago
Origin | Destination | Travel Dates | Flights From* |
---|---|---|---|
JFK | San Juan | May 17 to May 21 | $188 |
YYZ | Nassau | June 1 to June 12 | $258 |
FLL | Piarco | May 19 to May 25 | $304 |
MIA | Kingston | May 19 to May 23 | $305 |
MIA | Santiago de los Caballeros | June 17 to June 25 | $309 |
PHL | Piarco | May 17 to June 16 | $427 |
LGW | San Juan | May 26 to June 25 | $727 |
JFK | West End | May 26 to May 28 | $758 |
JFK | West End | May 26 to May 28 | $758 |
YYZ | West End | May 18 to May 20 | $831 |
LHR | Montego Bay | May 20 to June 19 | $856 |
LHR | Kingston | June 11 to July 2 | $883 |
BKK | San Juan | June 14 to July 4 | $1,476 |
BKK | Piarco | June 15 to July 16 | $1,684 |
BKK | Punta Cana | August 10 to August 16 | $1,944 |
Origin | Destination | Travel Dates | Flights From* |
---|---|---|---|
FLL | Punta Cana | May 9 to May 15 | $196 |
EWR | San Juan | May 9 to May 19 | $198 |
FLL | Santo Domingo | May 9 to May 17 | $242 |
MIA | Nassau | May 9 to May 11 | $295 |
EWR | Santo Domingo | May 10 to May 14 | $349 |
JFK | Oranjestad | May 10 to May 17 | $357 |
EWR | Oranjestad | May 11 to May 16 | $357 |
MIA | Montego Bay | May 11 to May 25 | $374 |
LGA | Kingston | May 10 to May 31 | $397 |
EWR | Nassau | May 11 to May 28 | $398 |
EWR | Santiago de los Caballeros | May 11 to May 13 | $409 |
EWR | Kingston | May 10 to May 31 | $418 |
JFK | Piarco | May 11 to May 22 | $479 |
BOS | Kingston | May 9 to May 12 | $481 |
JFK | Kingston | May 11 to August 27 | $499 |
Best Caribbean Flight and Hotel Packages
Price found within the past 48 hours. Click for updated prices.



Travelers ❤️ These Caribbean 🏨

Hotel El Convento
100 Cristo St, San Juan
Stay at this 4.5-star luxury hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Pan American Pier are located nearby.
8.6/10 Excellent! (1,001 reviews)
"El Convento is always a great choice for Old San Juan. Our room this time did have a disagreeable view of the squalid property’s roof which was next door. Management could not move us but were very apologetic and sincere in taking our concerns seriously. We always stay at El Convento."
Reviewed on Apr 27, 2025

British Colonial - Nassau
Number One Bay St, Nassau
Stay at this 4-star beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 8 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Junkanoo Beach and Aquaventure are located nearby.
8.4/10 Very Good! (1,530 reviews)
"The property is great but the area surrounding the property shuts down once cruise ships leave port which gives the impression they cater to the ship clientele needs."
Reviewed on Apr 28, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street, San Juan, Puerto Rico
Stay at this 4-star business-friendly hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Pan American Pier are located nearby.
8.8/10 Excellent! (913 reviews)
"Very clean, friendly staff, great restaurant on-site, walkable to points of interest"
Reviewed on Apr 30, 2025
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The Reef at Atlantis
Paradise Beach Drive, Paradise Island, New Providence
Stay at this 4.5-star luxury resort in Paradise Island. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Aquaventure and Cabbage Beach are located nearby.
8.8/10 Excellent! (1,327 reviews)
"Great time at The Reef in Atlantis. Highly recommend if you’re looking for something a bit quieter than the Royal Tower."
Reviewed on May 1, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
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