
Cheap Flights to Caribbean from $69 (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.
BWI
Baltimore Washington Intl. Thurgood Marshall
SJU
Luis Munoz Marin Intl.
$138 Roundtrip, just found
$138
Roundtrip
just found
BWI
Baltimore Washington Intl. Thurgood Marshall
SJU
Luis Munoz Marin Intl.
$138 Roundtrip, just found
$138
Roundtrip
just found
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$140 Roundtrip, found 17 hours ago
$140
Roundtrip
found 17 hours ago
EWR
Newark Liberty Intl. Airport
SJU
Luis Munoz Marin Intl.
$141 Roundtrip, found 7 hours ago
$141
Roundtrip
found 7 hours ago
BWI
Baltimore Washington Intl. Thurgood Marshall
SJU
Luis Munoz Marin Intl.
$205 Roundtrip, found 5 days ago
$205
Roundtrip
found 5 days ago
EWR
Newark Liberty Intl. Airport
SDQ
Las Americas Intl.
$231 Roundtrip, found 2 hours ago
$231
Roundtrip
found 2 hours ago
BWI
Baltimore Washington Intl. Thurgood Marshall
PUJ
Punta Cana Intl.
$244 Roundtrip, just found
$244
Roundtrip
just found
BWI
Baltimore Washington Intl. Thurgood Marshall
MBJ
Sir Donald Sangster Intl.
$247 Roundtrip, found 15 hours ago
$247
Roundtrip
found 15 hours ago
BWI
Baltimore Washington Intl. Thurgood Marshall
SJU
Luis Munoz Marin Intl.
$280 Roundtrip, found 4 days ago
$280
Roundtrip
found 4 days ago
BWI
Baltimore Washington Intl. Thurgood Marshall
SDQ
Las Americas Intl.
$288 Roundtrip, found 5 days ago
$288
Roundtrip
found 5 days ago
BWI
Baltimore Washington Intl. Thurgood Marshall
SJU
Luis Munoz Marin Intl.
$292 Roundtrip, just found
$292
Roundtrip
just found
Origin | Destination | Travel Dates | Flights From* |
---|---|---|---|
EWR | Nassau | September 27 to October 11 | $310 |
JFK | Nassau | September 19 to September 25 | $310 |
JFK | Nassau | September 19 to September 25 | $310 |
JFK | Kingston | November 16 to November 18 | $376 |
LGW | Punta Cana | November 18 to December 4 | $722 |
LHR | Oranjestad | September 22 to October 7 | $891 |
Origin | Destination | Travel Dates | Flights From* |
---|---|---|---|
EWR | San Juan | August 31 to September 10 | $200 |
FLL | Santo Domingo | August 31 to September 3 | $206 |
JFK | San Juan | August 31 to September 10 | $248 |
FLL | Montego Bay | August 31 to September 3 | $286 |
FLL | Kingston | August 30 to September 3 | $339 |
EWR | Punta Cana | August 29 to September 10 | $375 |
EWR | Montego Bay | August 30 to September 4 | $396 |
EWR | Oranjestad | August 31 to September 4 | $403 |
BOS | Punta Cana | August 30 to September 5 | $445 |
JFK | Santo Domingo | August 31 to September 4 | $456 |
EWR | Santiago de los Caballeros | August 30 to September 7 | $478 |
BOS | Nassau | August 31 to September 6 | $478 |
EWR | Piarco | August 31 to September 6 | $487 |
JFK | Montego Bay | August 30 to September 4 | $570 |
EWR | Kingston | August 31 to September 9 | $621 |
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.
8.8/10 Excellent! (1,002 reviews)
"Great stay very nice location"
Reviewed on Aug 25, 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 Cable Beach are located nearby.

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.
9/10 Wonderful! (1,119 reviews)
"Great"
Reviewed on Aug 24, 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 Junkanoo Beach and Cable Beach are located nearby.
8.8/10 Excellent! (1,417 reviews)
"All good"
Reviewed on Aug 25, 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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