Cheap Flights to Caribbean from $83 (2026/2027)
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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.
EWR
Newark Liberty Intl. Airport
SJU
Luis Munoz Marin Intl.
$166 Roundtrip, just found
$166
Roundtrip
just found
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$166 Roundtrip, just found
$166
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
SJU
Luis Munoz Marin Intl.
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
EWR
Newark Liberty Intl. Airport
AUA
Queen Beatrix Intl.
$238 Roundtrip, found 3 days ago
$238
Roundtrip
found 3 days ago
EWR
Newark Liberty Intl. Airport
STI
Cibao Intl.
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
EWR
Newark Liberty Intl. Airport
SJU
Luis Munoz Marin Intl.
$247 Roundtrip, found 2 hours ago
$247
Roundtrip
found 2 hours ago
EWR
Newark Liberty Intl. Airport
SJU
Luis Munoz Marin Intl.
$247 Roundtrip, just found
$247
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
SDQ
Las Americas Intl.
$272 Roundtrip, just found
$272
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
SJU
Luis Munoz Marin Intl.
$276 Roundtrip, found 2 hours ago
$276
Roundtrip
found 2 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | April 14 to April 16 | $202 |
| LGA | Oranjestad | March 17 to March 24 | $238 |
| EWR | Santo Domingo | May 12 to May 16 | $272 |
| JFK | Montego Bay | April 9 to April 17 | $278 |
| EWR | Montego Bay | May 6 to May 13 | $288 |
| JFK | Santo Domingo | May 11 to May 12 | $304 |
| JFK | Santiago de los Caballeros | April 26 to April 26 | $323 |
| EWR | Piarco | March 10 to March 24 | $338 |
| JFK | Piarco | March 17 to March 19 | $345 |
| MIA | West End | April 18 to April 25 | $349 |
| EWR | Nassau | April 12 to April 16 | $353 |
| EWR | Nassau | April 12 to April 16 | $353 |
| JFK | Nassau | May 30 to June 6 | $360 |
| JFK | West End | March 13 to March 19 | $399 |
| JFK | Kingston | May 7 to May 9 | $431 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | Santo Domingo | March 1 to March 6 | $322 |
| EWR | Santo Domingo | March 1 to March 6 | $322 |
| EWR | Punta Cana | February 28 to March 5 | $327 |
| EWR | Montego Bay | March 1 to March 7 | $358 |
| JFK | Santo Domingo | March 1 to March 6 | $360 |
| LGA | Piarco | February 28 to March 7 | $368 |
| EWR | Nassau | February 28 to March 3 | $373 |
| EWR | Nassau | February 28 to March 3 | $373 |
| EWR | Piarco | March 1 to March 11 | $382 |
| JFK | Santiago de los Caballeros | March 1 to March 12 | $395 |
| JFK | Punta Cana | March 1 to March 4 | $397 |
| JFK | West End | March 1 to March 7 | $419 |
| JFK | West End | March 1 to March 7 | $419 |
| JFK | Montego Bay | February 27 to March 2 | $424 |
| JFK | Nassau | March 1 to March 3 | $469 |
Best Caribbean Flight and Hotel Packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Sunset at the Palms Resort - Adults Only - All Inclusive
Apr 27 - May 2
5 night stay
Boston (BOS) to Montego Bay (MBJ)
Spirit Airlines • Non-stop • Coach
Montego Bay (MBJ) to Boston (BOS)
Frontier Airlines • Non-stop • Coach
Price was $3,028, price is now $1,244 per person
$1,244
per person
found 1 day ago
Travelers ❤️ These Caribbean 🏨
Hotel El Convento
100 Cristo St San Juan
Book a stay at this 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.
9/10 Wonderful! (1,000 reviews)
Beautiful property in a perfect location if you plan to visit Old San Juan. Restaurant is wonderful.
Reviewed on Feb 14, 2026
British Colonial - Nassau
Number One Bay St Nassau
Book a stay at this 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 Cable Beach and Pirates of Nassau Museum are located nearby.
8.6/10 Excellent! (2,281 reviews)
We had a wonderful stay at the British Colonial. What stood out most was the consistency of service, especially over an extremely busy holiday weekend. Every interaction reflected professionalism, warmth, and genuine care. Thank you to Charles and his team for their support throughout the week. We ...
Reviewed on Feb 22, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Book a stay at this 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! (1,532 reviews)
Room was not clean but very well apointed. The breakfast was fantastic. Parking is terrible.
Reviewed on Feb 20, 2026
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The Reef at Atlantis
Paradise Beach Drive Paradise Island New Providence
Book a stay at this 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 Cable Beach and Aquaventure are located nearby.
9/10 Wonderful! (1,422 reviews)
The staff were all friendly and helpful. The rooms were all well appointed and clean. The amenities were plenty to keep us and our 2 teenage boys occupied. Beaches were beautiful. The shuttle was not always timely, but they were free of charge. The restaurants were numerous, but the food was just ...
Reviewed on Feb 21, 2026
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.