
Cheap Flights to Caribbean from $106 (2026/2027)
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Punta Cana
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.
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$231 Roundtrip, found 2 days ago
$231
Roundtrip
found 2 days ago
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$232 Roundtrip, just found
$232
Roundtrip
just found
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$237 Roundtrip, just found
$237
Roundtrip
just found
JFK
John F. Kennedy Intl.
NAS
Lynden Pindling Intl.
$313 Roundtrip, found 5 hours ago
$313
Roundtrip
found 5 hours ago
JFK
John F. Kennedy Intl.
SDQ
Las Americas Intl.
$322 Roundtrip, found 1 hour ago
$322
Roundtrip
found 1 hour ago
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$325 Roundtrip, found 15 hours ago
$325
Roundtrip
found 15 hours ago
JFK
John F. Kennedy Intl.
PUJ
Punta Cana Intl.
$344 Roundtrip, found 3 hours ago
$344
Roundtrip
found 3 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | October 29 to October 30 | $222 |
| JFK | Nassau | November 16 to November 17 | $313 |
| JFK | Santo Domingo | November 3 to November 11 | $322 |
| JFK | Montego Bay | November 2 to November 5 | $325 |
| EWR | Montego Bay | September 27 to October 9 | $325 |
| EWR | Punta Cana | October 27 to October 31 | $335 |
| JFK | Punta Cana | November 7 to November 11 | $338 |
| EWR | Nassau | October 15 to October 21 | $341 |
| JFK | Kingston | October 5 to October 9 | $367 |
| JFK | Oranjestad | September 28 to October 1 | $383 |
| JFK | Santiago de los Caballeros | September 1 to September 2 | $395 |
| JFK | Santiago de los Caballeros | September 1 to September 2 | $395 |
| JFK | Piarco | September 29 to November 5 | $425 |
| JFK | West End | September 21 to September 27 | $467 |
| JFK | West End | September 21 to September 27 | $467 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | August 14 to August 19 | $426 |
| JFK | San Juan | August 14 to August 19 | $426 |
| EWR | San Juan | August 15 to August 27 | $437 |
| EWR | Piarco | August 15 to August 21 | $453 |
| EWR | Piarco | August 15 to August 21 | $453 |
| JFK | Montego Bay | August 16 to August 20 | $499 |
| JFK | Montego Bay | August 16 to August 20 | $499 |
| JFK | Santiago de los Caballeros | August 14 to September 2 | $516 |
| JFK | Kingston | August 16 to August 22 | $596 |
| EWR | Montego Bay | August 16 to August 27 | $598 |
| EWR | Santiago de los Caballeros | August 16 to September 20 | $638 |
| JFK | Piarco | August 14 to August 22 | $665 |
| BOS | Montego Bay | August 14 to August 26 | $706 |
| EWR | Santo Domingo | August 16 to August 22 | $807 |
| EWR | Kingston | August 14 to August 23 | $1,003 |
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
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 Condado Beach are located nearby.
9.2/10 Wonderful! (1,022 reviews)
"Beautiful property in the heart of Old San Juan! A must stay!"
Reviewed on Aug 10, 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 6 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Junkanoo Beach and Aquaventure are located nearby.

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 Condado Beach are located nearby.
9/10 Wonderful! (1,849 reviews)
"The only complaint is the overcharhing fee. I call Expedia and asked if there was going to be an extra fee at our arrival and was told that everithing was paid a big lie. Very dissapoint it. I will think twice next time i book a trip with Expidia . The customer service person was in Mexico."
Reviewed on Aug 10, 2026
Save an average of 15% on thousands of hotels when you're signed in

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 Aquaventure and Atlantis Casino are located nearby.
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.






