$105 Cheap flights to Caribbean
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
Top places to visit in Caribbean
Cheap flights to Caribbean from $105 One Way, $260 Round Trip
$260 return flights and $105 one-way flights to Caribbean were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
EWR
New York
PUJ
Punta Cana
$260 Roundtrip, found 3 hours ago
$260
Roundtrip
found 3 hours ago
EWR
New York
SDQ
Santo Domingo
$260 Roundtrip, found 6 hours ago
$260
Roundtrip
found 6 hours ago
JFK
New York
SJU
San Juan
$272 Roundtrip, found 3 days ago
$272
Roundtrip
found 3 days ago
EWR
New York
SJU
San Juan
$284 Roundtrip, found 21 hours ago
$284
Roundtrip
found 21 hours ago
JFK
New York
SJU
San Juan
$292 Roundtrip, found 1 hour ago
$292
Roundtrip
found 1 hour ago
EWR
New York
AUA
Oranjestad
$301 Roundtrip, found 4 days ago
$301
Roundtrip
found 4 days ago
EWR
New York
SJU
San Juan
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
JFK
New York
NAS
Nassau
$320 Roundtrip, found 5 days ago
$320
Roundtrip
found 5 days ago
EWR
New York
SJU
San Juan
$336 Roundtrip, found 1 day ago
$336
Roundtrip
found 1 day ago
JFK
New York
MBJ
Montego Bay
$338 Roundtrip, found 1 day ago
$338
Roundtrip
found 1 day ago
JFK
New York
PUJ
Punta Cana
$343 Roundtrip, found 1 day ago
$343
Roundtrip
found 1 day ago
JFK
New York
AUA
Oranjestad
$374 Roundtrip, found 4 hours ago
$374
Roundtrip
found 4 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | San Juan | September 19 to September 25 | $357 |
| JFK | San Juan | September 19 to September 23 | $357 |
| EWR | San Juan | September 19 to September 25 | $357 |
| JFK | Nassau | September 19 to September 26 | $375 |
| JFK | Nassau | September 19 to September 26 | $375 |
| EWR | Nassau | September 20 to September 24 | $395 |
| JFK | Punta Cana | September 19 to September 24 | $491 |
| JFK | Punta Cana | September 19 to September 24 | $491 |
| EWR | Santo Domingo | September 20 to September 30 | $492 |
| JFK | Santiago de los Caballeros | September 18 to October 3 | $500 |
| JFK | Santiago de los Caballeros | September 18 to October 3 | $500 |
| JFK | Oranjestad | September 20 to September 24 | $524 |
| JFK | Santo Domingo | September 20 to October 20 | $574 |
| JFK | Piarco | September 19 to September 27 | $580 |
| JFK | Montego Bay | September 18 to September 26 | $606 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
Paradise Island Drive Paradise Island New Providence
Fully refundable
The price is $366 total per night from Oct 4 to Oct 5
$366 total
per night
Oct 4 - Oct 5
Book a stay at this business-friendly hotel in Paradise Island. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
8.4/10 Very Good! (2,442 reviews)
"Very good location!"
Reviewed on Sep 11, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
The price is $138 total per night from Sep 12 to Sep 13
$138 total
per night
Sep 12 - Sep 13
Stay at this hotel in Carolina. Enjoy free WiFi, 2 restaurants, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.4/10 (2,439 reviews)
"Deberían darle más mantenimiento a las habitaciones"
Reviewed on Sep 11, 2026
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
Book a stay at this beach hotel in Nassau. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
7.6/10 Good! (2,446 reviews)
"They served the same or similar food three times a day every day."
Reviewed on Sep 11, 2026
Save an average of 15% on thousands of hotels when you're signed in
Meridian Inn
Dover St. Lawrence Gap Christ Church
Stay at this hotel in St. Lawrence Gap. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (861 reviews)
"Stayed 2 nights while waiting for flights after a cruise. Wonderful place on the Ocean. Great pool and friendly staff. Comfortable bed. Would certainly stay here again as it’s a great price when you do not want an all inclusive resort. I gave cleanliness a 5* even though the bathroom had tiny ants ..."
Reviewed on Apr 25, 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.
Our Top Caribbean Apartment Hotels
Simpson Bay Resort, Marina & Spa
Billy Folly Road 37 Simpson Bay
Fully refundableReserve now, pay when you stay
The price is $190 total per night from Sep 13 to Sep 14
$190 total
per night
Sep 13 - Sep 14
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
The price is $340 total per night from Sep 23 to Sep 24
$340 total
per night
Sep 23 - Sep 24
Book a stay at this beach hotel in Noord. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.6/10 Exceptional! (1,000 reviews)
"Highly recommend!"
Reviewed on Sep 10, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
The price is $604 total per night from Sep 12 to Sep 13
$604 total
per night
Sep 12 - Sep 13
Book a stay at this spa resort in Noord. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions ...
Save an average of 15% on thousands of hotels when you're signed in
Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
The price is $350 total per night from Oct 12 to Oct 13
$350 total
per night
Oct 12 - Oct 13
Book a stay at this beach hotel in Oranjestad. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,848 reviews)
"We liked that the pool area was strictly maintained and towels were readily available. The food at the Sports Bar was not very appealing. It was mostly overcooked and not enough variety. We had instances with water bugs more this time than before. We know this is the tropics, but maintenance should ..."
Reviewed on Sep 10, 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.
Score Epic Caribbean Accommodation Deals
Hotel El Convento
100 Cristo St San Juan
Fully refundableReserve now, pay when you stay
The price is $240 total per night from Sep 23 to Sep 24
$240 total
per night
Sep 23 - Sep 24
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 ...
9.2/10 Wonderful! (1,003 reviews)
"El mejor lugar para hospedarse en todo el VSJ!"
Reviewed on Sep 10, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
The price is $253 total per night from Sep 20 to Sep 21
$253 total
per night
Sep 20 - Sep 21
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 ...
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
The price is $201 total per night from Sep 20 to Sep 21
$201 total
per night
Sep 20 - Sep 21
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 ...
9/10 Wonderful! (1,924 reviews)
"Great place"
Reviewed on Sep 11, 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 ...
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.
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Carretera Bávaro Km. 1 Punta Cana La Altagracia
The price is $279 total per night from Oct 1 to Oct 2
$279 total
per night
Oct 1 - Oct 2
Book a stay at this luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our ...
Majestic Colonial Punta Cana - All Inclusive
Carretera El Macao Punta Cana La Altagracia
Book a stay at this beach property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Dreams Rose Hall Resort & Spa - All Inclusive
Rose Hall Montego Bay Saint James
Book a stay at this luxury resort in Montego Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our ...
8.4/10 Very Good! (1,484 reviews)
Families like: Outdoor pools, free waterpark access, kids club, playground
Travelers say...
"All was good"
Reviewed on Jan 15, 2026
Save an average of 15% on thousands of hotels when you're signed in
The Royal at Atlantis
Paradise Beach Drive Paradise Island New Providence
Book a stay at this beach resort in Paradise Island. Enjoy free WiFi, 14 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (2,995 reviews)
Families like: Outdoor pools, free waterpark access, kids club, playground
Travelers say...
"Very nice"
Reviewed on Sep 11, 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.
Need a Car For After Your Flight?
Economy
Chevrolet Spark
Compact
Ford Focus
Midsize
Toyota Corolla
SUV
Jeep Compass
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.