$109 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $109 One Way, $256 Round Trip
$256 return flights and $109 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
SJU
San Juan
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
EWR
New York
SDQ
Santo Domingo
$276 Roundtrip, found 4 days ago
$276
Roundtrip
found 4 days ago
JFK
New York
SJU
San Juan
$292 Roundtrip, found 3 hours ago
$292
Roundtrip
found 3 hours ago
EWR
New York
AUA
Oranjestad
$293 Roundtrip, found 1 hour ago
$293
Roundtrip
found 1 hour ago
JFK
New York
SJU
San Juan
$297 Roundtrip, just found
$297
Roundtrip
just found
EWR
New York
PUJ
Punta Cana
$299 Roundtrip, found 1 hour ago
$299
Roundtrip
found 1 hour ago
EWR
New York
AUA
Oranjestad
$323 Roundtrip, found 3 days ago
$323
Roundtrip
found 3 days ago
JFK
New York
AUA
Oranjestad
$323 Roundtrip, found 11 hours ago
$323
Roundtrip
found 11 hours ago
JFK
New York
NAS
Nassau
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
EWR
New York
SJU
San Juan
$336 Roundtrip, found 5 days ago
$336
Roundtrip
found 5 days ago
JFK
New York
STI
Santiago de los Caballeros
$344 Roundtrip, found 18 hours ago
$344
Roundtrip
found 18 hours ago
JFK
New York
PUJ
Punta Cana
$354 Roundtrip, found 4 days ago
$354
Roundtrip
found 4 days ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Nassau | September 19 to September 26 | $391 |
| EWR | Piarco | September 18 to September 23 | $488 |
| EWR | Piarco | September 18 to September 23 | $488 |
| JFK | Oranjestad | September 20 to September 23 | $489 |
| JFK | Oranjestad | September 20 to September 23 | $489 |
| LGA | Punta Cana | September 18 to September 20 | $498 |
| EWR | San Juan | September 19 to September 22 | $501 |
| EWR | Santo Domingo | September 20 to September 30 | $547 |
| JFK | Santiago de los Caballeros | September 20 to October 4 | $555 |
| JFK | Santiago de los Caballeros | September 20 to October 4 | $555 |
| JFK | Santo Domingo | September 18 to October 8 | $569 |
| JFK | Montego Bay | September 20 to September 27 | $574 |
| EWR | Santiago de los Caballeros | September 19 to October 6 | $574 |
| JFK | Piarco | September 20 to September 25 | $611 |
| JFK | Kingston | September 20 to October 4 | $998 |
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
$359 nightly
The price is $396 total per night from Sep 20 to Sep 21
$396 total
Sep 20 - Sep 21
Total with taxes and fees
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 ...
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $138 total per night from Sep 16 to Sep 17
$138 total
Sep 16 - Sep 17
Total with taxes and fees
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. ...
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! (2,450 reviews)
"Ok, so I gave it 5 stars, However there are a few things that can be improved upon. First, there is a "great need" for a serious remodel or updates! Wife and her first husband was here 26 years ago. When we got here, she told me that it still looks the same!!!!! Also there needs to be a snack or ..."
Reviewed on Sep 14, 2026
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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
$178 nightly
The price is $186 total per night from Sep 16 to Sep 17
$186 total
Sep 16 - Sep 17
Total with taxes and fees
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 ...
9/10 Wonderful! (2,033 reviews)
"Old resort being maintained."
Reviewed on Sep 15, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
$320 nightly
The price is $360 total per night from Sep 17 to Sep 18
$360 total
Sep 17 - Sep 18
Total with taxes and fees
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! (1,001 reviews)
"The Room and hotel is great but the restaurant"
Reviewed on Sep 13, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$534 nightly
The price is $604 total per night from Sep 16 to Sep 17
$604 total
Sep 16 - Sep 17
Total with taxes and fees
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
$293 nightly
The price is $341 total per night from Oct 14 to Oct 15
$341 total
Oct 14 - Oct 15
Total with taxes and fees
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! (1,850 reviews)
"Loved the hotel, great location. Rooms are super spacious and comfortable and they mandate the AC is never turned off in the room! Staff is pleasant, would definitely come again."
Reviewed on Sep 15, 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
$298 nightly
The price is $325 total per night from Sep 16 to Sep 17
$325 total
Sep 16 - Sep 17
Total with taxes and fees
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! (1,005 reviews)
"The beautiful building and historic structure"
Reviewed on Sep 13, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$231 nightly
The price is $253 total per night from Sep 16 to Sep 17
$253 total
Sep 16 - Sep 17
Total with taxes and fees
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 ...
8.6/10 Excellent! (3,036 reviews)
"The hotel is very pretty and clean, The staff is also very helpful. The rooms have no mirrors and the was not shower curtain for the shower. The restaurants are also very expensive. The Wood Rogers Tavern was the only thing the was open during my stay and it was good. The Brunch was $80 with tax ..."
Reviewed on Sep 15, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $201 total per night from Sep 27 to Sep 28
$201 total
Sep 27 - Sep 28
Total with taxes and fees
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! (1,930 reviews)
"Excellent stay for me and my teenage daughter. Every interaction was very pleasant, friendly, and helpful. Property has vast options for relaxing in calm quiet peace, or having fun throughout the day and night. Food options were all amazing. We had dinner at a different restaurant each night and ..."
Reviewed on Sep 14, 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
$218 nightly
The price is $279 total per night from Oct 1 to Oct 2
$279 total
Oct 1 - Oct 2
Total with taxes and fees
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! (3,012 reviews)
Families like: Outdoor pools, free waterpark access, kids club, playground
Travelers say...
"Exploring the fishtanks dolfinn tanks ,tortious , manta rays reg fish amazing property . water park is a major plus"
Reviewed on Sep 15, 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.
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Caribbean
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Mix and Match
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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.