$106 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $106 One Way, $252 Round Trip
$252 return flights and $106 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.
JFK
New York
SJU
San Juan
$252 Roundtrip, just found
$252
Roundtrip
just found
JFK
New York
SJU
San Juan
$257 Roundtrip, just found
$257
Roundtrip
just found
JFK
New York
SJU
San Juan
$261 Roundtrip, found 13 hours ago
$261
Roundtrip
found 13 hours ago
EWR
New York
SJU
San Juan
$266 Roundtrip, just found
$266
Roundtrip
just found
EWR
New York
SJU
San Juan
$279 Roundtrip, found 1 day ago
$279
Roundtrip
found 1 day ago
EWR
New York
SJU
San Juan
$285 Roundtrip, found 2 hours ago
$285
Roundtrip
found 2 hours ago
EWR
New York
SJU
San Juan
$295 Roundtrip, found 1 day ago
$295
Roundtrip
found 1 day ago
JFK
New York
NAS
Nassau
$319 Roundtrip, found 2 days ago
$319
Roundtrip
found 2 days ago
EWR
New York
SDQ
Santo Domingo
$319 Roundtrip, found 12 hours ago
$319
Roundtrip
found 12 hours ago
EWR
New York
MBJ
Montego Bay
$320 Roundtrip, found 4 hours ago
$320
Roundtrip
found 4 hours ago
JFK
New York
SDQ
Santo Domingo
$320 Roundtrip, just found
$320
Roundtrip
just found
JFK
New York
PUJ
Punta Cana
$323 Roundtrip, found 5 hours ago
$323
Roundtrip
found 5 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Montego Bay | August 22 to September 23 | $420 |
| JFK | San Juan | August 22 to August 28 | $458 |
| JFK | San Juan | August 22 to August 28 | $458 |
| EWR | Piarco | August 23 to September 6 | $464 |
| JFK | Kingston | August 21 to August 31 | $528 |
| JFK | Kingston | August 21 to August 31 | $528 |
| JFK | Santiago de los Caballeros | August 22 to September 19 | $534 |
| JFK | Santiago de los Caballeros | August 22 to September 19 | $534 |
| JFK | Santo Domingo | August 23 to September 2 | $555 |
| JFK | Punta Cana | August 23 to August 27 | $557 |
| JFK | Punta Cana | August 23 to August 27 | $557 |
| JFK | Piarco | August 22 to September 8 | $600 |
| JFK | Nassau | August 23 to August 26 | $638 |
| EWR | Nassau | August 22 to August 26 | $645 |
| JFK | Oranjestad | August 21 to August 25 | $664 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
Paradise Island Drive Paradise Island New Providence
The price is $383 total per night from Aug 19 to Aug 20
$383 total
per night
Aug 19 - Aug 20
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! (2,405 reviews)
"This hotel is very cute and comfy. It also has a great perk of going to Atlantis each day of my stay the staff are so friendly and helpful. Great place to stay for families and singles . The complimentary breakfast was a great money saver in the bahamas. I will definitely be using them again."
Reviewed on Aug 17, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
The price is $140 total per night from Aug 30 to Aug 31
$140 total
per night
Aug 30 - Aug 31
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 (2,436 reviews)
"."
Reviewed on Aug 18, 2026
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
The price is $340 total per night from Aug 25 to Aug 26
$340 total
per night
Aug 25 - Aug 26
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 ...
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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
The price is $210 total per night from Sep 9 to Sep 10
$210 total
per night
Sep 9 - Sep 10
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! (1,961 reviews)
"Clean room, nice pool and restaurants."
Reviewed on Aug 17, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
The price is $306 total per night from Aug 23 to Aug 24
$306 total
per night
Aug 23 - Aug 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! (1,005 reviews)
"VERY CLEAN ROOM AND GROUNDS. BEAUTIFUL PAINT. THE PEOPLE at the desk were very helpful, a lot of questions answered. They steamed my milk for my Coffee in the morning. Free parking. NO HASSLE BEACH EXPERIENCE. SUNSET IS AMAZING."
Reviewed on Aug 16, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
The price is $612 total per night from Aug 19 to Aug 20
$612 total
per night
Aug 19 - Aug 20
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 ...
8.8/10 Excellent! (1,006 reviews)
"The room was semi cleaned every day had to call maintenance to fix ac. When booked thru expedia I assume I did not get the same side of building we normally stay in so it was an additional 500.00 to move to the newer building. When asked to stay an additional 30 min to save from sitting in lobby ..."
Reviewed on Aug 18, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
The price is $350 total per night from Sep 15 to Sep 16
$350 total
per night
Sep 15 - Sep 16
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. ...
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
$247 nightly
The price is $270 total per night from Sep 1 to Sep 2
$270 total
Sep 1 - Sep 2
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! (1,010 reviews)
"The most wonderful hotel in the heart of old San Juan. Steeped in history, it has been modernised enough to give you what you need without removing it’s original charm. The staff are incredibly friendly and helpful and, staying off season, the price was a bargain."
Reviewed on Aug 18, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $260 total per night from Sep 7 to Sep 8
$260 total
Sep 7 - Sep 8
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! (2,915 reviews)
"The property is nicely centered. It's great that it has its own private beach, and pool. The staff are very friendly and accommodating."
Reviewed on Aug 18, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$187 nightly
The price is $207 total per night from Aug 23 to Aug 24
$207 total
Aug 23 - Aug 24
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! (1,866 reviews)
"This is my second time at Hotel Rumbao. My family loved the suite. The beds are so comfortable. I love staying at Rumbao. The staff is professional and friendly."
Reviewed on Aug 18, 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 ...
9/10 Wonderful! (1,658 reviews)
"overall we had a good stay. Good- Reef is still nice and quiet and away from the business of the other hotels. Beach, pools and waterpark were great. However, we had some issues within the room with fridge (not cold enough), running out of towels at beach, beach chair covers broken and a few other ..."
Reviewed on Aug 17, 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.
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Carretera Bávaro Km. 1 Punta Cana La Altagracia
The price is $287 total per night from Aug 25 to Aug 26
$287 total
per night
Aug 25 - Aug 26
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 ...
8.2/10 Very Good! (6,029 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"Muy mala experiencia, no recomendaria este hotel."
Reviewed on Aug 18, 2026
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! (1,549 reviews)
Families like: Outdoor pools, free waterpark access, kids club, playground
Travelers say...
"All was good"
Reviewed on Jan 15, 2026
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Majestic Elegance Punta Cana - All Inclusive
Playa Bavaro - Punta Cana Punta Cana La Altagracia
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 restaurant in our reviews. ...
9/10 Wonderful! (4,948 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"Great resot! Recommend 100%"
Reviewed on Aug 18, 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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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.