$97 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $97 One Way, $252 Round Trip
$252 return flights and $97 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, found 11 hours ago
$252
Roundtrip
found 11 hours ago
EWR
New York
SJU
San Juan
$256 Roundtrip, found 3 days ago
$256
Roundtrip
found 3 days ago
EWR
New York
SJU
San Juan
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
EWR
New York
SJU
San Juan
$275 Roundtrip, found 1 day ago
$275
Roundtrip
found 1 day ago
JFK
New York
SJU
San Juan
$297 Roundtrip, found 5 days ago
$297
Roundtrip
found 5 days ago
EWR
New York
PUJ
Punta Cana
$305 Roundtrip, just found
$305
Roundtrip
just found
EWR
New York
SDQ
Santo Domingo
$305 Roundtrip, just found
$305
Roundtrip
just found
JFK
New York
SJU
San Juan
$311 Roundtrip, found 21 hours ago
$311
Roundtrip
found 21 hours ago
JFK
New York
MBJ
Montego Bay
$318 Roundtrip, just found
$318
Roundtrip
just found
EWR
New York
MBJ
Montego Bay
$318 Roundtrip, found 3 days ago
$318
Roundtrip
found 3 days ago
JFK
New York
PUJ
Punta Cana
$337 Roundtrip, found 23 hours ago
$337
Roundtrip
found 23 hours ago
JFK
New York
POS
Trinidad
$350 Roundtrip, just found
$350
Roundtrip
just found
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LGA | Piarco | May 23 to May 26 | $403 |
| JFK | Santiago de los Caballeros | May 23 to May 28 | $403 |
| JFK | Santiago de los Caballeros | May 23 to May 28 | $403 |
| JFK | Piarco | May 24 to May 26 | $410 |
| JFK | Santo Domingo | May 24 to May 29 | $410 |
| JFK | San Juan | May 23 to June 2 | $433 |
| EWR | Punta Cana | May 24 to June 3 | $444 |
| EWR | San Juan | May 23 to May 26 | $456 |
| EWR | Santo Domingo | May 24 to May 31 | $460 |
| JFK | Oranjestad | May 22 to May 29 | $463 |
| JFK | Montego Bay | May 22 to May 25 | $468 |
| LGA | Kingston | May 24 to May 29 | $504 |
| JFK | Kingston | May 24 to May 29 | $505 |
| JFK | Punta Cana | May 24 to May 27 | $547 |
| EWR | Montego Bay | May 23 to May 27 | $693 |
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 $352 total per night from May 17 to May 18
$352 total
per night
May 17 - May 18
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! (2,242 reviews)
The room was clean and staff was awesome. The only bad part was the terrible smell of trash in the hallway by the elevator.
Reviewed on May 15, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
The price is $233 total per night from May 17 to May 18
$233 total
per night
May 17 - May 18
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. ...
6.2/10 (2,374 reviews)
Yes
Reviewed on May 16, 2026
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
The price is $374 total per night from May 25 to May 26
$374 total
per night
May 25 - May 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 ...
7.6/10 Good! (2,287 reviews)
The food was overall good, the staff was friendly and helpful.
Reviewed on May 15, 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
$252 nightly
The price is $264 total per night from Jun 15 to Jun 16
$264 total
Jun 15 - Jun 16
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! (1,728 reviews)
I could not have stayed at a better place! Simpson bay is centrally located to all the businesses. All the businesses will call the shuttle to the meeting point for you. It is quite large but by day two I could navigate by foot and the shuttle service is robust. The staff were welcoming accommodating ...
Reviewed on May 15, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
$315 nightly
The price is $354 total per night from May 26 to May 27
$354 total
May 26 - May 27
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! (1,012 reviews)
2 bedrooms for 5 adults with a beach view. Beautiful view of the sunset. The staff was friendly and helpful. Made our reservations to restaurants and tours. The rooms were clean and compact but had all that was needed for comfort-kitchen, dining area, balcony with chairs. Great Views. A roller bed ...
Reviewed on May 15, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$473 nightly
The price is $536 total per night from May 18 to May 19
$536 total
May 18 - May 19
Total with taxes and fees
Book a stay at this beach 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! (1,002 reviews)
Everything was good , they made my vacation Divi Phoenix, friendly helpful very good time
Reviewed on May 16, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
$355 nightly
The price is $403 total per night from Jun 1 to Jun 2
$403 total
Jun 1 - Jun 2
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! (1,994 reviews)
Great hotel and staff
Reviewed on May 12, 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
$292 nightly
The price is $318 total per night from Jun 1 to Jun 2
$318 total
Jun 1 - Jun 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 ...
9/10 Wonderful! (1,005 reviews)
Desde el momento que no se acercamos a la calzada de la calle, la experiencia fue única, el personal de recepción sumamente amable, cordial y respetuoso. Nos indicó las amenidades, horarios y todos los detalles importantes. Un hotel acogedor,súper tranquilo. Las camas súper cómodas. Nos sentimos ...
Reviewed on May 14, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $278 total per night from Jun 1 to Jun 2
$278 total
Jun 1 - Jun 2
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! (2,573 reviews)
it was okay. got there at 5pm and shortly after all the outside restaurants closed, which was a bummer. we ate inside and the food took a while but its okay bc we were on island time. i did find a bone on my cheese flatbread. not sure what happened there. overall room was average. nice location ...
Reviewed on May 16, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$247 nightly
The price is $269 total per night from May 31 to Jun 1
$269 total
May 31 - Jun 1
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! (1,677 reviews)
Good
Reviewed on May 15, 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! (1,477 reviews)
Amazing honestly if somewhere could leave you speechless it’s here. I went with my husband and our two kids and everything was inclusive to all of us I will definitely be coming back!
Reviewed on May 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.
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Carretera Bávaro Km. 1 Punta Cana La Altagracia
$285 nightly
The price is $364 total per night from Jun 1 to Jun 2
$364 total
Jun 1 - Jun 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 ...
8.2/10 Very Good! (5,598 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
Property was great. Zero pool activities! Sub par liquor at the pool. A little better at inside bars and restaurants. Buffet food was ehh! No coffee in the rooms some mornings-or creamer etc.. steak house was hit or miss, long walks to get anywhere. Shows were not great and didn’t start till 10pm ...
Reviewed on May 16, 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. ...
9/10 Wonderful! (6,623 reviews)
Colonial closed, being renovated. Majestic just rebooked to elegance, never let us know to book elsewhere. Elegance is party place, loud music, ok food, and many staff don't care. Will never visit majestic again. We wanted colonial for kids.
Reviewed on May 16, 2026
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! (1,737 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! (4,854 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
I really liked being close to the beach. I didn't like having a view of a construction site from the balcony.
Reviewed on May 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
Start your search for cheap flights to Caribbean on Orbitz. Orbitz is where you will discover guaranteed low prices on Caribbean flights, as well as all of the following conveniences:
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Low Prices Guaranteed on Flights to Caribbean
Orbitz offers large discounts on a wide range of Caribbean flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Caribbean while taking advantage of the lowest fares around.
Customer Care When You Need It
Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Caribbean to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.
Loyalty Program Participation Opportunities
Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Caribbean. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.
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.