$114 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $114 One Way, $252 Round Trip
$252 return flights and $114 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
EWR
New York
SJU
San Juan
$266 Roundtrip, found 4 hours ago
$266
Roundtrip
found 4 hours ago
EWR
New York
SJU
San Juan
$278 Roundtrip, found 3 days ago
$278
Roundtrip
found 3 days ago
EWR
New York
PUJ
Punta Cana
$283 Roundtrip, found 3 hours ago
$283
Roundtrip
found 3 hours ago
EWR
New York
SDQ
Santo Domingo
$283 Roundtrip, just found
$283
Roundtrip
just found
BOS
Boston
SJU
San Juan
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
EWR
New York
SJU
San Juan
$297 Roundtrip, just found
$297
Roundtrip
just found
EWR
New York
SJU
San Juan
$302 Roundtrip, found 2 hours ago
$302
Roundtrip
found 2 hours ago
JFK
New York
MBJ
Montego Bay
$318 Roundtrip, found 5 hours ago
$318
Roundtrip
found 5 hours ago
JFK
New York
STI
Santiago de los Caballeros
$320 Roundtrip, found 4 hours ago
$320
Roundtrip
found 4 hours ago
BOS
Boston
SDQ
Santo Domingo
$322 Roundtrip, found 6 days ago
$322
Roundtrip
found 6 days ago
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* |
|---|---|---|---|
| EWR | Nassau | September 5 to September 11 | $413 |
| EWR | Oranjestad | September 6 to September 10 | $429 |
| LGA | San Juan | September 5 to September 9 | $435 |
| EWR | Piarco | September 5 to September 8 | $453 |
| JFK | San Juan | September 5 to September 12 | $461 |
| JFK | Nassau | September 6 to September 9 | $469 |
| EWR | Santo Domingo | September 4 to October 11 | $506 |
| EWR | Santo Domingo | September 4 to October 11 | $506 |
| JFK | Montego Bay | September 6 to September 11 | $526 |
| JFK | Oranjestad | September 6 to September 11 | $553 |
| JFK | Santiago de los Caballeros | September 6 to September 25 | $563 |
| JFK | Punta Cana | September 6 to September 12 | $578 |
| JFK | Kingston | September 6 to September 11 | $624 |
| EWR | Santiago de los Caballeros | September 5 to September 9 | $632 |
| JFK | Piarco | September 5 to September 7 | $690 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
Paradise Island Drive Paradise Island New Providence
$355 nightly
The price is $383 total per night from Sep 2 to Sep 3
$383 total
Sep 2 - Sep 3
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 ...
8.4/10 Very Good! (2,430 reviews)
"Great"
Reviewed on Sep 1, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $140 total per night from Sep 2 to Sep 3
$140 total
Sep 2 - Sep 3
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
$314 nightly
The price is $349 total per night from Oct 2 to Oct 3
$349 total
Oct 2 - Oct 3
Total with taxes and fees
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 ...
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 $176 total per night from Sep 27 to Sep 28
$176 total
per night
Sep 27 - Sep 28
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! (1,989 reviews)
"We had an excellent stay. Everyone is extremely friendly and the property is great. Our only complaint is that we checked in on a Monday to leave on a Sunday (the property operates on a Saturday-Saturday or Sunday-Sunday schedule) and we were told with very little notice that we needed to vacate ..."
Reviewed on Aug 31, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
The price is $364 total per night from Sep 17 to Sep 18
$364 total
per night
Sep 17 - Sep 18
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! (1,002 reviews)
"This hotel was great. We stayed in the one bedroom suite. They pretty much thought of everything you could possibly need. If I had to nick pick I wish the bathroom light had a dimmer. It’s bright bright or nothing lol. Preferred to use the light from my phone when I went to the bathroom in the middle ..."
Reviewed on Sep 1, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
The price is $604 total per night from Oct 2 to Oct 3
$604 total
per night
Oct 2 - Oct 3
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
Fully refundableReserve now, pay when you stay
The price is $329 total per night from Oct 1 to Oct 2
$329 total
per night
Oct 1 - Oct 2
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! (1,869 reviews)
"Loved the pools and the short walk to Eagle beach !"
Reviewed on Aug 29, 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 $270 total per night from Sep 2 to Sep 3
$270 total
per night
Sep 2 - Sep 3
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)
"They should clean the building next door to improve the view."
Reviewed on Aug 31, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
The price is $241 total per night from Sep 26 to Sep 27
$241 total
per night
Sep 26 - Sep 27
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! (2,980 reviews)
"The only issue I had was for a vacation hotel, I had to go to smugglers to get a Bloody Mary for breakfast."
Reviewed on Sep 1, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
The price is $190 total per night from Sep 23 to Sep 24
$190 total
per night
Sep 23 - Sep 24
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! (1,899 reviews)
"N/a"
Reviewed on Sep 1, 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 ...
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 ...
8.2/10 Very Good! (6,080 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"I loved the room with 2 bedrooms and 3beds, the fridge was not in working condition, running out toilet paper very quickly"
Reviewed on Sep 1, 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! (1,531 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
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! (4,969 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"Una experiencia increíble y muy buena atención"
Reviewed on Sep 1, 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
Finding cheap flights to Caribbean is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Caribbean flights, but we also include some special extras to make booking a breeze. Just check out our:
Mobile Site and Apps
With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Caribbean through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Caribbean—even on the same day.
Pick and Choose or Book Full Vacation Packages
Don’t just be satisfied with great deals on Caribbean flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.
Rewards That Are Miles Better
Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Caribbean with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.
Great Deals Every Day
Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.
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.