$58 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $58 One Way, $107 Round Trip
$107 return flights and $58 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
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
EWR
New York
SJU
San Juan
$116 Roundtrip, found 1 hour ago
$116
Roundtrip
found 1 hour ago
JFK
New York
SJU
San Juan
$171 Roundtrip, found 2 hours ago
$171
Roundtrip
found 2 hours ago
JFK
New York
SJU
San Juan
$185 Roundtrip, found 14 hours ago
$185
Roundtrip
found 14 hours ago
EWR
New York
AUA
Oranjestad
$245 Roundtrip, just found
$245
Roundtrip
just found
EWR
New York
PUJ
Punta Cana
$245 Roundtrip, just found
$245
Roundtrip
just found
EWR
New York
SDQ
Santo Domingo
$245 Roundtrip, just found
$245
Roundtrip
just found
JFK
New York
PUJ
Punta Cana
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
JFK
New York
STI
Santiago de los Caballeros
$271 Roundtrip, found 18 hours ago
$271
Roundtrip
found 18 hours ago
JFK
New York
SDQ
Santo Domingo
$273 Roundtrip, found 2 hours ago
$273
Roundtrip
found 2 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | San Juan | December 7 to December 13 | $153 |
| JFK | San Juan | December 6 to December 9 | $170 |
| LGA | Santiago de los Caballeros | December 6 to December 13 | $287 |
| LGA | Piarco | December 5 to December 8 | $305 |
| EWR | Santo Domingo | December 7 to December 9 | $307 |
| JFK | Santo Domingo | December 6 to December 7 | $309 |
| JFK | Santiago de los Caballeros | December 6 to December 7 | $313 |
| JFK | Punta Cana | December 7 to December 10 | $316 |
| JFK | Punta Cana | December 7 to December 10 | $316 |
| EWR | Oranjestad | December 5 to December 9 | $331 |
| JFK | Nassau | December 5 to December 13 | $360 |
| JFK | Piarco | December 5 to December 10 | $381 |
| JFK | Montego Bay | December 7 to December 20 | $385 |
| JFK | Oranjestad | December 6 to December 13 | $389 |
| JFK | Kingston | December 6 to December 13 | $485 |
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 Dec 1 to Dec 2
$352 total
per night
Dec 1 - Dec 2
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 ...
8.2/10 Very Good! (2,000 reviews)
Staff were so friendly and helpful. The room was cleaned daily. It was great to have complimentary breakfast, especially since Paradise Island is an expensive destination.
Reviewed on Nov 23, 2025
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
The price is $186 total per night from Dec 1 to Dec 2
$186 total
per night
Dec 1 - Dec 2
Stay at this hotel in Carolina. Enjoy free WiFi, 2 restaurants, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
6/10 (1,963 reviews)
yes
Reviewed on Nov 22, 2025
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
The price is $323 total per night from Dec 1 to Dec 2
$323 total
per night
Dec 1 - Dec 2
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 ...
7.4/10 Good! (1,992 reviews)
N/a
Reviewed on Nov 25, 2025
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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 ...
8.4/10 Very Good! (827 reviews)
We love the staff.
Reviewed on Nov 21, 2025
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
The price is $167 total per night from Dec 15 to Dec 16
$167 total
per night
Dec 15 - Dec 16
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 ...
8.8/10 Excellent! (1,497 reviews)
Beach was amazing, our room was on the first floor facing the parking.. therfore did not really like that. Tried to change but they said no other availability. Restaurants are close by. Roads around the complex need some major repairs. We rented a car which made it easier to get around. Rooms were ...
Reviewed on Nov 29, 2025
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
The price is $243 total per night from Dec 7 to Dec 8
$243 total
per night
Dec 7 - Dec 8
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. ...
9.4/10 Exceptional! (1,007 reviews)
The beach is stunning. Eagle Beach is a beautiful spot as there aren’t any high rises on the beach.
Reviewed on Nov 23, 2025
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
The price is $524 total per night from Dec 16 to Dec 17
$524 total
per night
Dec 16 - Dec 17
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! (1,007 reviews)
Newly renovated rooms. Right on the beach. Staff wonderful
Reviewed on Nov 23, 2025
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
The price is $306 total per night from Dec 2 to Dec 3
$306 total
per night
Dec 2 - Dec 3
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. ...
8.8/10 Excellent! (2,291 reviews)
the hotel and room service was phenomenal! we had a great time and would absolutely recommend it to anybody looking to vacation and relax!
Reviewed on Nov 25, 2025
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 $333 total per night from Dec 1 to Dec 2
$333 total
per night
Dec 1 - Dec 2
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 ...
8.8/10 Excellent! (1,000 reviews)
The room was very clean staff was very friendly enjoyed my stay and will go back again 😊
Reviewed on Nov 15, 2025
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
The price is $372 total per night from Dec 14 to Dec 15
$372 total
per night
Dec 14 - Dec 15
Book a stay at this beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 8 restaurants. Our guests praise the helpful staff and the clean rooms in our ...
8.6/10 Excellent! (2,046 reviews)
What stood out was the architectural structure of the hotel and how clean it was upon arrival, from the hotel grounds, lobby, restaurants, hallways, and rooms.
Reviewed on Nov 21, 2025
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
The price is $207 total per night from Dec 16 to Dec 17
$207 total
per night
Dec 16 - Dec 17
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! (1,329 reviews)
Bay view room was spacious. Location was convenient for the cruise port and also for sightseeing.
Reviewed on Nov 29, 2025
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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 ...
8.8/10 Excellent! (1,434 reviews)
Amazing b
Reviewed on Nov 24, 2025
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 $333 total per night from Dec 5 to Dec 6
$333 total
per night
Dec 5 - Dec 6
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 ...
8/10 Very Good! (5,425 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
I love this resort. I definitely come back
Reviewed on Nov 27, 2025
Majestic Colonial Punta Cana - All Inclusive
Carretera El Macao Punta Cana La Altagracia
The price is $416 total per night from Dec 10 to Dec 11
$416 total
per night
Dec 10 - Dec 11
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. ...
8.8/10 Excellent! (6,376 reviews)
The giant pool, the well trained employees the service the quality of the food great Trainer at the gym beautiful beach Greatwater
Reviewed on Nov 25, 2025
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! (1,975 reviews)
Families like: Outdoor pools, free waterpark access, kids club, playground
Travelers say...
Pool was enjoyable and not crowded. Food excellent. Would spend a whole week there and i dont really like all inclusive hotels.
Reviewed on Nov 25, 2025
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Majestic Elegance Punta Cana - All Inclusive
Playa Bavaro - Punta Cana Punta Cana La Altagracia
The price is $424 total per night from Dec 9 to Dec 10
$424 total
per night
Dec 9 - Dec 10
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. ...
8.8/10 Excellent! (4,563 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
Good
Reviewed on Nov 24, 2025
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 or similar
Compact
Ford Focus or similar
Midsize
Toyota Corolla or similar
SUV
Jeep Compass or similar
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.