$42 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $42 One Way, $101 Round Trip
$101 return flights and $42 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
$101 Roundtrip, found 19 hours ago
$101
Roundtrip
found 19 hours ago
BOS
Boston
SJU
San Juan
$110 Roundtrip, found 4 hours ago
$110
Roundtrip
found 4 hours ago
JFK
New York
SJU
San Juan
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
JFK
New York
SJU
San Juan
$185 Roundtrip, found 6 hours ago
$185
Roundtrip
found 6 hours ago
BOS
Boston
POS
Trinidad
$235 Roundtrip, found 1 hour ago
$235
Roundtrip
found 1 hour ago
JFK
New York
AUA
Oranjestad
$245 Roundtrip, found 3 days ago
$245
Roundtrip
found 3 days ago
BOS
Boston
SDQ
Santo Domingo
$258 Roundtrip, found 5 days ago
$258
Roundtrip
found 5 days ago
BOS
Boston
AUA
Oranjestad
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
JFK
New York
PUJ
Punta Cana
$267 Roundtrip, found 15 hours ago
$267
Roundtrip
found 15 hours ago
JFK
New York
SDQ
Santo Domingo
$271 Roundtrip, found 15 hours ago
$271
Roundtrip
found 15 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | San Juan | December 12 to December 17 | $200 |
| JFK | San Juan | December 14 to December 16 | $201 |
| EWR | Nassau | December 14 to December 20 | $342 |
| JFK | Punta Cana | December 12 to December 19 | $346 |
| JFK | Nassau | December 13 to December 16 | $373 |
| EWR | Santo Domingo | December 13 to December 23 | $390 |
| JFK | Santo Domingo | December 13 to December 23 | $390 |
| LGA | Piarco | December 12 to December 15 | $396 |
| LGA | Santiago de los Caballeros | December 13 to January 17 | $397 |
| JFK | Montego Bay | December 14 to December 16 | $410 |
| JFK | Santiago de los Caballeros | December 12 to December 15 | $462 |
| JFK | West End | December 14 to December 21 | $542 |
| JFK | West End | December 14 to December 21 | $542 |
| EWR | Kingston | December 12 to December 17 | $577 |
| JFK | Kingston | December 12 to December 17 | $578 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
Paradise Island Drive Paradise Island New Providence
$349 nightly
The price is $376 total per night from Dec 14 to Dec 15
$376 total
Dec 14 - Dec 15
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 ...
8.2/10 Very Good! (2,000 reviews)
The room was verry clean and the staff was fantastic! Really happy with my stay. Affordable no frills and get to take advantage of atlantis resort.
Reviewed on Dec 1, 2025
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $160 total per night from Jan 4 to Jan 5
$160 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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 (1,978 reviews)
Great service at the counter but the AC in Room #222 was loud. I asked to switch my room but they said that they are fully booked. I can understand that and I know that the employee would give me one if they had it. They were trying. So I gave a 4-star instead if a usual 3-star for malfunctioning ...
Reviewed on Dec 4, 2025
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
$293 nightly
The price is $323 total per night from Dec 8 to Dec 9
$323 total
Dec 8 - Dec 9
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 ...
7.4/10 Good! (1,994 reviews)
What an absolute amazing experience! I highly recommend this resort due to ALL of the amenities. The staff members went above and beyond. Not only did they all provide superlative service, they were very personable, professional and kind. The grounds were extremely well maintained. The food AND drinks ...
Reviewed on Nov 30, 2025
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Meridian Inn
Dover St. Lawrence Gap Christ Church
$71 nightly
The price is $83 total per night from Dec 16 to Dec 17
$83 total
Dec 16 - Dec 17
Total with taxes and fees
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! (829 reviews)
As mentioned by others, the staff was excellent, easy to speak with, unpretentious. Looking for a quiet getaway with a beach sans crowd steps away to public beach access, eateries and small grocery store within walking distance, then Meridian is the place.
Reviewed on Nov 30, 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
$290 nightly
The price is $303 total per night from Dec 15 to Dec 16
$303 total
Dec 15 - Dec 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 ...
8.8/10 Excellent! (1,500 reviews)
Clean room, a little bit old bathroom
Reviewed on Dec 5, 2025
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
$252 nightly
The price is $284 total per night from Dec 17 to Dec 18
$284 total
Dec 17 - Dec 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. ...
9.4/10 Exceptional! (1,014 reviews)
I really liked staying at Amsterdam Manor Beach Resort. The resort is cozy and quiet. We don't have small kids, and I didn't feel like having little kids running and splashing around nonstop. Our two-bedroom suite was absolutely fantastic, with an ocean view and a balcony with chairs and an umbrella. ...
Reviewed on Dec 3, 2025
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$463 nightly
The price is $524 total per night from Dec 16 to Dec 17
$524 total
Dec 16 - Dec 17
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! (1,001 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
$262 nightly
The price is $296 total per night from Dec 17 to Dec 18
$296 total
Dec 17 - Dec 18
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. ...
8.8/10 Excellent! (2,267 reviews)
Excellent spot if you don't want to eat all of your meals in restaurants. Easy walking distance to an excellent grocery store and enough of a kitchen to prepare meals. The three pools offer a lot of options and it is a short walk to an excellent sandy beach.
Reviewed on Dec 2, 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
$305 nightly
The price is $333 total per night from Dec 10 to Dec 11
$333 total
Dec 10 - Dec 11
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 ...
8.8/10 Excellent! (1,005 reviews)
Excellent location; walkable to everything imaginable. The staff at the Patio restaurant were great. The character of the hotel was quaint and aligned with its boutique nature. If you want to avoid the commercial nature of big chain hotels, this is a good one.
Reviewed on Dec 2, 2025
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$363 nightly
The price is $398 total per night from Dec 8 to Dec 9
$398 total
Dec 8 - Dec 9
Total with taxes and fees
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! (2,062 reviews)
Clean and nice staff
Reviewed on Dec 3, 2025
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $217 total per night from Dec 21 to Dec 22
$217 total
Dec 21 - Dec 22
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! (1,346 reviews)
We spent three nights here and it was perfect. The hotel is gorgeous, and the rooftop terrace—with its hot tub—was the pièce de résistance. The views of El Morro were absolutely incredible. Breakfast isn’t your standard, forgettable buffet; there’s a full menu with several options, and everything ...
Reviewed on Dec 4, 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! (1,425 reviews)
Another great stay at Atlantis. 4th time for my wife and I. Kids really enjoyed it this time around as they were older and couldn’t stay out of water park. First time at The Reef and room was good. Enjoyed being able to do breakfast and lunch in house. Only recommendation is rooms are too dark and ...
Reviewed on Dec 2, 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
$444 nightly
The price is $568 total per night from Jan 4 to Jan 5
$568 total
Jan 4 - Jan 5, 2026
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 ...
8/10 Very Good! (5,416 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
Good for a quick getaway.
Reviewed on Dec 3, 2025
Majestic Colonial Punta Cana - All Inclusive
Carretera El Macao Punta Cana La Altagracia
$416 nightly
The price is $416 total per night from Dec 10 to Dec 11
$416 total
Dec 10 - Dec 11
Total with taxes and fees
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)
Excellent service as always
Reviewed on Dec 7, 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! (1,963 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
$424 nightly
The price is $424 total per night from Dec 9 to Dec 10
$424 total
Dec 9 - Dec 10
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 restaurant in our reviews. ...
8.8/10 Excellent! (4,570 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
Great vacation
Reviewed on Dec 6, 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?
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Compact
Ford Focus or similar
Midsize
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SUV
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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.