$106 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $106 One Way, $232 Round Trip
$232 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
$232 Roundtrip, found 7 hours ago
$232
Roundtrip
found 7 hours ago
EWR
New York
SJU
San Juan
$246 Roundtrip, found 4 hours ago
$246
Roundtrip
found 4 hours ago
BOS
Boston
SJU
San Juan
$296 Roundtrip, found 1 day ago
$296
Roundtrip
found 1 day ago
JFK
New York
NAS
Nassau
$313 Roundtrip, found 4 hours ago
$313
Roundtrip
found 4 hours ago
EWR
New York
PUJ
Punta Cana
$315 Roundtrip, just found
$315
Roundtrip
just found
EWR
New York
SDQ
Santo Domingo
$315 Roundtrip, just found
$315
Roundtrip
just found
JFK
New York
SDQ
Santo Domingo
$322 Roundtrip, found 4 hours ago
$322
Roundtrip
found 4 hours ago
JFK
New York
MBJ
Montego Bay
$328 Roundtrip, found 15 hours ago
$328
Roundtrip
found 15 hours ago
BOS
Boston
SDQ
Santo Domingo
$329 Roundtrip, found 5 days ago
$329
Roundtrip
found 5 days ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Montego Bay | August 15 to September 11 | $443 |
| EWR | Piarco | August 14 to September 8 | $464 |
| EWR | Piarco | August 14 to September 8 | $464 |
| JFK | San Juan | August 15 to August 22 | $466 |
| LGA | Oranjestad | August 16 to August 22 | $576 |
| LGA | Santiago de los Caballeros | August 15 to August 30 | $626 |
| JFK | Santiago de los Caballeros | August 14 to August 31 | $639 |
| JFK | Punta Cana | August 16 to August 21 | $658 |
| JFK | Punta Cana | August 16 to August 21 | $658 |
| JFK | Piarco | August 15 to August 19 | $698 |
| JFK | Nassau | August 15 to August 19 | $745 |
| EWR | Santo Domingo | August 15 to September 2 | $767 |
| JFK | Oranjestad | August 16 to August 22 | $839 |
| EWR | Punta Cana | August 16 to August 22 | $890 |
| EWR | Santiago de los Caballeros | August 15 to September 2 | $979 |
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 16 to Aug 17
$383 total
per night
Aug 16 - Aug 17
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! (2,382 reviews)
"The staff are hospitable and helpful The public spaces were clean and well kept."
Reviewed on Aug 13, 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. ...
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
The price is $342 total per night from Aug 18 to Aug 19
$342 total
per night
Aug 18 - Aug 19
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! (2,395 reviews)
"We had an amazing vacation very comfortable. Food was good and Staff was incredible."
Reviewed on Aug 13, 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
$160 nightly
The price is $168 total per night from Sep 9 to Sep 10
$168 total
Sep 9 - Sep 10
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! (1,949 reviews)
"The staff was very friendly and accommodating The rooms were kept clean The views were lovely I will definitely be coming back and referring friends"
Reviewed on Aug 12, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
$320 nightly
The price is $360 total per night from Aug 23 to Aug 24
$360 total
Aug 23 - Aug 24
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! (1,006 reviews)
"Great location, just in front the beach. Amenities are just perfect for families, couples or solo travelers. Pool is small but to be honest I think you don't need it. Restaurante and bar are good places to chill, see the sunset, or have fun. My only complaint is that you need to go to the restaurant ..."
Reviewed on Aug 10, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$541 nightly
The price is $612 total per night from Aug 14 to Aug 15
$612 total
Aug 14 - Aug 15
Total with taxes and fees
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! (1,001 reviews)
"My Wife and I were very pleased with our stay ( 7/28 to 8/4)…Staff was mostly excellent …Concierge and Pool Maintainer Leo were excellent and very friendly…The one complaint I have about personnel is the Lady that works in the Market; she follows you around the small store as if you’re going to steal ..."
Reviewed on Aug 12, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
$288 nightly
The price is $335 total per night from Sep 12 to Sep 13
$335 total
Sep 12 - Sep 13
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! (1,866 reviews)
"Great location, clean room, full kitchen with a full size refrigerator, free parking, free washer/dryer- just bring detergent/dryer sheets, fast elevator, excellent air conditioning was greatly appreciated, towels for the beach and pool were provided. Superfoods grocery store is nearby- we went daily, ..."
Reviewed on Aug 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
The price is $222 total per night from Sep 1 to Sep 2
$222 total
per night
Sep 1 - Sep 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 ...
9.2/10 Wonderful! (1,002 reviews)
"Great stay ! Everything was smooth"
Reviewed on Aug 13, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
The price is $260 total per night from Sep 8 to Sep 9
$260 total
per night
Sep 8 - Sep 9
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! (2,893 reviews)
"Belle hôtel. Le personnel est courtoie. Propre et quelques activités. Le seul problème rencontrer, est qu'ils nous envoyaient des messages avant notre arrivée sur plusieurs jours, pour faire des demandes aux concièrge. Je leur demandais s'il était possible de pouvoir laisser nos bagages à la réception ..."
Reviewed on Aug 12, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
The price is $226 total per night from Aug 30 to Aug 31
$226 total
per night
Aug 30 - Aug 31
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! (1,852 reviews)
"La vista hermosa, limpio, servicio excelente."
Reviewed on Aug 11, 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! (1,641 reviews)
"jj"
Reviewed on Aug 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.
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Carretera Bávaro Km. 1 Punta Cana La Altagracia
The price is $280 total per night from Sep 11 to Sep 12
$280 total
per night
Sep 11 - Sep 12
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 ...
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! (4,913 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"Staff was rude with poor customer service. If you called customer service they were rude and did not respond quickly (over 24 hours) for a blanket and tv that didn’t work took 48 hours"
Reviewed on Aug 13, 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.
Need a Car For After Your Flight?
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Caribbean
If you are looking for affordable flights to Caribbean, look no further. Orbitz offers discounted rates to many destinations.
Bargain flights to Caribbean now available
As you review your budget and travel plans, consider the low fares Orbitz offers on Caribbean flights. With Orbitz, booking flights to Caribbean is easy and the lowest prices are guaranteed.
Easy self-help service offered
Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Caribbean flights by visiting the Orbitz site or mobile application.
Orbitz looks after you
Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Caribbean flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.
Traveler profile updates
After booking your Caribbean flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings with Orbitz.
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.