$99 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $99 One Way, $269 Round Trip
$269 return flights and $99 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.
EWR
New York
SJU
San Juan
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
BOS
Boston
SJU
San Juan
$291 Roundtrip, found 2 hours ago
$291
Roundtrip
found 2 hours ago
EWR
New York
SJU
San Juan
$299 Roundtrip, found 13 hours ago
$299
Roundtrip
found 13 hours ago
JFK
New York
AUA
Oranjestad
$303 Roundtrip, found 7 hours ago
$303
Roundtrip
found 7 hours ago
EWR
New York
PUJ
Punta Cana
$304 Roundtrip, found 1 hour ago
$304
Roundtrip
found 1 hour ago
EWR
New York
SDQ
Santo Domingo
$304 Roundtrip, just found
$304
Roundtrip
just found
JFK
New York
NAS
Nassau
$306 Roundtrip, found 16 hours ago
$306
Roundtrip
found 16 hours ago
JFK
New York
SDQ
Santo Domingo
$310 Roundtrip, found 2 hours ago
$310
Roundtrip
found 2 hours ago
EWR
New York
SJU
San Juan
$312 Roundtrip, just found
$312
Roundtrip
just found
EWR
New York
SJU
San Juan
$317 Roundtrip, found 2 hours ago
$317
Roundtrip
found 2 hours ago
JFK
New York
STI
Santiago de los Caballeros
$318 Roundtrip, found 1 hour ago
$318
Roundtrip
found 1 hour ago
BOS
Boston
SDQ
Santo Domingo
$326 Roundtrip, found 7 hours ago
$326
Roundtrip
found 7 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | San Juan | October 4 to October 10 | $362 |
| EWR | San Juan | October 4 to October 10 | $362 |
| JFK | Montego Bay | October 4 to October 7 | $426 |
| JFK | Punta Cana | October 4 to October 17 | $443 |
| JFK | San Juan | October 3 to October 17 | $461 |
| EWR | Montego Bay | October 3 to October 9 | $482 |
| JFK | Santo Domingo | October 4 to October 7 | $487 |
| EWR | Oranjestad | October 3 to October 6 | $492 |
| EWR | Oranjestad | October 3 to October 6 | $492 |
| JFK | Oranjestad | October 4 to October 14 | $498 |
| JFK | Piarco | October 4 to October 17 | $541 |
| LGA | Santiago de los Caballeros | October 3 to October 7 | $557 |
| JFK | Santiago de los Caballeros | October 4 to October 7 | $571 |
| JFK | Nassau | October 4 to October 10 | $649 |
| JFK | Kingston | October 4 to October 7 | $716 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
Paradise Island Drive Paradise Island New Providence
Fully refundable
$333 nightly
The price is $366 total per night from Oct 14 to Oct 15
$366 total
Oct 14 - Oct 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 ...
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $113 total per night from Oct 31 to Nov 1
$113 total
Oct 31 - Nov 1
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
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! (2,459 reviews)
"Clean grounds, clean rooms, friendly staff from top to bottom, and every single staff member contributes to the well-oiled machine they are running over there. Every staff member knows their duty, and they do their jobs very well. So many employees have become family to us over the years. They are ..."
Reviewed on Sep 30, 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
The price is $168 total per night from Oct 5 to Oct 6
$168 total
per night
Oct 5 - Oct 6
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! (2,078 reviews)
"Great location balcony amazing and rooms were well air conditioned"
Reviewed on Oct 1, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
The price is $350 total per night from Oct 18 to Oct 19
$350 total
per night
Oct 18 - Oct 19
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! (1,007 reviews)
"The room was very clean and the staff was attentive to all of my needs. Karen the housekeeping manager was so pleasant and welcoming. Julio at the front desk made sure that anything needed was provided. The food at Passions on the Beach and Horizon Lounge was so delicious. The distance from the hotel ..."
Reviewed on Oct 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 ...
8.8/10 Excellent! (1,000 reviews)
"Liked how it was located between Palm beach and Eagle beach. Walkable each way. Dislikes: Room generally clean but I found an old contact lens on the floor in the bathroom One or the knives had breadcrumbs on it I booked my room to be ocean view and my view was the vacation center; basically resort ..."
Reviewed on Sep 29, 2026
Save an average of 15% on thousands of hotels when you're signed in
Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
The price is $385 total per night from Oct 30 to Oct 31
$385 total
per night
Oct 30 - Oct 31
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! (1,818 reviews)
"Excelent"
Reviewed on Sep 30, 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
$419 nightly
The price is $457 total per night from Oct 4 to Oct 5
$457 total
Oct 4 - Oct 5
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 ...
9.2/10 Wonderful! (1,003 reviews)
"This hotel is amazing! Free coffee/tea in the morning, wine and cheese tasting in the evenings. The pool was closed while I was there, but they offered the pool at their sister hotel as well as a free beach pass is included to Isla Verde Beach! Staff were super friendly and we had a wonderful ..."
Reviewed on Sep 30, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$274 nightly
The price is $300 total per night from Oct 4 to Oct 5
$300 total
Oct 4 - Oct 5
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! (3,079 reviews)
"Fantastyczny hotel, fajne pokoje, świetna plaża i baseny dla dzieciaków i dorosłych. Obsługa pod każdym względem fenomenalna chcąca pomóc. Blisko sklepy, restauracje , port, wycieczki. Polecam !!!"
Reviewed on Oct 1, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $180 total per night from Oct 11 to Oct 12
$180 total
Oct 11 - Oct 12
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! (1,949 reviews)
"Excellent location, excellent and friendly staff."
Reviewed on Sep 27, 2026
Save an average of 15% on thousands of hotels when you're signed in
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 11 to Oct 12
$279 total
Oct 11 - Oct 12
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! (6,179 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"El hotel es hermoso. Demasiado amplio. Tenía muchas baras para beber pero las áreas de comida se concentra en una sola área (edificio) Usaban unos rociadores para echarle agua a las áreas verdes que olía mal. (Aguas negras) El búfet es amplio. Los restaurantes fue excelente. Fui a 4 y todos exelente. ..."
Reviewed on Oct 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! (1,455 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
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. Popular attractions Macao Beach and Arena Gorda ...
Families like: Outdoor pools, waterslide, kids club, playground
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
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.