$59 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $59 One Way, $118 Round Trip
$118 return flights and $59 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.
MIA
Miami
SJU
San Juan
$118 Roundtrip, just found
$118
Roundtrip
just found
EWR
New York
SJU
San Juan
$243 Roundtrip, found 2 days ago
$243
Roundtrip
found 2 days ago
MIA
Miami
POS
Trinidad
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
MIA
Miami
NAS
Nassau
$292 Roundtrip, just found
$292
Roundtrip
just found
MIA
Miami
SDQ
Santo Domingo
$292 Roundtrip, found 2 days ago
$292
Roundtrip
found 2 days ago
EWR
New York
SJU
San Juan
$295 Roundtrip, found 4 days ago
$295
Roundtrip
found 4 days ago
MIA
Miami
PUJ
Punta Cana
$296 Roundtrip, just found
$296
Roundtrip
just found
JFK
New York
SJU
San Juan
$296 Roundtrip, found 1 hour ago
$296
Roundtrip
found 1 hour ago
EWR
New York
AUA
Oranjestad
$308 Roundtrip, found 5 days ago
$308
Roundtrip
found 5 days ago
EWR
New York
SJU
San Juan
$312 Roundtrip, found 5 days ago
$312
Roundtrip
found 5 days ago
EWR
New York
AUA
Oranjestad
$313 Roundtrip, found 5 days ago
$313
Roundtrip
found 5 days ago
EWR
New York
STI
Santiago de los Caballeros
$318 Roundtrip, just found
$318
Roundtrip
just found
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Montego Bay | October 18 to October 30 | $358 |
| EWR | San Juan | October 18 to October 23 | $363 |
| EWR | San Juan | October 18 to October 23 | $363 |
| JFK | Oranjestad | October 17 to October 22 | $428 |
| JFK | Santo Domingo | October 18 to October 25 | $431 |
| JFK | Santo Domingo | October 18 to October 25 | $431 |
| EWR | Punta Cana | October 17 to October 20 | $447 |
| JFK | Santiago de los Caballeros | October 18 to November 1 | $478 |
| JFK | Santiago de los Caballeros | October 18 to November 1 | $478 |
| JFK | Punta Cana | October 17 to October 20 | $480 |
| EWR | Nassau | October 16 to October 24 | $499 |
| EWR | Santiago de los Caballeros | October 17 to November 6 | $507 |
| EWR | Piarco | October 16 to October 26 | $516 |
| JFK | Piarco | October 18 to October 24 | $540 |
| EWR | Kingston | October 17 to October 20 | $595 |
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 25 to Oct 26
$366 total
Oct 25 - Oct 26
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
$92 nightly
The price is $101 total per night from Oct 13 to Oct 14
$101 total
Oct 13 - Oct 14
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. ...
6.4/10 (2,471 reviews)
"I booked a 6.4 room. I shouldn’t have been surprised but the hair on the toilet and hair in the bedsheets was extra special"
Reviewed on Oct 11, 2026
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! (2,466 reviews)
"Breezes is on beach, hotel was nice but does need updating,( work is being done at moment, they have retiled pools, hung hammocks on ground floor) Rooms have dark wood furniture so makes room seem dark, need to add kettles, Fridge and sofas in room to make it feel cosy, Staff are happy and friendly ..."
Reviewed on Oct 11, 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
$161 nightly
The price is $169 total per night from Oct 14 to Oct 15
$169 total
Oct 14 - Oct 15
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! (2,106 reviews)
"They pull in front of a room. not working. We had to walk all the way down to the main building to swimming pool."
Reviewed on Oct 11, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
$303 nightly
The price is $340 total per night from Oct 18 to Oct 19
$340 total
Oct 18 - Oct 19
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! (1,001 reviews)
"We had a lovely stay at Amsterdam Manor! The hotel was clean, quiet, and conveniently located close to the beach. The staff were friendly and welcoming. A wonderful place for a relaxing vacation!"
Reviewed on Oct 9, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$541 nightly
The price is $612 total per night from Oct 13 to Oct 14
$612 total
Oct 13 - Oct 14
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! (1,002 reviews)
"Great stay. Property was beautiful and clean"
Reviewed on Oct 11, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
$369 nightly
The price is $428 total per night from Nov 10 to Nov 11
$428 total
Nov 10 - Nov 11
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! (1,815 reviews)
"The hotel itself was okay. Pools were nice. The rooms were not clean at all. We had a roach -a big one . We went down to front desk - it was 11 pm. We were tired from our night out and offered little help. They said cleaning crew was unavailable. No apology at all. We had to move are room from 1st ..."
Reviewed on Oct 8, 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
$392 nightly
The price is $427 total per night from Oct 13 to Oct 14
$427 total
Oct 13 - Oct 14
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 ...
9.4/10 Exceptional! (1,005 reviews)
"The hotel staff were always around to help answer any questions or concerns. The staff worked very hard to make our vacation very relaxing and enjoyable. The free wine and cheese hour from 5pm until 6Pm was an excellent way to relax and meet people staying at the hotel. The free coffee and tea service ..."
Reviewed on Oct 10, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$270 nightly
The price is $296 total per night from Oct 13 to Oct 14
$296 total
Oct 13 - Oct 14
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! (3,107 reviews)
"Great location as it is on both a main road and the beach. The restaurant was not open for breakfast everyday, so that was a negative for us."
Reviewed on Oct 11, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $167 total per night from Oct 18 to Oct 19
$167 total
Oct 18 - Oct 19
Total with taxes and fees
Book a stay at this business-friendly hotel in San Juan. Enjoy free WiFi, a casino, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
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 ...
9/10 Wonderful! (1,716 reviews)
"Welcoming staff, clean place, breathtaking landscape and the beach is clean."
Reviewed on Oct 9, 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
$218 nightly
The price is $279 total per night from Oct 21 to Oct 22
$279 total
Oct 21 - Oct 22
Total with taxes and fees
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bavaro Beach and Downtown ...
8/10 Very Good! (6,219 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"When we arrived we were told our room was ready, we got to our room we had two men staying in our room unauthorized. We told the hotel, they just laughed and kept sending us to different staff. Management refused to speak to us. The would not give us a refund or an upgrade. We booked two rooms, they ..."
Reviewed on Oct 11, 2026
Majestic Colonial Punta Cana - All Inclusive
Carretera El Macao Punta Cana La Altagracia
$306 nightly
The price is $306 total per night from Nov 8 to Nov 9
$306 total
Nov 8 - Nov 9
Total with taxes and fees
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Macao Beach and Arena Gorda ...
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! (1,450 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
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
Snag some “suite” deals when you add cheap hotel rooms to Caribbean flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.
Budget Prices, Luxury Life
Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Caribbean.
Fun for All
While shopping Orbitz sales on Caribbean flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.
Non-Stop or Stop and Visit
Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Caribbean flights, you will always find the best air travel prices at Orbitz.
All in One
Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Caribbean. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.
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.