$59 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $59 One Way, $116 Round Trip
$116 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
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
MIA
Miami
SDQ
Santo Domingo
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
EWR
New York
SJU
San Juan
$268 Roundtrip, found 2 hours ago
$268
Roundtrip
found 2 hours ago
MIA
Miami
POS
Trinidad
$280 Roundtrip, found 5 hours ago
$280
Roundtrip
found 5 hours ago
EWR
New York
SJU
San Juan
$291 Roundtrip, found 11 hours ago
$291
Roundtrip
found 11 hours ago
MIA
Miami
NAS
Nassau
$293 Roundtrip, just found
$293
Roundtrip
just found
MIA
Miami
PUJ
Punta Cana
$295 Roundtrip, found 11 hours ago
$295
Roundtrip
found 11 hours ago
EWR
New York
PUJ
Punta Cana
$303 Roundtrip, just found
$303
Roundtrip
just found
EWR
New York
SDQ
Santo Domingo
$303 Roundtrip, just found
$303
Roundtrip
just found
EWR
New York
SJU
San Juan
$317 Roundtrip, found 1 hour ago
$317
Roundtrip
found 1 hour ago
EWR
New York
SJU
San Juan
$317 Roundtrip, just found
$317
Roundtrip
just found
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | Nassau | September 27 to October 4 | $360 |
| EWR | Montego Bay | September 26 to September 28 | $410 |
| JFK | Nassau | September 27 to October 4 | $411 |
| JFK | Punta Cana | September 27 to October 10 | $443 |
| JFK | San Juan | September 26 to October 6 | $471 |
| EWR | Punta Cana | September 26 to October 10 | $499 |
| EWR | San Juan | September 26 to October 6 | $507 |
| JFK | Montego Bay | September 26 to September 29 | $519 |
| JFK | Santiago de los Caballeros | September 27 to October 6 | $520 |
| EWR | Kingston | September 27 to October 1 | $535 |
| JFK | Piarco | September 26 to October 8 | $540 |
| JFK | Piarco | September 26 to October 8 | $540 |
| EWR | Santo Domingo | September 27 to October 9 | $575 |
| JFK | Oranjestad | September 26 to September 30 | $670 |
| EWR | Santiago de los Caballeros | September 26 to October 12 | $678 |
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
$348 nightly
The price is $383 total per night from Sep 27 to Sep 28
$383 total
Sep 27 - Sep 28
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 24 to Oct 25
$113 total
Oct 24 - Oct 25
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 (2,449 reviews)
"Esta aceptable"
Reviewed on Sep 23, 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 ...
Save an average of 15% on thousands of hotels when you're signed in
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
$183 nightly
The price is $191 total per night from Oct 12 to Oct 13
$191 total
Oct 12 - Oct 13
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! (2,058 reviews)
"It was central and very close by to everything. Staff were friendly , views were amazing ."
Reviewed on Sep 24, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
$312 nightly
The price is $350 total per night from Sep 26 to Sep 27
$350 total
Sep 26 - Sep 27
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! (1,003 reviews)
"Close enough we could catch the bus to just about anywhere we wanted to go, yet we could return to a quiet peaceful evening and watch sunsets from our balcony. Staff was amazing, helpful and so friendly. We are looking forward to staying again on next vacation."
Reviewed on Sep 23, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$534 nightly
The price is $604 total per night from Sep 26 to Sep 27
$604 total
Sep 26 - Sep 27
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
$319 nightly
The price is $369 total per night from Oct 25 to Oct 26
$369 total
Oct 25 - Oct 26
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! (1,826 reviews)
"Rooms are big! Pools are well maintained and the staff are so very friendly especially Ashton always ready to assist!"
Reviewed on Sep 21, 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
$352 nightly
The price is $384 total per night from Oct 22 to Oct 23
$384 total
Oct 22 - Oct 23
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 ...
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 Sep 25 to Sep 26
$300 total
Sep 25 - Sep 26
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! (3,064 reviews)
"I loved my stay here, staff is very friendly and everyone makes u feel safe and comfortable."
Reviewed on Sep 24, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $178 total per night from Oct 1 to Oct 2
$178 total
Oct 1 - Oct 2
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! (1,942 reviews)
"No restaurant, dirty and minimal pool furniture. No beach."
Reviewed on Sep 24, 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! (1,701 reviews)
"We were so impressed with our suite, we had so much space with a kitchen, dining room, living room, and everything was steps away, pools, beach, waterpark. We will definitely be back."
Reviewed on Sep 24, 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 1 to Oct 2
$279 total
Oct 1 - Oct 2
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 ...
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! (1,464 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
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! (5,130 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"Everything was amazing with the staff especially for kids. They have an amazing program for kids withdrawing keeping them occupied exciting for them. A lot of fun things for a little kids to do."
Reviewed on Sep 24, 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
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Stay on Budget, Earn Miles with Bargain Caribbean Flights
You can find amazing discount fares with Orbitz’s guaranteed low prices or take advantage of last-minute sales and special travel packages. You can also earn points towards your airline frequent flyer programs when you book qualified flights to Caribbean. That means you can rack up money-saving points and miles for future use while saving money now.
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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.