$39 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $39 One Way, $78 Round Trip
$78 return flights and $39 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.
FLL
Fort Lauderdale
SJU
San Juan
$78 Roundtrip, found 16 hours ago
$78
Roundtrip
found 16 hours ago
JFK
New York
SJU
San Juan
$232 Roundtrip, found 20 hours ago
$232
Roundtrip
found 20 hours ago
EWR
New York
SJU
San Juan
$246 Roundtrip, found 19 hours ago
$246
Roundtrip
found 19 hours ago
EWR
New York
SJU
San Juan
$252 Roundtrip, found 5 hours ago
$252
Roundtrip
found 5 hours ago
EWR
New York
SJU
San Juan
$256 Roundtrip, found 2 days ago
$256
Roundtrip
found 2 days ago
FLL
Fort Lauderdale
PUJ
Punta Cana
$290 Roundtrip, found 13 hours ago
$290
Roundtrip
found 13 hours ago
FLL
Fort Lauderdale
NAS
Nassau
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
EWR
New York
SJU
San Juan
$306 Roundtrip, found 1 day ago
$306
Roundtrip
found 1 day ago
EWR
New York
SDQ
Santo Domingo
$319 Roundtrip, found 23 hours ago
$319
Roundtrip
found 23 hours ago
FLL
Fort Lauderdale
POS
Trinidad
$323 Roundtrip, found 5 days ago
$323
Roundtrip
found 5 days ago
JFK
New York
NAS
Nassau
$331 Roundtrip, found 5 days ago
$331
Roundtrip
found 5 days ago
EWR
New York
PUJ
Punta Cana
$335 Roundtrip, just found
$335
Roundtrip
just found
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | July 19 to August 1 | $367 |
| EWR | San Juan | July 19 to July 29 | $377 |
| LGA | Oranjestad | July 18 to July 24 | $427 |
| JFK | Oranjestad | July 18 to July 22 | $445 |
| EWR | Piarco | July 17 to July 29 | $449 |
| EWR | Nassau | July 19 to July 22 | $492 |
| LGA | Montego Bay | July 18 to July 20 | $507 |
| JFK | Santiago de los Caballeros | July 18 to July 23 | $548 |
| JFK | Santiago de los Caballeros | July 18 to July 23 | $548 |
| EWR | Montego Bay | July 19 to August 14 | $562 |
| JFK | Piarco | July 17 to July 31 | $565 |
| JFK | Montego Bay | July 18 to July 21 | $577 |
| JFK | Punta Cana | July 17 to July 19 | $659 |
| JFK | Kingston | July 19 to July 29 | $671 |
| EWR | Santo Domingo | July 17 to July 26 | $732 |
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 2 to Aug 3
$383 total
per night
Aug 2 - Aug 3
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! (2,347 reviews)
"The property was very conveniently located.It was in pretty good shape.The staff was nice and helpful.The pool was pretty good and the restaurant was decent"
Reviewed on Jul 14, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
The price is $143 total per night from Jul 15 to Jul 16
$143 total
per night
Jul 15 - Jul 16
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 (2,403 reviews)
"I’ll start off with the positives. The STAFF are amazing and do their best. Very kind and helpful & you can tell. Location is great, everything walking distance. Air conditioner was great. Again, Love love love the staff & gift shop next door has detergent for laundry and pads for menstrual for cheap, ..."
Reviewed on Jul 14, 2026
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
The price is $352 total per night from Aug 8 to Aug 9
$352 total
per night
Aug 8 - Aug 9
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! (2,340 reviews)
"Resort staff was excellent!"
Reviewed on Jul 14, 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
The price is $249 total per night from Aug 4 to Aug 5
$249 total
per night
Aug 4 - Aug 5
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! (1,888 reviews)
"Excellent location, clean and very comfortable.!"
Reviewed on Jul 14, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
The price is $344 total per night from Jul 28 to Jul 29
$344 total
per night
Jul 28 - Jul 29
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! (1,011 reviews)
"L"
Reviewed on Jul 13, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
The price is $596 total per night from Aug 9 to Aug 10
$596 total
per night
Aug 9 - Aug 10
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! (1,015 reviews)
"It was amazing"
Reviewed on Jul 14, 2026
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
The price is $384 total per night from Jul 30 to Jul 31
$384 total
per night
Jul 30 - Jul 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! (1,935 reviews)
"We stayed 8 nights (7-2026) at the Eagle Aruba. The staff was friendly & the room was clean. We had a 1 bedroom suite with a kitchen on the 4th floor overlooking the waterfall pool. The room had a pull-out sofa sleeper as well as 2 double beds. The beds were very comfortable with plenty of pillows ..."
Reviewed on Jul 14, 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
The price is $221 total per night from Jul 15 to Jul 16
$221 total
per night
Jul 15 - Jul 16
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! (1,017 reviews)
"Love this property! Best hotel in the Old San Juan. Courteous staff, beautiful grounds, extremely clean and we loved the coffee / water bar on the 3rd floor with the terrace overlooking the city. They even upgraded us to a suite for no additional charge. We will be back!"
Reviewed on Jul 12, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
The price is $235 total per night from Aug 12 to Aug 13
$235 total
per night
Aug 12 - Aug 13
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! (2,768 reviews)
"Je n’ai pratiquement pas dormi durant tout mon séjour. Le réfrigérateur dans la chambre faisait beaucoup trop de bruit. De plus, votre site indiquait que la réservation incluait un « accès VIP », mais je n’ai bénéficié d’aucun avantage ou service correspondant à cette mention. J’ai trouvé le prix ..."
Reviewed on Jul 14, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
The price is $204 total per night from Jul 19 to Jul 20
$204 total
per night
Jul 19 - Jul 20
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! (1,787 reviews)
"Great place to stay!"
Reviewed on Jul 14, 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 ...
9/10 Wonderful! (1,572 reviews)
"Staff were great!"
Reviewed on Jul 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.
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Carretera Bávaro Km. 1 Punta Cana La Altagracia
The price is $362 total per night from Aug 9 to Aug 10
$362 total
per night
Aug 9 - Aug 10
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 ...
8.2/10 Very Good! (5,842 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"First off, this resort is massive! They have trolleys going around about every 5 mins which helped out with all the walking. We arrived 2 hrs early but was allowed to check in early. Right after checking in, we went to concierge to make reservations for the restaurants but they told us that every ..."
Reviewed on Jul 14, 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. ...
9/10 Wonderful! (6,396 reviews)
"Terrible food and place needed to be upgraded"
Reviewed on Jun 9, 2026
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! (1,635 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! (4,914 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"."
Reviewed on Jul 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 discount prices on flights to Caribbean then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking Caribbean flights easy and affordable.
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The Complete Package
Orbitz makes it stress-free to book Caribbean flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to Caribbean, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.
Low Price Guarantee
Booking your Caribbean flights with Orbitz guarantees low prices every day, all day—no matter when and where you book. You will always find the best deals available, coupled with extra great savings and discounts for all around great value.
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.