$58 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $58 One Way, $118 Round Trip
$118 return flights and $58 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, found 1 hour ago
$118
Roundtrip
found 1 hour ago
MIA
Miami
PUJ
Punta Cana
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
MIA
Miami
SDQ
Santo Domingo
$217 Roundtrip, just found
$217
Roundtrip
just found
EWR
New York
SJU
San Juan
$261 Roundtrip, found 1 day ago
$261
Roundtrip
found 1 day ago
MIA
Miami
POS
Trinidad
$280 Roundtrip, found 3 days ago
$280
Roundtrip
found 3 days ago
MIA
Miami
NAS
Nassau
$293 Roundtrip, just found
$293
Roundtrip
just found
EWR
New York
SJU
San Juan
$297 Roundtrip, found 4 hours ago
$297
Roundtrip
found 4 hours ago
EWR
New York
PUJ
Punta Cana
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
EWR
New York
SDQ
Santo Domingo
$303 Roundtrip, found 6 hours ago
$303
Roundtrip
found 6 hours ago
EWR
New York
AUA
Oranjestad
$304 Roundtrip, just found
$304
Roundtrip
just found
EWR
New York
SJU
San Juan
$306 Roundtrip, found 16 hours ago
$306
Roundtrip
found 16 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Nassau | September 19 to September 22 | $388 |
| JFK | Nassau | September 19 to September 22 | $388 |
| LGA | San Juan | September 20 to September 30 | $448 |
| LGA | Piarco | September 19 to September 24 | $488 |
| EWR | Punta Cana | September 20 to September 24 | $490 |
| JFK | Montego Bay | September 19 to September 30 | $516 |
| JFK | San Juan | September 19 to October 3 | $517 |
| JFK | Punta Cana | September 20 to September 25 | $549 |
| JFK | Santiago de los Caballeros | September 19 to October 3 | $568 |
| JFK | Santiago de los Caballeros | September 19 to October 3 | $568 |
| EWR | Kingston | September 19 to September 24 | $568 |
| JFK | Piarco | September 20 to September 21 | $572 |
| JFK | Kingston | September 20 to September 23 | $587 |
| JFK | Santo Domingo | September 19 to September 22 | $611 |
| JFK | Oranjestad | September 19 to October 2 | $648 |
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 6 to Oct 7
$366 total
Oct 6 - Oct 7
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
$127 nightly
The price is $138 total per night from Sep 18 to Sep 19
$138 total
Sep 18 - Sep 19
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! (2,449 reviews)
"Ok, so I gave it 5 stars, However there are a few things that can be improved upon. First, there is a "great need" for a serious remodel or updates! Wife and her first husband was here 26 years ago. When we got here, she told me that it still looks the same!!!!! Also there needs to be a snack or ..."
Reviewed on Sep 14, 2026
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 Sep 23 to Sep 24
$191 total
Sep 23 - Sep 24
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! (2,034 reviews)
"The property is older/dated, however, it is clean. The staff were friendly and helpful."
Reviewed on Sep 15, 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 Sep 24 to Sep 25
$340 total
Sep 24 - Sep 25
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)
"The Room and hotel is great but the restaurant"
Reviewed on Sep 13, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$534 nightly
The price is $604 total per night from Sep 18 to Sep 19
$604 total
Sep 18 - Sep 19
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)
"Staff was nice and helpful and the rooms were always clean"
Reviewed on Sep 17, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
$321 nightly
The price is $373 total per night from Oct 18 to Oct 19
$373 total
Oct 18 - Oct 19
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! (1,836 reviews)
"Rooms was comfortable and clean. Property was amazing. Staff was amazing as well. We will be back."
Reviewed on Sep 16, 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
$339 nightly
The price is $370 total per night from Oct 18 to Oct 19
$370 total
Oct 18 - Oct 19
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! (1,000 reviews)
"The beautiful building and historic structure"
Reviewed on Sep 13, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$231 nightly
The price is $253 total per night from Sep 18 to Sep 19
$253 total
Sep 18 - Sep 19
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! (3,044 reviews)
"During my stay the staff was super friendly and helpful. The room was clean to perfection and the overall atmosphere was welcoming."
Reviewed on Sep 17, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $201 total per night from Sep 27 to Sep 28
$201 total
Sep 27 - Sep 28
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 ...
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 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 ...
8.2/10 Very Good! (6,129 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"El resort es muy hermoso, tiene muchas actividades para todas las edades. La comida es regular, buffet mejores opciones que en los restaurantes a la carta. Playa muy limpia. El servicio es regular, muchos empleados que tienen mucha actitud como que no quisieran estar allí, atienden de mala gana."
Reviewed on Sep 17, 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! (1,475 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
The Royal at Atlantis
Paradise Beach Drive Paradise Island New Providence
Book a stay at this beach resort in Paradise Island. Enjoy free WiFi, 14 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Families like: Outdoor pools, free waterpark access, 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.
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Caribbean
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Free Fees
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Mix and Match
At Orbitz, we turned a great idea from the world of fashion into another way for you to save money. When you shop our low cost tickets on flights to any destination, don’t be afraid to mix and match different airlines for maximum savings on your Caribbean flights air ticket. Save more on air travel every day in every way at 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.