$44 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $44 One Way, $95 Round Trip
$95 return flights and $44 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
$95 Roundtrip, just found
$95
Roundtrip
just found
JFK
New York
SJU
San Juan
$252 Roundtrip, just found
$252
Roundtrip
just found
MIA
Miami
SDQ
Santo Domingo
$263 Roundtrip, just found
$263
Roundtrip
just found
EWR
New York
SJU
San Juan
$266 Roundtrip, just found
$266
Roundtrip
just found
MIA
Miami
PUJ
Punta Cana
$274 Roundtrip, found 2 hours ago
$274
Roundtrip
found 2 hours ago
MIA
Miami
POS
Trinidad
$280 Roundtrip, found 4 hours ago
$280
Roundtrip
found 4 hours ago
MIA
Miami
NAS
Nassau
$293 Roundtrip, just found
$293
Roundtrip
just found
JFK
New York
MBJ
Montego Bay
$318 Roundtrip, just found
$318
Roundtrip
just found
JFK
New York
PUJ
Punta Cana
$323 Roundtrip, found 11 hours ago
$323
Roundtrip
found 11 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LGA | Nassau | August 29 to September 2 | $422 |
| JFK | San Juan | August 29 to September 5 | $431 |
| EWR | Piarco | August 28 to September 5 | $453 |
| EWR | San Juan | August 29 to September 2 | $472 |
| EWR | Montego Bay | August 29 to September 12 | $479 |
| JFK | Nassau | August 29 to September 4 | $504 |
| EWR | Kingston | August 30 to September 3 | $507 |
| JFK | Punta Cana | August 30 to September 4 | $540 |
| LGA | Santiago de los Caballeros | August 30 to September 5 | $573 |
| JFK | Santo Domingo | August 30 to September 15 | $580 |
| JFK | Santiago de los Caballeros | August 30 to September 8 | $583 |
| JFK | Piarco | August 30 to September 9 | $600 |
| JFK | Kingston | August 30 to September 6 | $646 |
| JFK | Oranjestad | August 29 to September 11 | $648 |
| EWR | Santo Domingo | August 30 to September 9 | $657 |
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 $348 total per night from Sep 1 to Sep 2
$348 total
per night
Sep 1 - Sep 2
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! (2,416 reviews)
"Had a great few days stay here - the free breakfast was pretty good and had a lovely variety (waffles, cereal, eggs, protein, pastries, juices, coffee etc) Also loved having free daily access to Atlantis during our stay :) would definitely come back!"
Reviewed on Aug 26, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
The price is $140 total per night from Aug 30 to Aug 31
$140 total
per night
Aug 30 - Aug 31
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 (2,429 reviews)
"Clean Greta location. Quite. Great spot to stay at."
Reviewed on Aug 25, 2026
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
The price is $349 total per night from Aug 27 to Aug 28
$349 total
per night
Aug 27 - Aug 28
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 ...
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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 $171 total per night from Sep 13 to Sep 14
$171 total
per night
Sep 13 - Sep 14
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 ...
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
The price is $400 total per night from Aug 30 to Aug 31
$400 total
per night
Aug 30 - Aug 31
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! (1,010 reviews)
"We loved how spacious, clean, and convenient our room was. It was near the pool, we had a terrace with ocean view, and it was just across from one of the best beaches! Couldn’t have asked for a better location. The pool was small but not crowded and the kids could enjoy it. We wished there was a ..."
Reviewed on Aug 25, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
The price is $612 total per night from Aug 29 to Aug 30
$612 total
per night
Aug 29 - Aug 30
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! (1,001 reviews)
"I loved it and would consider it again in the future"
Reviewed on Aug 26, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
The price is $344 total per night from Sep 25 to Sep 26
$344 total
per night
Sep 25 - Sep 26
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. ...
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 $270 total per night from Sep 7 to Sep 8
$270 total
per night
Sep 7 - Sep 8
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)
"Great staff and great hotel, the location is the best!"
Reviewed on Aug 24, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
The price is $236 total per night from Sep 7 to Sep 8
$236 total
per night
Sep 7 - Sep 8
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 ...
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
The price is $207 total per night from Sep 20 to Sep 21
$207 total
per night
Sep 20 - Sep 21
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! (1,880 reviews)
"Unique"
Reviewed on Aug 26, 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 ...
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 $287 total per night from Aug 31 to Sep 1
$287 total
per night
Aug 31 - Sep 1
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! (1,531 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
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! (4,920 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"We are definitely coming back next year."
Reviewed on Aug 26, 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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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.