$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, just found
$118
Roundtrip
just found
EWR
New York
SJU
San Juan
$258 Roundtrip, found 13 hours ago
$258
Roundtrip
found 13 hours ago
EWR
New York
SDQ
Santo Domingo
$270 Roundtrip, found 4 days ago
$270
Roundtrip
found 4 days ago
MIA
Miami
POS
Trinidad
$280 Roundtrip, found 1 day ago
$280
Roundtrip
found 1 day ago
MIA
Miami
PUJ
Punta Cana
$283 Roundtrip, found 2 hours ago
$283
Roundtrip
found 2 hours ago
MIA
Miami
SDQ
Santo Domingo
$289 Roundtrip, found 2 hours ago
$289
Roundtrip
found 2 hours ago
MIA
Miami
NAS
Nassau
$291 Roundtrip, found 18 hours ago
$291
Roundtrip
found 18 hours ago
EWR
New York
PUJ
Punta Cana
$303 Roundtrip, just found
$303
Roundtrip
just found
JFK
New York
NAS
Nassau
$306 Roundtrip, just found
$306
Roundtrip
just found
EWR
New York
AUA
Oranjestad
$308 Roundtrip, just found
$308
Roundtrip
just found
EWR
New York
SJU
San Juan
$312 Roundtrip, found 13 hours ago
$312
Roundtrip
found 13 hours 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* |
|---|---|---|---|
| JFK | Montego Bay | October 3 to October 7 | $426 |
| JFK | Montego Bay | October 3 to October 7 | $426 |
| EWR | Nassau | October 4 to October 9 | $429 |
| JFK | Oranjestad | October 4 to October 8 | $431 |
| JFK | Oranjestad | October 4 to October 8 | $431 |
| JFK | San Juan | October 2 to October 30 | $436 |
| JFK | Santo Domingo | October 4 to October 7 | $487 |
| JFK | Santiago de los Caballeros | October 2 to October 9 | $528 |
| JFK | Santiago de los Caballeros | October 2 to October 9 | $528 |
| JFK | Piarco | October 2 to October 16 | $540 |
| JFK | Piarco | October 2 to October 16 | $540 |
| LGA | Kingston | October 3 to October 13 | $585 |
| JFK | Kingston | October 2 to October 5 | $587 |
| EWR | Kingston | October 3 to October 13 | $591 |
| JFK | Nassau | October 3 to October 20 | $761 |
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
$359 nightly
The price is $396 total per night from Oct 4 to Oct 5
$396 total
Oct 4 - Oct 5
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 30 to Oct 31
$113 total
Oct 30 - Oct 31
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! (2,458 reviews)
"We cannot say enough about how beautiful and well-maintained the grounds were. We were happy with the availability of so many comfortable chairs and sheltered areas to relax on the beach and loved the hammocks multiple sitting areas around the grounds. There were some signs of wear and tear as would ..."
Reviewed on Sep 30, 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
$168 nightly
The price is $176 total per night from Oct 6 to Oct 7
$176 total
Oct 6 - Oct 7
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! (2,076 reviews)
"The only problem was American visitors who were not following the rules at the pool. They were aggressive, rude and used very foul language with me when I politely asked them to turn off their boom box, stop throwing things around and respect other people at the pool. I got absolutely no support ..."
Reviewed on Sep 30, 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 Oct 18 to Oct 19
$350 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. ...
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$534 nightly
The price is $604 total per night from Oct 1 to Oct 2
$604 total
Oct 1 - Oct 2
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! (1,000 reviews)
"Liked how it was located between Palm beach and Eagle beach. Walkable each way. Dislikes: Room generally clean but I found an old contact lens on the floor in the bathroom One or the knives had breadcrumbs on it I booked my room to be ocean view and my view was the vacation center; basically resort ..."
Reviewed on Sep 29, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
$332 nightly
The price is $385 total per night from Oct 30 to Oct 31
$385 total
Oct 30 - Oct 31
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. ...
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
$419 nightly
The price is $457 total per night from Oct 1 to Oct 2
$457 total
Oct 1 - Oct 2
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 Oct 4 to Oct 5
$300 total
Oct 4 - Oct 5
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! (3,078 reviews)
"The hotel staff were amazing shoutout to Ashlee, Randy, Anwar, Noel door staff. We went for my sisters birthday & everything was great until at 6:30 pm we received a noise complaint from British airways steward for singing happy birthday. The British airway employee escalated the complaint & in turn ..."
Reviewed on Sep 30, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $180 total per night from Oct 11 to Oct 12
$180 total
Oct 11 - Oct 12
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! (1,949 reviews)
"Excellent location, excellent and friendly staff."
Reviewed on Sep 27, 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
$218 nightly
The price is $279 total per night from Oct 4 to Oct 5
$279 total
Oct 4 - Oct 5
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! (1,455 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. ...
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.
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Caribbean
Start your search for cheap flights to Caribbean on Orbitz. Orbitz is where you will discover guaranteed low prices on Caribbean flights, as well as all of the following conveniences:
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Low Prices Guaranteed on Flights to Caribbean
Orbitz offers large discounts on a wide range of Caribbean flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Caribbean while taking advantage of the lowest fares around.
Customer Care When You Need It
Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Caribbean to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.
Loyalty Program Participation Opportunities
Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Caribbean. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.
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.