$97 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $97 One Way, $252 Round Trip
$252 return flights and $97 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.
JFK
New York
SJU
San Juan
$252 Roundtrip, found 10 hours ago
$252
Roundtrip
found 10 hours ago
EWR
New York
SJU
San Juan
$256 Roundtrip, found 2 days ago
$256
Roundtrip
found 2 days ago
JFK
New York
SJU
San Juan
$257 Roundtrip, found 4 hours ago
$257
Roundtrip
found 4 hours ago
EWR
New York
SJU
San Juan
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
EWR
New York
SJU
San Juan
$275 Roundtrip, found 1 hour ago
$275
Roundtrip
found 1 hour ago
EWR
New York
SJU
San Juan
$301 Roundtrip, found 13 hours ago
$301
Roundtrip
found 13 hours ago
EWR
New York
PUJ
Punta Cana
$305 Roundtrip, found 5 hours ago
$305
Roundtrip
found 5 hours ago
EWR
New York
SDQ
Santo Domingo
$305 Roundtrip, just found
$305
Roundtrip
just found
JFK
New York
SJU
San Juan
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
JFK
New York
MBJ
Montego Bay
$318 Roundtrip, found 3 hours ago
$318
Roundtrip
found 3 hours ago
JFK
New York
PUJ
Punta Cana
$337 Roundtrip, just found
$337
Roundtrip
just found
JFK
New York
POS
Trinidad
$350 Roundtrip, found 20 hours ago
$350
Roundtrip
found 20 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | May 24 to May 29 | $337 |
| JFK | Nassau | May 24 to May 28 | $369 |
| EWR | Nassau | May 24 to May 28 | $369 |
| JFK | Montego Bay | May 22 to May 29 | $403 |
| JFK | Santiago de los Caballeros | May 24 to May 30 | $403 |
| JFK | Santiago de los Caballeros | May 24 to May 30 | $403 |
| EWR | Piarco | May 23 to May 30 | $410 |
| JFK | Santo Domingo | May 24 to May 29 | $410 |
| JFK | Kingston | May 24 to June 12 | $464 |
| JFK | Kingston | May 24 to June 12 | $464 |
| EWR | Oranjestad | May 24 to May 26 | $491 |
| EWR | Santo Domingo | May 22 to May 27 | $542 |
| JFK | Oranjestad | May 24 to May 29 | $553 |
| JFK | Punta Cana | May 24 to May 27 | $555 |
| EWR | San Juan | May 23 to May 26 | $591 |
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 $352 total per night from May 17 to May 18
$352 total
per night
May 17 - May 18
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! (2,241 reviews)
Clean rooms… just need to update the decor to match the Bahamas vibe
Reviewed on May 13, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
The price is $233 total per night from May 16 to May 17
$233 total
per night
May 16 - May 17
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. ...
6.2/10 (2,365 reviews)
Clean room the staff was so friendly the pool was really well taken care of and I only and short walk from the beach you really can’t beat the price I will be back!
Reviewed on May 13, 2026
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
The price is $376 total per night from May 16 to May 17
$376 total
per night
May 16 - May 17
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! (2,284 reviews)
Staff were very kind and helpful from check in to check out. À la carte restaurant meals were delicious! Grill by the pool was also awesome~ Greek salad and cheeseburgers were really good. Ideal location to enjoy lunch looking out at the water from the beach or poolside. Buffet was simple with a ...
Reviewed on May 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
Fully refundableReserve now, pay when you stay
The price is $264 total per night from Jun 15 to Jun 16
$264 total
per night
Jun 15 - Jun 16
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! (1,723 reviews)
Best resort I’ve stayed in yet ! Only thing I would say is that security should work on being nicer
Reviewed on May 14, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
The price is $354 total per night from May 26 to May 27
$354 total
per night
May 26 - May 27
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)
2 bedrooms for 5 adults with a beach view. Beautiful view of the sunset. The staff was friendly and helpful. Made our reservations to restaurants and tours. The rooms were clean and compact but had all that was needed for comfort-kitchen, dining area, balcony with chairs. Great Views. A roller bed ...
Reviewed on May 15, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
The price is $536 total per night from May 16 to May 17
$536 total
per night
May 16 - May 17
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! (1,000 reviews)
My family and I, along with some friends visited Aruba for a 2nd time and loved it. For our stay at Divi Phoenix, the resort is beautiful overall. However, I was disappointed with the constant beeping in my room my entire stay. Made it hard to sleep. No clue what it was but I reported it to the front ...
Reviewed on May 11, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
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! (1,994 reviews)
Great hotel and staff
Reviewed on May 12, 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
The price is $305 total per night from Jun 8 to Jun 9
$305 total
per night
Jun 8 - Jun 9
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 ...
9/10 Wonderful! (1,004 reviews)
Desde el momento que no se acercamos a la calzada de la calle, la experiencia fue única, el personal de recepción sumamente amable, cordial y respetuoso. Nos indicó las amenidades, horarios y todos los detalles importantes. Un hotel acogedor,súper tranquilo. Las camas súper cómodas. Nos sentimos ...
Reviewed on May 14, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
The price is $278 total per night from Jun 1 to Jun 2
$278 total
per night
Jun 1 - Jun 2
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! (2,567 reviews)
Very nice old hotel. Elegant. No complaints
Reviewed on May 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 $269 total per night from May 31 to Jun 1
$269 total
per night
May 31 - Jun 1
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! (1,676 reviews)
The staff was amazing. Especially Carlos at check-in and Nathaniel behind the bar! Room was clean and had everything we could have wanted. Loved it!
Reviewed on May 11, 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! (1,474 reviews)
Great activities. So much to do there is just
Reviewed on May 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.
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Carretera Bávaro Km. 1 Punta Cana La Altagracia
The price is $364 total per night from Jun 1 to Jun 2
$364 total
per night
Jun 1 - Jun 2
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! (5,591 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
Everything is wonderful except food.
Reviewed on May 15, 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! (6,622 reviews)
Had a great time
Reviewed on May 13, 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! (1,737 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! (4,850 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
As always, the Majestic was amazing. This was our 4th trip here and hopefully not last. The staff is so friendly and accommodating. Our room was always clean, and our butler would send someone right away if we had any issues. We will always recommend for people to stay here when visiting Punta ...
Reviewed on May 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.
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Caribbean
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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.