$106 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $106 One Way, $234 Round Trip
$234 return flights and $106 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
$234 Roundtrip, found 2 days ago
$234
Roundtrip
found 2 days ago
JFK
New York
SJU
San Juan
$236 Roundtrip, found 2 days ago
$236
Roundtrip
found 2 days ago
JFK
New York
SJU
San Juan
$237 Roundtrip, found 3 hours ago
$237
Roundtrip
found 3 hours ago
EWR
New York
SJU
San Juan
$246 Roundtrip, found 3 hours ago
$246
Roundtrip
found 3 hours ago
EWR
New York
SJU
San Juan
$265 Roundtrip, found 1 hour ago
$265
Roundtrip
found 1 hour ago
EWR
New York
SJU
San Juan
$293 Roundtrip, found 1 day ago
$293
Roundtrip
found 1 day ago
EWR
New York
SJU
San Juan
$308 Roundtrip, found 5 hours ago
$308
Roundtrip
found 5 hours ago
EWR
New York
PUJ
Punta Cana
$315 Roundtrip, just found
$315
Roundtrip
just found
EWR
New York
SDQ
Santo Domingo
$315 Roundtrip, just found
$315
Roundtrip
just found
JFK
New York
NAS
Nassau
$318 Roundtrip, found 1 day ago
$318
Roundtrip
found 1 day ago
JFK
New York
SDQ
Santo Domingo
$322 Roundtrip, found 4 hours ago
$322
Roundtrip
found 4 hours ago
JFK
New York
MBJ
Montego Bay
$325 Roundtrip, just found
$325
Roundtrip
just found
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | August 15 to August 19 | $432 |
| EWR | Piarco | August 14 to August 19 | $453 |
| EWR | Piarco | August 14 to August 19 | $453 |
| EWR | San Juan | August 14 to August 16 | $462 |
| JFK | Santiago de los Caballeros | August 16 to September 1 | $550 |
| JFK | Santiago de los Caballeros | August 16 to September 1 | $550 |
| JFK | Piarco | August 15 to August 22 | $560 |
| JFK | Kingston | August 16 to August 30 | $602 |
| LGA | Punta Cana | August 16 to August 19 | $606 |
| EWR | Kingston | August 15 to August 20 | $636 |
| EWR | Montego Bay | August 15 to August 22 | $642 |
| JFK | Nassau | August 15 to August 18 | $717 |
| LGA | Oranjestad | August 16 to August 25 | $806 |
| EWR | Punta Cana | August 14 to August 17 | $835 |
| JFK | Oranjestad | August 15 to August 20 | $845 |
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 10 to Aug 11
$383 total
per night
Aug 10 - Aug 11
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
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 (2,430 reviews)
"This hotel is only good for the location and perhaps one night. For what I paid for the room it should be a whole lot nicer. The property is very dated and not upgraded. The staff was pleasant nobody was overly nice."
Reviewed on Aug 9, 2026
Breezes Resort Bahamas All Inclusive
1 Breezes Lane, Cable Beach Nassau New Providence
The price is $347 total per night from Aug 19 to Aug 20
$347 total
per night
Aug 19 - Aug 20
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! (2,392 reviews)
"The ocean view and beach were amazing. Everything else, literally everything else was awful. The food was very repetitive, staff was unenthusiastic to serve or help with anything, wifi was horrible, one restaurant open per night is a joke, beach grill was broken most of the trip, and the hotel is ..."
Reviewed on Aug 9, 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 $178 total per night from Sep 8 to Sep 9
$178 total
per night
Sep 8 - Sep 9
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! (1,941 reviews)
"Very kind staff , helpful with all my needs"
Reviewed on Aug 9, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
The price is $364 total per night from Aug 26 to Aug 27
$364 total
per night
Aug 26 - Aug 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! (1,005 reviews)
"Great as usual"
Reviewed on Aug 8, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
The price is $612 total per night from Aug 11 to Aug 12
$612 total
per night
Aug 11 - Aug 12
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! (1,014 reviews)
"Property was well maintained"
Reviewed on Aug 8, 2026
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Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
The price is $341 total per night from Sep 9 to Sep 10
$341 total
per night
Sep 9 - Sep 10
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! (1,884 reviews)
"Front desk was understaffed but all staff members were super kind."
Reviewed on Aug 9, 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 $222 total per night from Sep 1 to Sep 2
$222 total
per night
Sep 1 - Sep 2
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! (1,021 reviews)
"Perfect location in the middle of old town San Juan. Converted convent with unique atmosphere. Great rooms. Very helpful stuff. Free coffee until 12pm snd wine and free wine snd cheese reception every day 5-6pm were great. Good opportunity to meet some other guests. Pool and jacuzzi quite small but ..."
Reviewed on Aug 9, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
The price is $260 total per night from Sep 7 to Sep 8
$260 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 $223 total per night from Aug 30 to Aug 31
$223 total
per night
Aug 30 - Aug 31
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! (1,846 reviews)
"Clean room Nice staff Great food Great customer service Awesome location"
Reviewed on Aug 9, 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 17 to Aug 18
$287 total
per night
Aug 17 - Aug 18
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! (1,578 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! (4,958 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"Room clean hood enough for 3 stars. Staff does not understand english. Swim up bar was good. I would give 4 stars The pools need to maintenance The food litle salty Tennis courts and pickleball courts. Need to play early morning or afternoon after 5pm. Because the sun. Italy, Japanese and steak house ..."
Reviewed on Aug 9, 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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Discounted tickets available for flights to Caribbean
Orbitz offers tickets at a discounted, budget friendly rate that will satisfy all of your travel requirements. Book your Caribbean flights with us and structure a package that includes car hire, family activities and cheap accommodation. Orbitz will ensure that all your requirements are met, letting you relax and enjoy your holiday as it was intended.
Orbitz offers discounted Caribbean flights
Discounted flights to Caribbean ensure that all who want to travel can Take advantage of Orbitz’ guaranteed low prices and affordable packages. You will enjoy a hassle free trip, an up to date travel planner and friendly service.
Traveler profile updates
When flying with Orbitz, take advantage of frequent updates on your flights to Caribbean. Details and updates are sent to up to six contact numbers to ensure that you are kept abreast of the latest information on Caribbean flights. Frequent flyer and loyalty membership numbers may be updated within your Orbitz account profile.
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.