$99 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $99 One Way, $253 Round Trip
$253 return flights and $99 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.
EWR
New York
SJU
San Juan
$253 Roundtrip, found 5 hours ago
$253
Roundtrip
found 5 hours ago
JFK
New York
AUA
Oranjestad
$303 Roundtrip, found 2 days ago
$303
Roundtrip
found 2 days ago
EWR
New York
PUJ
Punta Cana
$304 Roundtrip, found 1 hour ago
$304
Roundtrip
found 1 hour ago
EWR
New York
SDQ
Santo Domingo
$304 Roundtrip, just found
$304
Roundtrip
just found
JFK
New York
NAS
Nassau
$306 Roundtrip, found 8 hours ago
$306
Roundtrip
found 8 hours ago
EWR
New York
AUA
Oranjestad
$308 Roundtrip, found 12 hours ago
$308
Roundtrip
found 12 hours ago
EWR
New York
SJU
San Juan
$312 Roundtrip, found 1 day ago
$312
Roundtrip
found 1 day ago
EWR
New York
SJU
San Juan
$317 Roundtrip, found 1 hour ago
$317
Roundtrip
found 1 hour ago
JFK
New York
SJU
San Juan
$317 Roundtrip, found 1 hour ago
$317
Roundtrip
found 1 hour ago
JFK
New York
SDQ
Santo Domingo
$320 Roundtrip, just found
$320
Roundtrip
just found
JFK
New York
STI
Santiago de los Caballeros
$328 Roundtrip, found 2 days ago
$328
Roundtrip
found 2 days ago
JFK
New York
MBJ
Montego Bay
$358 Roundtrip, found 2 hours ago
$358
Roundtrip
found 2 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | San Juan | October 11 to October 19 | $353 |
| EWR | Montego Bay | October 10 to October 31 | $400 |
| JFK | San Juan | October 10 to October 14 | $407 |
| JFK | Oranjestad | October 11 to October 14 | $441 |
| LGA | Santiago de los Caballeros | October 10 to October 23 | $449 |
| JFK | Santo Domingo | October 11 to October 17 | $466 |
| JFK | Santo Domingo | October 11 to October 17 | $466 |
| JFK | Montego Bay | October 11 to October 25 | $476 |
| JFK | Santiago de los Caballeros | October 10 to October 15 | $500 |
| JFK | Nassau | October 11 to October 15 | $523 |
| JFK | Nassau | October 11 to October 15 | $523 |
| JFK | Piarco | October 9 to October 21 | $541 |
| JFK | Piarco | October 9 to October 21 | $541 |
| JFK | Kingston | October 9 to October 11 | $561 |
| JFK | Punta Cana | October 11 to October 17 | $617 |
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 18 to Oct 19
$366 total
Oct 18 - Oct 19
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 ...
8.4/10 Very Good! (2,463 reviews)
"We had a great stay!! comfort Suites is that a location accessible to all the Paradise Island and over to downtown Nassau. The staff was exceptionally pleasant and welcomed us right away. The daily breakfast was delicious, was about the same every morning, but you knew what you were getting and it ..."
Reviewed on Oct 4, 2026
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 Nov 3 to Nov 4
$113 total
Nov 3 - Nov 4
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 ...
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
$153 nightly
The price is $161 total per night from Oct 5 to Oct 6
$161 total
Oct 5 - Oct 6
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 ...
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 5 to Oct 6
$604 total
Oct 5 - Oct 6
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! (1,001 reviews)
"We stayed here with our kids and had a wonderful experience. The easy walk from the pool to the beach was especially convenient while traveling with children. Having a kitchen in the room made our stay more comfortable, and we appreciated that the hotel never felt overcrowded. Overall, it was a relaxing, ..."
Reviewed on Oct 1, 2026
Save an average of 15% on thousands of hotels when you're signed in
Eagle Aruba Resort
J. E. Irausquin Boulevard 248 Oranjestad
Fully refundableReserve now, pay when you stay
$318 nightly
The price is $370 total per night from Nov 4 to Nov 5
$370 total
Nov 4 - Nov 5
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! (1,819 reviews)
"muy cerca del supermercado y de la playa. lindas habitaciones"
Reviewed on Oct 3, 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
$419 nightly
The price is $457 total per night from Oct 5 to Oct 6
$457 total
Oct 5 - Oct 6
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! (1,009 reviews)
"Absolutely beautiful hotel will definitely be back"
Reviewed on Oct 3, 2026
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 5 to Oct 6
$300 total
Oct 5 - Oct 6
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 ...
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! (1,954 reviews)
"Great location! Walkable distance to the forts. The staff were very friendly."
Reviewed on Oct 3, 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 11 to Oct 12
$279 total
Oct 11 - Oct 12
Total with taxes and fees
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bavaro Beach and Downtown ...
8/10 Very Good! (6,195 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"."
Reviewed on Oct 3, 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! (1,455 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
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. Popular attractions Macao Beach and Arena Gorda ...
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
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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
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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.