$99 Cheap flights to Caribbean
Top places to visit in Caribbean
Cheap flights to Caribbean from $99 One Way, $270 Round Trip
$270 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
SDQ
Santo Domingo
$270 Roundtrip, found 9 hours ago
$270
Roundtrip
found 9 hours ago
EWR
New York
SJU
San Juan
$278 Roundtrip, just found
$278
Roundtrip
just found
EWR
New York
AUA
Oranjestad
$298 Roundtrip, found 10 hours ago
$298
Roundtrip
found 10 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
SJU
San Juan
$312 Roundtrip, found 8 hours ago
$312
Roundtrip
found 8 hours ago
JFK
New York
AUA
Oranjestad
$315 Roundtrip, just found
$315
Roundtrip
just found
EWR
New York
AUA
Oranjestad
$315 Roundtrip, found 15 hours ago
$315
Roundtrip
found 15 hours ago
JFK
New York
SJU
San Juan
$332 Roundtrip, found 8 hours ago
$332
Roundtrip
found 8 hours ago
JFK
New York
SJU
San Juan
$337 Roundtrip, just found
$337
Roundtrip
just found
JFK
New York
STI
Santiago de los Caballeros
$344 Roundtrip, found 13 hours ago
$344
Roundtrip
found 13 hours ago
JFK
New York
MBJ
Montego Bay
$360 Roundtrip, just found
$360
Roundtrip
just found
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | San Juan | October 3 to October 17 | $288 |
| EWR | San Juan | October 3 to October 17 | $288 |
| JFK | San Juan | October 2 to October 3 | $402 |
| EWR | Nassau | October 2 to October 4 | $429 |
| EWR | Montego Bay | October 3 to October 16 | $451 |
| JFK | Punta Cana | October 3 to October 7 | $474 |
| JFK | Punta Cana | October 3 to October 7 | $474 |
| EWR | Kingston | October 3 to October 6 | $477 |
| EWR | Santiago de los Caballeros | October 4 to November 3 | $486 |
| EWR | Santiago de los Caballeros | October 4 to November 3 | $486 |
| JFK | Santo Domingo | October 2 to October 6 | $494 |
| JFK | Oranjestad | October 2 to October 3 | $498 |
| EWR | Piarco | October 3 to October 6 | $535 |
| JFK | Piarco | October 2 to October 10 | $540 |
| JFK | Kingston | October 3 to October 11 | $708 |
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 12 to Oct 13
$366 total
Oct 12 - Oct 13
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 26 to Oct 27
$113 total
Oct 26 - Oct 27
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! (2,457 reviews)
"Quality meals and great beach access"
Reviewed on Sep 24, 2026
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
$183 nightly
The price is $191 total per night from Oct 12 to Oct 13
$191 total
Oct 12 - Oct 13
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! (2,072 reviews)
"I enjoyed the stay"
Reviewed on Sep 26, 2026
Amsterdam Manor Beach Resort
J.E. Irausquin Boulevard 252 Noord
Fully refundableReserve now, pay when you stay
$304 nightly
The price is $341 total per night from Sep 29 to Sep 30
$341 total
Sep 29 - Sep 30
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 Sep 27 to Sep 28
$604 total
Sep 27 - Sep 28
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 ...
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
$322 nightly
The price is $372 total per night from Oct 27 to Oct 28
$372 total
Oct 27 - Oct 28
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
Fully refundableReserve now, pay when you stay
$339 nightly
The price is $370 total per night from Oct 25 to Oct 26
$370 total
Oct 25 - Oct 26
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 Sep 28 to Sep 29
$300 total
Sep 28 - Sep 29
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! (3,068 reviews)
"I can't say enough how blessed I was to stay here! I had a random herniated disk in my back while staying there. The pain was so intense I had to go to the hospital twice. The staff there went above and beyond assisting me and my family with everything we needed. Wheelchairs, pushing me back and ..."
Reviewed on Sep 25, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $178 total per night from Oct 4 to Oct 5
$178 total
Oct 4 - Oct 5
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 1 to Oct 2
$279 total
Oct 1 - Oct 2
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 ...
8/10 Very Good! (6,162 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"Oky........................"
Reviewed on Sep 26, 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! (1,464 reviews)
Families like: Outdoor pools, free waterpark access, kids club, playground
Travelers say...
"All was good"
Reviewed on Jan 15, 2026
Save an average of 15% on thousands of hotels when you're signed in
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.
Need a Car For After Your Flight?
Economy
Chevrolet Spark
Compact
Ford Focus
Midsize
Toyota Corolla
SUV
Jeep Compass
