$99 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $99 One Way, $243 Round Trip
$243 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
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
JFK
New York
SJU
San Juan
$296 Roundtrip, just found
$296
Roundtrip
just found
BOS
Boston
SJU
San Juan
$300 Roundtrip, just found
$300
Roundtrip
just found
JFK
New York
NAS
Nassau
$306 Roundtrip, found 2 hours ago
$306
Roundtrip
found 2 hours ago
EWR
New York
AUA
Oranjestad
$308 Roundtrip, found 4 days ago
$308
Roundtrip
found 4 days ago
JFK
New York
SDQ
Santo Domingo
$310 Roundtrip, found 1 day ago
$310
Roundtrip
found 1 day ago
JFK
New York
STI
Santiago de los Caballeros
$318 Roundtrip, found 3 hours ago
$318
Roundtrip
found 3 hours ago
JFK
New York
AUA
Oranjestad
$324 Roundtrip, found 1 day ago
$324
Roundtrip
found 1 day ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | October 17 to October 20 | $407 |
| JFK | San Juan | October 17 to October 20 | $407 |
| EWR | San Juan | October 18 to October 21 | $407 |
| EWR | Oranjestad | October 18 to October 24 | $413 |
| JFK | Santo Domingo | October 18 to October 25 | $431 |
| JFK | Santo Domingo | October 18 to October 25 | $431 |
| JFK | Montego Bay | October 17 to October 30 | $434 |
| JFK | Montego Bay | October 17 to October 30 | $434 |
| EWR | Santo Domingo | October 16 to October 19 | $491 |
| EWR | Santiago de los Caballeros | October 18 to October 25 | $492 |
| JFK | Piarco | October 16 to October 22 | $493 |
| JFK | Piarco | October 16 to October 22 | $493 |
| JFK | Santiago de los Caballeros | October 16 to November 15 | $499 |
| JFK | Kingston | October 18 to November 18 | $540 |
| JFK | Punta Cana | October 18 to October 22 | $582 |
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 25 to Oct 26
$366 total
Oct 25 - Oct 26
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! (2,461 reviews)
"Our stay was great I love it. I loved their wings from the restaurant"
Reviewed on Oct 10, 2026
Coral by the Sea Hotel
Calle Rosa 2 Carolina
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $101 total per night from Oct 11 to Oct 12
$101 total
Oct 11 - Oct 12
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
$161 nightly
The price is $169 total per night from Oct 14 to Oct 15
$169 total
Oct 14 - Oct 15
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! (2,100 reviews)
"We loved the resort. There’s something for everyone there. The restaurants were great, Laura at the pool bar was awesome . The workers were always at work cleaning the property . It was so clean . Everyone there made you feel like family even the guests we met at the pool, at the restaurants, by ..."
Reviewed on Oct 10, 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. ...
9.6/10 Exceptional! (1,001 reviews)
"We had a lovely stay at Amsterdam Manor! The hotel was clean, quiet, and conveniently located close to the beach. The staff were friendly and welcoming. A wonderful place for a relaxing vacation!"
Reviewed on Oct 9, 2026
Divi Aruba Phoenix Beach Resort
J E Irausquin Boulevard 75 Noord
$541 nightly
The price is $612 total per night from Oct 11 to Oct 12
$612 total
Oct 11 - Oct 12
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
$369 nightly
The price is $428 total per night from Nov 10 to Nov 11
$428 total
Nov 10 - Nov 11
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! (1,815 reviews)
"The hotel itself was okay. Pools were nice. The rooms were not clean at all. We had a roach -a big one . We went down to front desk - it was 11 pm. We were tired from our night out and offered little help. They said cleaning crew was unavailable. No apology at all. We had to move are room from 1st ..."
Reviewed on Oct 8, 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
$392 nightly
The price is $427 total per night from Oct 13 to Oct 14
$427 total
Oct 13 - Oct 14
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 ...
9.4/10 Exceptional! (1,005 reviews)
"The hotel staff were always around to help answer any questions or concerns. The staff worked very hard to make our vacation very relaxing and enjoyable. The free wine and cheese hour from 5pm until 6Pm was an excellent way to relax and meet people staying at the hotel. The free coffee and tea service ..."
Reviewed on Oct 10, 2026
British Colonial - Nassau
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
$270 nightly
The price is $296 total per night from Oct 12 to Oct 13
$296 total
Oct 12 - Oct 13
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! (3,104 reviews)
"Beautiful hotel with amazing service. The pool & beach areas are immaculate & constantly being maintained. Stunning rooms & overall historical building."
Reviewed on Oct 10, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $167 total per night from Oct 18 to Oct 19
$167 total
Oct 18 - Oct 19
Total with taxes and fees
Book a stay at this business-friendly hotel in San Juan. Enjoy free WiFi, a casino, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,963 reviews)
"This hotel is located conveniently in Old San Juan right next to a cruise ship dock. There is a Walgreen in the same building, so it's very easy to pick up daily essentials. The rooms have been renovated recently,"
Reviewed on Oct 10, 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! (1,716 reviews)
"Welcoming staff, clean place, breathtaking landscape and the beach is clean."
Reviewed on Oct 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.
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 21 to Oct 22
$279 total
Oct 21 - Oct 22
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 ...
Majestic Colonial Punta Cana - All Inclusive
Carretera El Macao Punta Cana La Altagracia
$303 nightly
The price is $303 total per night from Nov 8 to Nov 9
$303 total
Nov 8 - Nov 9
Total with taxes and fees
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Macao Beach and Arena Gorda ...
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! (1,450 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 ...
9/10 Wonderful! (5,246 reviews)
Families like: Outdoor pools, waterslide, kids club, playground
Travelers say...
"Had a wonderful time. Staff were super friendly and our butler Jose was amazing!!! Rooms and main pool does need a little maintenance."
Reviewed on Oct 10, 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
Why search for low cost fares on your flights to Caribbean when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:
Bargain Flights to Caribbean
Orbitz offers massive discounts and substantial last-minute savings on your Caribbean flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.
Cutting-Edge Mobile Tools to Keep You In The Know
Orbitz sends you free alerts and updates on your Caribbean flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.
Frequent Flyer Program Enrolment
Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Caribbean. When making your booking, reference your frequent flyer number to receive discounts in the future.
Outstanding Customer Service
Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Caribbean but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.
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.