$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.
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | San Juan | October 18 to October 19 | $357 |
| EWR | Punta Cana | October 18 to October 22 | $396 |
| JFK | Montego Bay | October 16 to October 22 | $437 |
| EWR | Montego Bay | October 17 to October 20 | $462 |
| JFK | Santiago de los Caballeros | October 18 to November 1 | $467 |
| JFK | Santiago de los Caballeros | October 18 to November 1 | $467 |
| EWR | Santo Domingo | October 16 to November 24 | $472 |
| JFK | Nassau | October 18 to October 26 | $476 |
| JFK | Piarco | October 18 to October 26 | $493 |
| EWR | Nassau | October 17 to October 23 | $499 |
| JFK | Santo Domingo | October 18 to November 2 | $504 |
| JFK | Kingston | October 18 to November 18 | $525 |
| JFK | Kingston | October 18 to November 18 | $525 |
| EWR | Piarco | October 16 to October 20 | $563 |
| EWR | Kingston | October 17 to October 20 | $595 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
"We had a great stay! The staff was exceptionally friendly and welcomed us right away. Very convenient location and the free breakfast is a plus. The best part is you get free daily access to Atlantis which was amazing!! This is the best value on Paradise Island."
Reviewed on Oct 12, 2026
Coral by the Sea Hotel
"La estadía fue buena, se nos fue la luz en la habitación y rápido nos cambiaron de habitación a una mejor y espaciosa. La piscina buena pero el agua está demasiada fría."
Reviewed on Oct 12, 2026
Breezes Resort Bahamas All Inclusive
"Breezes is on beach, hotel was nice but does need updating,( work is being done at moment, they have retiled pools, hung hammocks on ground floor) Rooms have dark wood furniture so makes room seem dark, need to add kettles, Fridge and sofas in room to make it feel cosy, Staff are happy and friendly ..."
Reviewed on Oct 11, 2026
Meridian Inn
"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
Our Top Caribbean Apartment Hotels
Simpson Bay Resort, Marina & Spa
Amsterdam Manor Beach Resort
"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
"Great stay. Property was beautiful and clean"
Reviewed on Oct 11, 2026
Eagle Aruba Resort
Score Epic Caribbean Accommodation Deals
Hotel El Convento
"Our room was very comfortable and airy. The inside lock latch hook needed some repair and the safety box did not work, but otherwise a very nice room. The staff was very pleasant, friendly and helpful!"
Reviewed on Oct 12, 2026
British Colonial - Nassau
"The hotel is incredible clean and comfortable. BUT the menus at minimal to choose at any of the restaurants, I felt there not to many options ."
Reviewed on Oct 12, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
"Great 3 night stay and will return for a future trip."
Reviewed on Oct 12, 2026
The Reef at Atlantis
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Families like: Outdoor pools, waterslide, kids club, playground
"Las"
Reviewed on Oct 12, 2026
Majestic Colonial Punta Cana - All Inclusive
Dreams Rose Hall Resort & Spa - All Inclusive
Families like: Outdoor pools, free waterpark access, kids club, playground
"All was good"
Reviewed on Jan 15, 2026
Majestic Elegance Punta Cana - All Inclusive
Families like: Outdoor pools, waterslide, kids club, playground
Need a Car For After Your Flight?
Economy
Compact
Midsize
SUV
Caribbean
Snag some “suite” deals when you add cheap hotel rooms to Caribbean flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.
Budget Prices, Luxury Life
Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Caribbean.
Fun for All
While shopping Orbitz sales on Caribbean flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.
Non-Stop or Stop and Visit
Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Caribbean flights, you will always find the best air travel prices at Orbitz.
All in One
Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Caribbean. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.
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.