$101 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $101 One Way, $236 Round Trip
$236 return flights and $101 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* |
|---|---|---|---|
| JFK | San Juan | October 24 to October 31 | $344 |
| JFK | Santo Domingo | October 25 to November 14 | $382 |
| JFK | Santo Domingo | October 25 to November 14 | $382 |
| EWR | Montego Bay | October 24 to October 27 | $390 |
| EWR | Montego Bay | October 24 to October 27 | $390 |
| LGA | Nassau | October 24 to October 28 | $394 |
| EWR | Oranjestad | October 25 to October 31 | $408 |
| EWR | Punta Cana | October 24 to October 29 | $420 |
| EWR | San Juan | October 24 to October 30 | $427 |
| EWR | Kingston | October 24 to October 27 | $493 |
| EWR | Kingston | October 24 to October 27 | $493 |
| JFK | Oranjestad | October 25 to October 27 | $497 |
| JFK | Montego Bay | October 24 to October 31 | $498 |
| JFK | Punta Cana | October 24 to October 28 | $519 |
| EWR | Piarco | October 23 to October 28 | $567 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
"Loved the pool area…the rooms are a little old looking but very clean. The cleaning staff and the life guards were amazing. The restaurant staff (one in particular) was very rude. The vouchers given on check in has too many restrictions."
Reviewed on Oct 17, 2026
Coral by the Sea Hotel
"Excelente"
Reviewed on Oct 18, 2026
Breezes Resort Bahamas All Inclusive
"*rooms were cleaned and cleaned well daily *staff was helpful, not rude, but not overly kind either. *food was okay. Plenty of choices with a decent amount of vegetarian options. * drinks are biggest complaint. No decaf coffee. Witnessed the watering down of their juice. Alcohol seemed watered down ..."
Reviewed on Oct 15, 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
"My family stayed at the penthouse and we are glad we chose here. The entire idea was a relaxed, no pressure vacation. We had planned no specific items, except lounging in the sea. Amazingly helpful staff who helped us book couple of activities when we felt the need to so something more. Took care ..."
Reviewed on Oct 17, 2026
Divi Aruba Phoenix Beach Resort
Eagle Aruba Resort
"This was the perfect resort for us. We loved everything about it! Clean, staff was so wonderful, and a perfect location to Eagle Beach."
Reviewed on Oct 16, 2026
Score Epic Caribbean Accommodation Deals
Hotel El Convento
British Colonial - Nassau
"Las habitaciones ninguna tienen balcón ,tienen cucarachas .cobran depósito 400 dólares.no tienen nada incluido demasiado caro todo.nunca ponen las toallas como debe ser según las personas ,para mí no se lo recomiendo a nadie no tiene nada divertido es solo para tercera edad.no hay animación en sí ..."
Reviewed on Oct 18, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
"Great ambience, customer service, pool and restaurant. Allowed us into room early- huge plus!"
Reviewed on Oct 17, 2026
The Reef at Atlantis
"We enjoyed our stay. The property is expansive, beautiful, and well maintained. The dining options were very limited (many of the restaurants were closed). Our room was great. It was surprising how great the kitchen in our room was equipped."
Reviewed on Oct 17, 2026
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Families like: Outdoor pools, waterslide, kids club, playground
"Overall great property, lack of music"
Reviewed on Oct 18, 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
"Our 10th time staying there! We love it so much. The staff is phenomenal! We already have our next trip booked to go back!"
Reviewed on Oct 17, 2026
Need a Car For After Your Flight?
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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.