$55 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $55 One Way, $191 Round Trip
$191 return flights and $55 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 | Oranjestad | November 21 to November 25 | $330 |
| JFK | Montego Bay | November 22 to November 25 | $416 |
| JFK | Montego Bay | November 22 to November 25 | $416 |
| JFK | Punta Cana | November 21 to November 22 | $416 |
| JFK | Punta Cana | November 21 to November 22 | $416 |
| JFK | Santiago de los Caballeros | November 22 to December 27 | $424 |
| JFK | Santiago de los Caballeros | November 22 to December 27 | $424 |
| EWR | Nassau | November 20 to November 23 | $425 |
| JFK | Santo Domingo | November 22 to December 12 | $435 |
| EWR | Kingston | November 22 to November 26 | $439 |
| EWR | Kingston | November 22 to November 26 | $439 |
| JFK | Nassau | November 21 to November 25 | $452 |
| JFK | San Juan | November 21 to December 26 | $457 |
| JFK | Piarco | November 20 to November 24 | $470 |
| JFK | Oranjestad | November 22 to November 30 | $499 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
Coral by the Sea Hotel
Breezes Resort Bahamas All Inclusive
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
"I have written my story to the General management.I had 3 days of hell.Ac not working no TV bathroom toilet not working had to use the public restroom and was moved at 3;00 am to another room so that we can sleep in a room with a working bathroom only to be moved back to the same room toilet not ..."
Reviewed on Nov 13, 2026
Amsterdam Manor Beach Resort
"We love it"
Reviewed on Nov 13, 2026
Divi Aruba Phoenix Beach Resort
Eagle Aruba Resort
"This is the third time we’ve stayed at Eagle Beach Resort and it’s always a great stay"
Reviewed on Nov 13, 2026
Score Epic Caribbean Accommodation Deals
Hotel El Convento
"This hotel is 4.5. The location is excellent; the building is charming with a fantastic interior courtyard filled with tropical plants and a very good bar. My one reservation is about the flexibility of breakfast when included in your room rate. You are given a voucher for each morning meal and it ..."
Reviewed on Nov 12, 2026
British Colonial - Nassau
"We had no hot water 5 days"
Reviewed on Nov 12, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
The Reef at Atlantis
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Majestic Colonial Punta Cana - All Inclusive
"We were in the hotel the first day from re-opening (november 7th). Staff 10/10 Bar 10/10 In our room the hot tub outside wasn’t working. There were just 2 restaurants opened: Taino and La Hispaniola. They offered us the Club so We could go to Mirage and Elegance In general, I rate my experience 8/10. ..."
Reviewed on Nov 12, 2026
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
"Everything was very good , clean and organized. The food was great and the staff there was very friendly and welcoming. Thanks Majestic Elegance Hotel , and a big thank you to all the staff there for the hard work that they do . Highly recommend it !!!!"
Reviewed on Nov 13, 2026
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Caribbean
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Ports and Play
Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Caribbean and Caribbean flights. Get more bang for your travel buck at Orbitz.
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.