
$39 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $39 One Way, $78 Round Trip
$78 return flights and $39 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 | July 19 to August 1 | $367 |
| EWR | San Juan | July 19 to July 29 | $377 |
| LGA | Oranjestad | July 18 to July 24 | $427 |
| JFK | Oranjestad | July 18 to July 22 | $445 |
| EWR | Piarco | July 17 to July 29 | $449 |
| EWR | Nassau | July 19 to July 22 | $492 |
| LGA | Montego Bay | July 18 to July 20 | $507 |
| JFK | Santiago de los Caballeros | July 18 to July 23 | $548 |
| JFK | Santiago de los Caballeros | July 18 to July 23 | $548 |
| EWR | Montego Bay | July 19 to August 14 | $562 |
| JFK | Piarco | July 17 to July 31 | $565 |
| JFK | Montego Bay | July 18 to July 21 | $577 |
| JFK | Punta Cana | July 17 to July 19 | $659 |
| JFK | Kingston | July 19 to July 29 | $671 |
| EWR | Santo Domingo | July 17 to July 26 | $732 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals

Comfort Suites Paradise Island
"The property was very conveniently located.It was in pretty good shape.The staff was nice and helpful.The pool was pretty good and the restaurant was decent"
Reviewed on Jul 14, 2026

Coral by the Sea Hotel
"I’ll start off with the positives. The STAFF are amazing and do their best. Very kind and helpful & you can tell. Location is great, everything walking distance. Air conditioner was great. Again, Love love love the staff & gift shop next door has detergent for laundry and pads for menstrual for cheap, ..."
Reviewed on Jul 14, 2026

Breezes Resort Bahamas All Inclusive
"Resort staff was excellent!"
Reviewed on Jul 14, 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
"Excellent location, clean and very comfortable.!"
Reviewed on Jul 14, 2026

Amsterdam Manor Beach Resort
"L"
Reviewed on Jul 13, 2026

Divi Aruba Phoenix Beach Resort
"It was amazing"
Reviewed on Jul 14, 2026

Eagle Aruba Resort
"We stayed 8 nights (7-2026) at the Eagle Aruba. The staff was friendly & the room was clean. We had a 1 bedroom suite with a kitchen on the 4th floor overlooking the waterfall pool. The room had a pull-out sofa sleeper as well as 2 double beds. The beds were very comfortable with plenty of pillows ..."
Reviewed on Jul 14, 2026
Score Epic Caribbean Accommodation Deals

Hotel El Convento
"Love this property! Best hotel in the Old San Juan. Courteous staff, beautiful grounds, extremely clean and we loved the coffee / water bar on the 3rd floor with the terrace overlooking the city. They even upgraded us to a suite for no additional charge. We will be back!"
Reviewed on Jul 12, 2026

British Colonial - Nassau
"Je n’ai pratiquement pas dormi durant tout mon séjour. Le réfrigérateur dans la chambre faisait beaucoup trop de bruit. De plus, votre site indiquait que la réservation incluait un « accès VIP », mais je n’ai bénéficié d’aucun avantage ou service correspondant à cette mention. J’ai trouvé le prix ..."
Reviewed on Jul 14, 2026

Hotel Rumbao, a Tribute Portfolio Hotel
"Great place to stay!"
Reviewed on Jul 14, 2026

The Reef at Atlantis
"Staff were great!"
Reviewed on Jul 13, 2026
Family Friendly Hotels in Caribbean

Barceló Bávaro Palace - All Inclusive
Families like: Outdoor pools, waterslide, kids club, playground
"First off, this resort is massive! They have trolleys going around about every 5 mins which helped out with all the walking. We arrived 2 hrs early but was allowed to check in early. Right after checking in, we went to concierge to make reservations for the restaurants but they told us that every ..."
Reviewed on Jul 14, 2026

Majestic Colonial Punta Cana - All Inclusive
"Terrible food and place needed to be upgraded"
Reviewed on Jun 9, 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
"."
Reviewed on Jul 13, 2026
Need a Car For After Your Flight?
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Caribbean
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Low Price Guarantee
Booking your Caribbean flights with Orbitz guarantees low prices every day, all day—no matter when and where you book. You will always find the best deals available, coupled with extra great savings and discounts for all around great value.
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.











