$104 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $104 One Way, $211 Round Trip
$211 return flights and $104 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 30 to November 10 | $336 |
| JFK | San Juan | October 31 to November 13 | $347 |
| JFK | Montego Bay | November 1 to November 5 | $382 |
| JFK | Montego Bay | November 1 to November 5 | $382 |
| JFK | Oranjestad | October 31 to November 5 | $386 |
| JFK | Punta Cana | November 1 to November 3 | $401 |
| JFK | Punta Cana | November 1 to November 3 | $401 |
| EWR | Santo Domingo | October 30 to November 4 | $408 |
| JFK | Santo Domingo | October 30 to November 3 | $409 |
| JFK | Nassau | November 1 to November 5 | $422 |
| EWR | Kingston | November 1 to November 12 | $479 |
| EWR | Santiago de los Caballeros | November 1 to December 2 | $486 |
| JFK | Piarco | November 1 to November 11 | $541 |
| JFK | Santiago de los Caballeros | October 31 to November 11 | $541 |
| JFK | Kingston | October 31 to November 7 | $604 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
"Very helpful polite staff"
Reviewed on Oct 22, 2026
Coral by the Sea Hotel
Breezes Resort Bahamas All Inclusive
"1000/10 recommend!! I had an amazing time here and I’ll definitely be back. I felt extremely safe and catered to as a solo female traveler. The staff were always friendly and helpful. They all have a warmth and sweetness to them that made me feel welcomed. The room was perfectly cleaned. I requested ..."
Reviewed on Oct 22, 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
"My birthday was ruined by too much confusion."
Reviewed on Oct 23, 2026
Amsterdam Manor Beach Resort
"Excellent location, staff were very helpful especially Jenifer. Would stay there again."
Reviewed on Oct 22, 2026
Divi Aruba Phoenix Beach Resort
"We loved it all!"
Reviewed on Oct 22, 2026
Eagle Aruba Resort
"We've been to Eagle Aruba multiple times now and it is always up to great standards. The staff is interactive and pleasant. The amenities are wonderful and such a great location."
Reviewed on Oct 22, 2026
Score Epic Caribbean Accommodation Deals
Hotel El Convento
"Stunning property. Would love more towels and toilet paper, but very friendly and responsive staff"
Reviewed on Oct 19, 2026
British Colonial - Nassau
"Me encantó ! Un hotel súper acogedor bonito todo en buen estado súper limpio la playa privada súper linda , se ven los cruceros cuando llegan la cómida súper buena la atención del personal maravillosa definitivamente regresaremos por más días"
Reviewed on Oct 22, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
"Excelente experiencia"
Reviewed on Oct 23, 2026
The Reef at Atlantis
"This place was wonderful. Highly recommend!"
Reviewed on Oct 22, 2026
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
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
"The hotel was beautiful, luxurious feel. The staff were kind and very helpful. They made my birthday feel special. Me and my partner really enjoyed our stay."
Reviewed on Oct 23, 2026
Need a Car For After Your Flight?
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Caribbean
End your search for discount fares on flights to Caribbean. Orbitz has all the best prices on Caribbean flights. With Orbitz, you can expect:
Cheap Deals on Flights to Caribbean
We offer big discounts and last-minute savings on Caribbean flights. We make it easy for you to research, plan, and book your flight to Caribbean — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.
Travel Convenience on the Go
Get alerts, updates, or book your Caribbean flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Caribbean flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Caribbean flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.
Great Customer Care
We want to make your travel booking experience smooth and easy, from planning and researching Caribbean flights to the actual booking. If you want to cancel your flight to Caribbean, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.
Miles or Points Toward Frequent Flyer Programs
Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Caribbean with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.
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.