Cheap Flights to Caribbean from $62 (2026/2027)

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How Much Does it Cost To Fly To Caribbean?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

OriginDestinationTravel DatesFlights From*
EWRSan JuanFebruary 24 to March 4$144
EWRSan JuanFebruary 24 to March 4$144
JFKSan JuanApril 13 to April 22$148
LGAPunta CanaFebruary 24 to February 26$238
EWRSanto DomingoMarch 4 to March 11$260
LGASanto DomingoMarch 3 to March 10$260
EWRMontego BayMarch 1 to March 4$276
JFKSantiago de los CaballerosMarch 10 to March 11$291
LGAPiarcoMarch 10 to March 17$298
JFKSanto DomingoMarch 16 to March 17$302
EWRNassauFebruary 28 to March 3$323
JFKPiarcoMarch 3 to March 9$324
LGAKingstonMay 12 to May 19$361
JFKWest EndMarch 25 to March 31$399
JFKWest EndMarch 25 to March 31$399
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
FLLSanto DomingoFebruary 14 to February 20$210
EWRSan JuanFebruary 15 to February 25$375
LGAPunta CanaFebruary 15 to February 20$462
EWROranjestadFebruary 15 to February 17$508
EWROranjestadFebruary 15 to February 17$508
JFKSanto DomingoFebruary 15 to February 19$523
JFKSanto DomingoFebruary 15 to February 19$523
EWRSanto DomingoFebruary 14 to February 17$546
JFKNassauFebruary 14 to February 17$589
BOSMontego BayFebruary 13 to February 16$596
JFKOranjestadFebruary 15 to February 17$622
EWRMontego BayFebruary 15 to February 18$668
BOSPiarcoFebruary 15 to February 22$694
JFKPiarcoFebruary 15 to February 15$714
JFKMontego BayFebruary 14 to February 16$745
*Prices include taxes and fees

Best Caribbean Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Silver Creek Resort
Ola Boutique Hotel
Sunset at the Palms Resort - Adults Only - All Inclusive
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Travelers ❤️ These Caribbean 🏨

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St San Juan
Book a stay at this luxury hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Pan American Pier are located nearby.
9/10 Wonderful! (1,003 reviews)
Beautiful place in the middle of Old San Juan . Excellent location. The building and rooms are beautiful . Well maintained keeping the beautiful architecture and original old structures .

Reviewed on Feb 5, 2026

Opens in a new windowHotel El Convento
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
Number One Bay St Nassau
Book a stay at this beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 8 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cable Beach and Pirates of Nassau Museum are located nearby.
8.4/10 Very Good! (2,248 reviews)
Great Staff

Reviewed on Feb 7, 2026

Opens in a new windowBritish Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

4 out of 5
100 Brumbaugh Street San Juan Puerto Rico
Book a stay at this business-friendly hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Pan American Pier are located nearby.
9/10 Wonderful! (1,508 reviews)
Clean room, great mattress, help full staff, close to cruise ship. All in all a GREAT experience.

Reviewed on Feb 3, 2026

Opens in a new windowHotel Rumbao, a Tribute Portfolio Hotel
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The Reef at Atlantis

The Reef at Atlantis

4.5 out of 5
Paradise Beach Drive Paradise Island New Providence
Book a stay at this luxury resort in Paradise Island. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Cable Beach and Aquaventure are located nearby.
8.8/10 Excellent! (1,426 reviews)
Great as always!

Reviewed on Feb 7, 2026

Opens in a new windowThe Reef at Atlantis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Caribbean?
Your next vacation doesn't have to make a huge dent in your budget. During the last seven days, the cheapest roundtrip flight to Caribbean cost $123. Find a cheap ticket and spend the money you save on cool experiences. This price was available on Travelocity for flights to Caribbean departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Caribbean?
Pack your bags and jet off with any of the 15 airlines that fly to Caribbean. Make a booking with popular air carrier, Sunrise Airways. It has approximately 43 flights per month to Santo Domingo, Caribbean's premier city, so finding a fare that suits should be a snap.
What is the cheapest month to fly to Caribbean?
Spend more money on great adventures rather than airfares by zipping off to Caribbean in February. This is the best-priced month to jet out to this place according to Travelocity's direct return flight demand from January to December last year. Browse through our range of flights and enjoy a change of scenery without emptying your bank account.
How can I check my flight status to Caribbean?
Check for updates on your flight to Caribbean, make changes and much more from our "Trips" customer portal. Found at the top right of our homepage, it's your gateway to viewing your bookings. Just log in or open an account in seconds. Savvy wanderers can also take advantage of the Travelocity app. You'll get real-time trip updates, along with the ability to book hotels, rental cars and activities while you're on the go. If you have friends or family flying with you, it's also a quick way to share travel info with each other.
How do I find the best deals on flights to Caribbean?
It's always good to book ahead of schedule, and if possible, avoid traveling during the busy tourist season. Another great way to save is by hitting the "Flexible dates" box at the top of the page after searching for your flights. This will show you ticket prices for nearby days. In the last seven days, the lowest price for a return flight to Caribbean was $123. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Caribbean with Travelocity?
Pack your case and get set to take off with Travelocity. It's our job to find you fantastic deals on cheap flights to Caribbean. Whether you want flexible airfares with plenty of wiggle room or cheap family flights on budget carriers, we've got what you need.
How much is a flight to Caribbean on average?
Plane tickets for roundtrip flights to Caribbean cost between $123 and $745 in the last seven days. The moment you find an incredible deal, lock it in and get ready to set off on the getaway of your dreams with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What can I expect on a flight to Caribbean?
The duration of your flight and whether you're flying with a full-service or low-priced airline play a major role. If you're searching for long-haul flights to Caribbean, drinks, food and entertainment will often be included. Want cheap flights for family vacations? You'll save with budget carriers. These airlines usually don't have as many inclusions, so be prepared to pay for food and drinks.