Cheap Flights to Caribbean from $44 (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 9 to February 11$130
JFKSan JuanApril 14 to April 23$148
EWRPunta CanaFebruary 9 to February 13$235
LGASantiago de los CaballerosFebruary 9 to February 10$238
EWRSanto DomingoFebruary 9 to February 12$244
EWRSanto DomingoFebruary 9 to February 12$244
JFKPunta CanaMay 2 to May 2$256
JFKSantiago de los CaballerosMarch 17 to March 18$270
JFKNassauFebruary 21 to February 28$289
JFKSanto DomingoMarch 9 to March 10$292
JFKOranjestadFebruary 22 to February 28$298
JFKPiarcoApril 15 to April 30$303
JFKMontego BayApril 18 to April 25$342
JFKWest EndFebruary 22 to February 28$399
JFKKingstonMarch 18 to April 15$413
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKSan JuanJanuary 31 to February 6$127
EWRSan JuanJanuary 31 to February 7$143
EWRSanto DomingoJanuary 31 to February 10$280
EWRSanto DomingoJanuary 31 to February 10$280
EWRPunta CanaJanuary 31 to February 5$299
EWRPunta CanaJanuary 31 to February 5$299
JFKSantiago de los CaballerosFebruary 1 to February 5$332
JFKSantiago de los CaballerosFebruary 1 to February 5$332
JFKPunta CanaFebruary 1 to February 5$339
EWRNassauJanuary 31 to February 5$417
JFKNassauJanuary 31 to February 5$417
EWRKingstonFebruary 1 to February 12$418
JFKWest EndFebruary 1 to February 3$419
JFKWest EndFebruary 1 to February 3$419
JFKKingstonJanuary 31 to March 13$476
*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! (1,000 reviews)
Hotel is gorgeous, excellent location with walking distant to old San Juan main attractions. Staff was excellent. Highly recommended!

Reviewed on Jan 20, 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.
8.6/10 Excellent! (2,188 reviews)
Room was clean , and stuff very nice and welcoming

Reviewed on Jan 21, 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! (1,476 reviews)
The restaurant area was not very clean. And the staff is not very nice behind the desk, but it was a good location.

Reviewed on Jan 23, 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! (1,418 reviews)
Clean room, clean resort and very friendly staff with the exception of the shuttle drivers.

Reviewed on Jan 24, 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 $97. 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 18 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 January. 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 $97. 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 $97 and $476 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.