Cheap Flights to Caribbean from $89 (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*
JFKSan JuanMarch 24 to April 1$175
JFKSan JuanMarch 24 to April 1$175
LGASanto DomingoMay 5 to May 9$266
JFKMontego BayApril 5 to April 12$278
JFKMontego BayApril 5 to April 12$278
EWRPunta CanaApril 25 to May 2$280
EWRSanto DomingoApril 13 to April 22$280
EWRSantiago de los CaballerosApril 6 to April 26$290
JFKOranjestadApril 20 to April 24$333
JFKSantiago de los CaballerosMay 11 to May 12$341
EWRKingstonMarch 14 to March 18$351
JFKNassauMarch 23 to April 20$360
JFKWest EndMarch 15 to March 17$399
JFKWest EndMarch 15 to March 17$399
JFKKingstonMay 26 to May 28$423
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
EWRSan JuanMarch 1 to March 4$242
JFKSan JuanFebruary 28 to March 5$266
EWRNassauMarch 1 to March 16$374
EWRNassauMarch 1 to March 16$374
JFKPiarcoFebruary 28 to March 6$399
EWROranjestadFebruary 28 to March 3$417
EWROranjestadFebruary 28 to March 3$417
EWRSantiago de los CaballerosMarch 1 to March 12$421
JFKNassauFebruary 28 to March 3$429
JFKSantiago de los CaballerosFebruary 28 to March 6$442
JFKPunta CanaFebruary 28 to March 11$457
JFKPunta CanaFebruary 28 to March 11$457
EWRPunta CanaMarch 1 to March 6$497
JFKSanto DomingoMarch 1 to March 4$510
JFKSanto DomingoMarch 1 to March 4$510
*Prices include taxes and fees

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! (1,001 reviews)
Staff was excellent. Free bottle of wine each night in our room for booking through Hotels.com Room was impeccably clean and as advertised

Reviewed on Feb 25, 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! (2,294 reviews)
Beautiful hotel! Excellent location. Will definitely be back. I’ve visited Bahamas several times over the years and this might be my favorite so far!

Reviewed on Feb 26, 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! (1,540 reviews)
I was very disappointed when I got there. The customer service was awful. Our room was not ready and no one really cared much and we had several little kids. I didn’t think the staff was very understanding. Also was promised to be compensated for all the problems and nothing happened. I expected ...

Reviewed on Feb 26, 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.
9/10 Wonderful! (1,425 reviews)
The resort was gorgeous, clean and well-kept. The room was comfortable and clean and spacious. The ocean view from the 20th floor was amazing. The small kitchen amenities were excellent and served the purpose of most breakfasts for the family with a small fridge, microwave, cook top with frying pan ...

Reviewed on Feb 25, 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 $175. 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 April. 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 $175. 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 $175 and $510 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.