Cheap Flights to Caribbean from $50 (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*
LGASan JuanApril 22 to April 25$164
EWRSan JuanApril 25 to May 2$188
LGAPunta CanaMay 1 to May 5$263
JFKSan JuanApril 21 to April 22$295
EWRSanto DomingoApril 19 to April 22$297
LGAMontego BayApril 19 to April 25$302
JFKMontego BayMay 12 to May 15$309
JFKNassauApril 20 to April 24$343
JFKSanto DomingoApril 24 to April 25$348
JFKPiarcoJune 9 to June 23$350
JFKOranjestadMay 30 to June 6$354
EWRNassauApril 19 to April 23$360
LGASantiago de los CaballerosApril 20 to April 24$378
JFKSantiago de los CaballerosMay 10 to May 10$378
JFKWest EndMay 1 to May 5$473
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
EWRSan JuanApril 5 to April 8$265
EWRSan JuanApril 5 to April 8$265
EWRNassauApril 4 to April 7$392
EWRNassauApril 4 to April 7$392
JFKNassauApril 4 to April 7$422
LGAPiarcoApril 4 to April 8$432
JFKSantiago de los CaballerosApril 5 to April 25$488
JFKSantiago de los CaballerosApril 5 to April 25$488
MIAWest EndApril 5 to April 12$523
JFKSanto DomingoApril 4 to April 7$523
JFKOranjestadApril 5 to April 9$526
JFKPiarcoApril 5 to April 10$580
EWRMontego BayApril 4 to April 8$656
EWRMontego BayApril 4 to April 8$656
EWRKingstonApril 5 to April 8$724
*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
Sunset at the Palms Resort - Adults Only - All Inclusive
Hotel Riu Palace Paradise Island - 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 Condado Beach are located nearby.
9/10 Wonderful! (1,000 reviews)
Staff was helpful, place beautiful

Reviewed on Mar 27, 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 6 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.
8.6/10 Excellent! (2,423 reviews)
Excellent location

Reviewed on Apr 1, 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 Condado Beach are located nearby.
9/10 Wonderful! (1,605 reviews)
The whole elevator scanning the key card situation was a disaster for us and most guests we encountered. We stayed for two nights and the second night our a/c stopped working. The staff didn’t care, nor did they try to fix it. The hot tub was not working during our stay The rooms are, otherwise, ...

Reviewed on Apr 1, 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 Junkanoo Beach and Cable Beach are located nearby.
9/10 Wonderful! (1,458 reviews)
Yes it was a very great stay loved it. We rented a side x side and kept it outside. I loved thatjust to be able to do whatever. The resort is huge but it isnt a bad walk anywhere its is layed out very well. Overall the best spring break we have had.

Reviewed on Mar 29, 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 $112. 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 20 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 $112. 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 $112 and $724 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.