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*
EWRSan JuanApril 28 to April 29$182
EWRMontego BayMay 5 to May 13$264
EWRSanto DomingoApril 21 to April 22$269
JFKSan JuanApril 22 to April 23$295
EWRPunta CanaMay 10 to May 14$306
EWRPiarcoJuly 8 to July 16$335
JFKSanto DomingoApril 24 to April 25$348
JFKNassauApril 25 to April 29$351
JFKPunta CanaMay 11 to May 15$355
JFKOranjestadMay 3 to May 7$357
LGASantiago de los CaballerosApril 19 to April 23$361
EWRNassauMay 6 to May 13$363
JFKSantiago de los CaballerosMay 10 to May 10$378
JFKWest EndMay 1 to May 5$473
JFKWest EndMay 1 to May 5$473
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
EWRSan JuanApril 10 to April 17$194
EWRSan JuanApril 10 to April 17$194
LGASanto DomingoApril 11 to April 13$321
JFKMontego BayApril 11 to April 18$339
JFKMontego BayApril 11 to April 18$339
JFKNassauApril 11 to April 14$370
EWRPunta CanaApril 12 to April 15$382
EWRPiarcoApril 10 to April 13$407
EWRPiarcoApril 10 to April 13$407
LGASantiago de los CaballerosApril 12 to April 20$413
EWRSantiago de los CaballerosApril 12 to April 20$437
JFKSantiago de los CaballerosApril 11 to April 14$458
JFKSanto DomingoApril 10 to April 17$489
EWRKingstonApril 12 to April 20$540
JFKKingstonApril 11 to April 19$653
*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
Ocho Rios Villa at the Palms V
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! (2,427 reviews)
The staff was the most humbling people ever. Our rooms had towels supplies at our disposal for the most part. That’s important. Convenient location for everything. Thanks British Colonial for an amazing stay. Bravo.

Reviewed on Apr 2, 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! (1,607 reviews)
Room mix up after checking in caused quite a delay. Nowhere near enough staff available to handle the check in lines.

Reviewed on Apr 2, 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! (1,459 reviews)
Great resort

Reviewed on Apr 2, 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 $653 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.