Cheap Flights to Caribbean from $58 (2025/2026)

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Jet to one of Caribbean's top cities

Dominican Republic which includes a sunset and general coastal views

Santo Domingo

Flights
Santo Domingo

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.

Wed, Dec 10 - Fri, Dec 19
EWR
Newark Liberty Intl. Airport
SJU
Luis Munoz Marin Intl.
$107 Roundtrip, just found
$107
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Dec 10 from Newark Liberty Intl. Airport to Luis Munoz Marin Intl., returning Fri, Dec 19, priced at $107 just found
Tue, Feb 24 - Wed, Mar 4
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$116 Roundtrip, just found
$116
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Feb 24 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Wed, Mar 4, priced at $116 just found
Mon, Dec 8 - Sat, Mar 14
EWR
Newark Liberty Intl. Airport
PUJ
Punta Cana Intl.
$236 Roundtrip, found 1 day ago
$236
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Dec 8 from Newark Liberty Intl. Airport to Punta Cana Intl., returning Sat, Mar 14, priced at $236 found 1 day ago
Sat, Jan 10 - Sat, Jan 17
EWR
Newark Liberty Intl. Airport
AUA
Queen Beatrix Intl.
$245 Roundtrip, just found
$245
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jan 10 from Newark Liberty Intl. Airport to Queen Beatrix Intl., returning Sat, Jan 17, priced at $245 just found
Sun, Mar 15 - Thu, Mar 19
EWR
Newark Liberty Intl. Airport
SDQ
Las Americas Intl.
$245 Roundtrip, just found
$245
Roundtrip
just found
Select Arajet flight, departing Sun, Mar 15 from Newark Liberty Intl. Airport to Las Americas Intl., returning Thu, Mar 19, priced at $245 just found
Tue, Apr 14 - Tue, Apr 14
JFK
John F. Kennedy Intl.
PUJ
Punta Cana Intl.
$247 Roundtrip, just found
$247
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Apr 14 from John F. Kennedy Intl. to Punta Cana Intl., returning Tue, Apr 14, priced at $247 just found
Wed, Jan 14 - Thu, Jan 15
JFK
John F. Kennedy Intl.
SDQ
Las Americas Intl.
$266 Roundtrip, found 17 hours ago
$266
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, Jan 14 from John F. Kennedy Intl. to Las Americas Intl., returning Thu, Jan 15, priced at $266 found 17 hours ago
Fri, Sep 18 - Sat, Sep 19
JFK
John F. Kennedy Intl.
STI
Cibao Intl.
$272 Roundtrip, just found
$272
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, Sep 18 from John F. Kennedy Intl. to Cibao Intl., returning Sat, Sep 19, priced at $272 just found
OriginDestinationTravel DatesFlights From*
JFKSan JuanFebruary 24 to March 4$116
EWRSanto DomingoJanuary 19 to January 29$245
EWRPunta CanaJanuary 20 to January 27$245
JFKSantiago de los CaballerosFebruary 26 to February 27$273
JFKSantiago de los CaballerosFebruary 26 to February 27$273
JFKSanto DomingoFebruary 24 to February 25$282
JFKPunta CanaJanuary 31 to February 6$283
JFKPiarcoJanuary 22 to February 1$296
EWRMontego BayJanuary 7 to January 15$296
JFKOranjestadJanuary 6 to January 12$302
EWRNassauJanuary 12 to January 23$315
JFKMontego BayJanuary 1 to January 19$325
JFKKingstonJanuary 9 to January 15$392
JFKWest EndJanuary 8 to January 14$398
JFKWest EndJanuary 8 to January 14$398
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKSan JuanDecember 6 to December 16$134
JFKSan JuanDecember 6 to December 16$134
EWRSan JuanDecember 6 to December 10$173
EWRSanto DomingoDecember 7 to December 9$299
EWRSanto DomingoDecember 7 to December 9$299
JFKPiarcoDecember 6 to December 9$309
EWRSantiago de los CaballerosDecember 7 to December 10$332
JFKSanto DomingoDecember 6 to December 7$339
LGAMontego BayDecember 7 to December 14$351
JFKOranjestadDecember 6 to December 9$358
JFKNassauDecember 5 to December 13$360
JFKMontego BayDecember 6 to December 12$362
JFKSantiago de los CaballerosDecember 6 to December 8$363
JFKPunta CanaDecember 5 to December 8$371
JFKKingstonDecember 7 to December 13$430
*Prices include taxes and fees

Best Caribbean Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Oliver Hotel
3.0-star property

The Oliver Hotel

Feb 8 - Feb 14

6 night stay

Boston (BOS) to San Juan (SJU)

Spirit Airlines • Coach

San Juan (SJU) to Boston (BOS)

Frontier Airlines • Coach
Price was $1,473, price is now $546 per person
$546
per person
found 2 days ago
Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

Feb 7 - Feb 14

7 night stay

Boston (BOS) to San Juan (SJU)

Spirit Airlines • Coach

San Juan (SJU) to Boston (BOS)

Frontier Airlines • Coach
Price was $2,919, price is now $1,053 per person
$1,053
per person
found 2 days ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Feb 10 - Feb 17

7 night stay

New York (JFK) to Montego Bay (MBJ)

Delta • Coach

Montego Bay (MBJ) to New York (JFK)

American Airlines • Coach
Price was $2,943, price is now $1,117 per person
$1,117
per person
found 1 day ago
Don't see what you're looking for?
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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.
8.8/10 Excellent! (1,000 reviews)
The room was very clean staff was very friendly enjoyed my stay and will go back again 😊

Reviewed on Nov 15, 2025

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! (2,044 reviews)
What stood out was the architectural structure of the hotel and how clean it was upon arrival, from the hotel grounds, lobby, restaurants, hallways, and rooms.

Reviewed on Nov 21, 2025

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! (1,332 reviews)
Our room was very clean and spacious with an excellent view.

Reviewed on Nov 29, 2025

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! (1,434 reviews)
Amazing b

Reviewed on Nov 24, 2025

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 $107. 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 December. 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 $107. 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 $107 and $430 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.