Cheap Flights to Caribbean from $62 (2026/2027)| Travelocity

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Punta Cana

Flights

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.

Sun, Apr 12 - Thu, Apr 16

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$165

Roundtrip

just found

Tue, Apr 7 - Wed, Apr 8

JFK

John F. Kennedy Intl.

SJU

Luis Munoz Marin Intl.

$211

Roundtrip

found 1 hour ago

Mon, Apr 13 - Wed, Apr 22

JFK

John F. Kennedy Intl.

SJU

Luis Munoz Marin Intl.

$236

Roundtrip

just found

Mon, Apr 13 - Thu, Apr 16

EWR

Newark Liberty Intl. Airport

MBJ

Sir Donald Sangster Intl.

$248

Roundtrip

found 3 hours ago

Tue, May 5 - Tue, May 12

EWR

Newark Liberty Intl. Airport

PUJ

Punta Cana Intl.

$251

Roundtrip

found 11 hours ago

Mon, Apr 13 - Thu, May 7

JFK

John F. Kennedy Intl.

MBJ

Sir Donald Sangster Intl.

$301

Roundtrip

found 4 hours ago

Sat, Sep 26 - Sun, Sep 27

JFK

John F. Kennedy Intl.

SJU

Luis Munoz Marin Intl.

$302

Roundtrip

found 3 days ago

Tue, Apr 7 - Tue, Apr 7

JFK

John F. Kennedy Intl.

PUJ

Punta Cana Intl.

$307

Roundtrip

found 1 day ago

Wed, Apr 29 - Sat, May 2

JFK

John F. Kennedy Intl.

SJU

Luis Munoz Marin Intl.

$307

Roundtrip

found 1 hour ago

Fri, Apr 17 - Fri, Apr 24

JFK

John F. Kennedy Intl.

SJU

Luis Munoz Marin Intl.

$316

Roundtrip

found 3 hours ago

Wed, May 20 - Wed, May 27

JFK

John F. Kennedy Intl.

POS

Piarco Intl.

$350

Roundtrip

found 3 hours ago

Origin	Destination	Travel Dates	Flights From*
LGA	San Juan	April 11 to April 18	$148
JFK	San Juan	April 13 to April 22	$236
LGA	Montego Bay	April 13 to April 16	$248
LGA	Santo Domingo	April 12 to April 21	$259
JFK	Montego Bay	April 26 to May 9	$318
EWR	Kingston	April 13 to April 22	$328
JFK	Piarco	May 20 to May 27	$350
JFK	Nassau	April 17 to April 21	$351
JFK	Oranjestad	May 4 to May 6	$355
JFK	Santo Domingo	April 27 to April 28	$371
EWR	Nassau	April 12 to April 16	$378
JFK	Santiago de los Caballeros	May 10 to May 10	$378
JFK	Kingston	May 8 to May 12	$458
JFK	West End	April 24 to April 30	$473
JFK	West End	April 24 to April 30	$473

*Prices include taxes and fees

Origin	Destination	Travel Dates	Flights From*
EWR	San Juan	April 3 to April 5	$221
EWR	San Juan	April 3 to April 5	$221
LGA	Santo Domingo	April 5 to April 13	$339
EWR	Piarco	April 4 to April 13	$433
JFK	Piarco	April 5 to April 15	$433
JFK	Santo Domingo	April 3 to April 6	$438
EWR	Montego Bay	April 4 to May 9	$445
EWR	Montego Bay	April 4 to May 9	$445
JFK	Oranjestad	April 4 to April 7	$451
JFK	Santiago de los Caballeros	April 5 to April 21	$462
JFK	Santiago de los Caballeros	April 5 to April 21	$462
EWR	Santiago de los Caballeros	April 5 to April 21	$523
JFK	Montego Bay	April 5 to April 9	$543
EWR	Kingston	April 3 to April 7	$640
EWR	Kingston	April 3 to April 7	$640

*Prices include taxes and fees

Best Caribbean Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.

3.5-star property

Silver Creek Resort

May 20 - May 25

5 night stay

Boston (BOS) to Montego Bay (MBJ)

Air Canada • Non-stop • Coach

Montego Bay (MBJ) to Boston (BOS)

American Airlines • Non-stop • Coach

$777

per person

found 1 day ago

4.5-star property

Sunset at the Palms Resort - Adults Only - All Inclusive

May 20 - May 25

5 night stay

Boston (BOS) to Montego Bay (MBJ)

Air Canada • Non-stop • Coach

Montego Bay (MBJ) to Boston (BOS)

American Airlines • Non-stop • Coach

$1,481

per person

found 1 day ago

3.5-star property

Ocho Rios Villa at Coolshade X

May 12 - May 18

6 night stay

Boston (BOS) to Montego Bay (MBJ)

Frontier Airlines • Non-stop roundtrip • Coach

$942

per person

found 1 day ago

Don't see what you're looking for?

See all available trips from Boston to Caribbean

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Travelers ❤️ These Caribbean 🏨

Hotel El Convento

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! (1,005 reviews)

Staff was helpful, place beautiful

Reviewed on Mar 27, 2026

British Colonial - Nassau

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! (2,398 reviews)

We do not have a good experience with food.

Reviewed on Mar 27, 2026

Hotel Rumbao, a Tribute Portfolio Hotel

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! (1,592 reviews)

With very few exceptions, the service in bar and restaurant were Very Poor. The location amazing, We had a beautiful suite overlooking the port. Room maintenance and quality wonderful!

Reviewed on Mar 27, 2026

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The Reef at Atlantis

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.

8.8/10 Excellent! (1,451 reviews)

Have a great time everything seems to add up though it’s very expensive in the end especially eating out

Reviewed on Mar 26, 2026

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.

More Ways To Wander Caribbean

Caribbean Hotels

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Affordable cars to get you around town

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Save more by combining flights, hotels and cars

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 $148. 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 $148. 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 $148 and $640 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.

Cheap Flights to Caribbean from $62 (2026/2027)

Travelers

Jet to one of Caribbean's top cities

Punta Cana

St. Thomas

Montego Bay

Nassau

Providenciales

How Much Does it Cost To Fly To Caribbean?

Best Caribbean Flight and Hotel Packages

Silver Creek Resort

May 20 - May 25

Boston (BOS) to Montego Bay (MBJ)

Montego Bay (MBJ) to Boston (BOS)

Sunset at the Palms Resort - Adults Only - All Inclusive

May 20 - May 25

Boston (BOS) to Montego Bay (MBJ)

Montego Bay (MBJ) to Boston (BOS)

Ocho Rios Villa at Coolshade X

May 12 - May 18

Boston (BOS) to Montego Bay (MBJ)

Travelers ❤️ These Caribbean 🏨

Hotel El Convento

British Colonial - Nassau

Hotel Rumbao, a Tribute Portfolio Hotel

The Reef at Atlantis

More Ways To Wander Caribbean

Frequently asked questions