Cheap Flights to Caribbean from $66 (2026/2027)| Travelocity

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Dominican Republic which includes a sunset and general coastal views

Santo Domingo

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.

Wed, Jan 21 - Sat, Jan 31

JFK

John F. Kennedy Intl.

SJU

Luis Munoz Marin Intl.

$121

Roundtrip

found 1 day ago

Sun, Jan 25 - Tue, Jan 27

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$130

Roundtrip

found 1 hour ago

Sun, Jan 25 - Fri, Jan 30

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$130

Roundtrip

just found

Tue, Jan 27 - Thu, Feb 5

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$149

Roundtrip

found 3 hours ago

Tue, Mar 3 - Wed, Mar 4

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$192

Roundtrip

found 23 hours ago

Sat, Jan 31 - Sat, Feb 7

EWR

Newark Liberty Intl. Airport

AUA

Queen Beatrix Intl.

$218

Roundtrip

found 6 hours ago

Sat, Jan 31 - Thu, Feb 5

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$222

Roundtrip

found 2 hours ago

Tue, Feb 3 - Wed, Feb 11

EWR

Newark Liberty Intl. Airport

PUJ

Punta Cana Intl.

$232

Roundtrip

found 17 hours ago

Fri, May 1 - Fri, May 1

JFK

John F. Kennedy Intl.

PUJ

Punta Cana Intl.

$236

Roundtrip

found 4 days ago

Sat, Jan 24 - Thu, Feb 12

EWR

Newark Liberty Intl. Airport

PUJ

Punta Cana Intl.

$246

Roundtrip

found 1 day ago

Sat, Feb 21 - Sat, Feb 28

JFK

John F. Kennedy Intl.

NAS

Lynden Pindling Intl.

$262

Roundtrip

found 5 hours ago

Origin	Destination	Travel Dates	Flights From*
EWR	San Juan	February 3 to February 5	$152
EWR	San Juan	February 3 to February 5	$152
JFK	San Juan	February 24 to March 4	$162
EWR	Montego Bay	February 3 to February 10	$248
EWR	Santo Domingo	March 2 to March 11	$260
EWR	Santiago de los Caballeros	January 31 to February 7	$260
EWR	Nassau	February 21 to February 28	$272
EWR	Nassau	February 21 to February 28	$272
JFK	Nassau	January 31 to February 7	$289
JFK	Santiago de los Caballeros	March 16 to March 17	$294
JFK	Montego Bay	February 21 to February 28	$325
LGA	Kingston	February 2 to February 5	$354
JFK	West End	February 9 to February 11	$399
JFK	West End	February 9 to February 11	$399
JFK	Kingston	March 23 to April 1	$410

*Prices include taxes and fees

Origin	Destination	Travel Dates	Flights From*
EWR	San Juan	January 18 to January 27	$168
JFK	San Juan	January 17 to January 30	$240
LGA	Oranjestad	January 17 to January 31	$336
JFK	Oranjestad	January 17 to January 31	$343
EWR	Nassau	January 17 to January 20	$366
EWR	Nassau	January 17 to January 20	$366
LGA	Montego Bay	January 17 to January 23	$366
LGA	Santiago de los Caballeros	January 18 to February 27	$372
JFK	Santiago de los Caballeros	January 18 to January 22	$383
LGA	Punta Cana	January 18 to January 25	$426
JFK	Punta Cana	January 17 to January 20	$436
JFK	Santo Domingo	January 17 to January 24	$437
JFK	Montego Bay	January 18 to January 22	$462
JFK	Kingston	January 18 to January 27	$512
JFK	Kingston	January 18 to January 27	$512

*Prices include taxes and fees

Best Caribbean Flight and Hotel Packages

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

4.5-star property

Ola Boutique Hotel

Mar 22 - Mar 26

4 night stay

Boston (BOS) to San Juan (SJU)

Delta • Coach

San Juan (SJU) to Boston (BOS)

Spirit Airlines • Coach

$595

per person

found 1 day ago

3.0-star property

Blue Seas Two Unity Hall

Feb 18 - Feb 22

4 night stay

Boston (BOS) to Montego Bay (MBJ)

Spirit Airlines • Non-stop • Coach

Montego Bay (MBJ) to Boston (BOS)

American Airlines • Non-stop • Coach

$761

per person

found 1 day ago

3.0-star property

Alamanda Cottage at Serenity

Jan 31 - Feb 7

7 night stay

Boston (BOS) to Montego Bay (MBJ)

Frontier Airlines • Non-stop • Coach

Montego Bay (MBJ) to Boston (BOS)

Spirit Airlines • Non-stop • Coach

$1,199

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 Pan American Pier are located nearby.

9/10 Wonderful! (1,005 reviews)

Excellent service, gorgeous property, wonderful amenities, great location. Breakfast was delicious and our room was well appointed and spotless! Highly recommend the Hotel El Convento. We’ll be back!

Reviewed on Jan 9, 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 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! (2,157 reviews)

Clean room and balcony view was amazing

Reviewed on Jan 8, 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 Pan American Pier are located nearby.

9/10 Wonderful! (1,461 reviews)

Beautiful hotel

Reviewed on Jan 11, 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 Cable Beach and Aquaventure are located nearby.

8.8/10 Excellent! (1,427 reviews)

Absolutely love staying at the reef . Staff was very friendly, very helpful. It wasn’t overwhelming with people. I love the privacy that it has as well as the beach area on this side . 10/10.

Reviewed on Jan 6, 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

Find the perfect hotel after your flight

Caribbean Vacation Rentals

Great Deals on alternative accommodations

Caribbean Car Rentals

Affordable cars to get you around town

Caribbean Vacations

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 $121. 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 January. 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 $121. 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 $121 and $512 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 $66 (2026/2027)

Travelers

Jet to one of Caribbean's top cities

Santo Domingo

Punta Cana

St. Thomas

Willemstad

How Much Does it Cost To Fly To Caribbean?

Best Caribbean Flight and Hotel Packages

Ola Boutique Hotel

Mar 22 - Mar 26

Boston (BOS) to San Juan (SJU)

San Juan (SJU) to Boston (BOS)

Blue Seas Two Unity Hall

Feb 18 - Feb 22

Boston (BOS) to Montego Bay (MBJ)

Montego Bay (MBJ) to Boston (BOS)

Alamanda Cottage at Serenity

Jan 31 - Feb 7

Boston (BOS) to Montego Bay (MBJ)

Montego Bay (MBJ) to Boston (BOS)

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