$81 Cheap Flights to Caribbean in 2025/26

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Find the cheapest flights from the United States to Caribbean

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Recent round-trip flight deals from the United States to Caribbean

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11:20 am - 4:14 pm

JFK

SJU

3h 54mnonstop

8:15 am - 11:18 am

SJU

JFK

4h 03mnonstop

$148Multiple Airlines

Wed, Jan 7 - Wed, Jan 14

12:40 pm - 5:35 pm

LGA

SJU

3h 55mnonstop

4:35 pm - 11:15 pm

SJU

LGA

7h 40m1 stop

$148Frontier

Sat, Jan 10 - Wed, Jan 14

1:55 pm - 6:55 pm

EWR

SJU

4h 00mnonstop

5:50 pm - 9:05 pm

SJU

EWR

4h 15mnonstop

$172Spirit Airlines

Sun, Jan 4 - Fri, Jan 16

11:22 am - 4:22 pm

EWR

SJU

4h 00mnonstop

6:00 am - 1:03 pm

SJU

EWR

8h 03m1 stop

$173Spirit Airlines

Wed, Jan 14 - Wed, Jan 21

7:45 am - 6:05 pm

ORD

SJU

8h 20m1 stop

1:30 pm - 7:45 pm

SJU

ORD

8h 15m1 stop

$196JetBlue

Thu, Jan 29 - Sat, Feb 7

12:41 pm - 11:44 pm

ORD

SJU

9h 03m1 stop

5:10 am - 11:48 am

SJU

ORD

8h 38m1 stop

$202JetBlue

Fri, Feb 27 - Mon, Mar 2

7:29 pm - 4:33 pm

JFK

PUJ

20h 04m1 stop

6:02 pm - 3:21 pm

PUJ

JFK

22h 19m1 stop

$282American Airlines

Thu, Jan 22 - Mon, Feb 2

5:30 am - 2:55 pm

JFK

PUJ

8h 25m1 stop

3:55 pm - 1:39 pm

PUJ

JFK

22h 44m1 stop

$283American Airlines

Tue, Jan 27 - Sat, Jan 31

11:25 am - 4:21 pm

JFK

PUJ

3h 56mnonstop

5:46 pm - 8:59 pm

PUJ

JFK

4h 13mnonstop

$287Delta

Tue, Feb 3 - Fri, Feb 6

7:30 pm - 12:32 am

JFK

SDQ

4h 02mnonstop

7:00 pm - 11:05 pm

SDQ

JFK

4h 05mnonstop

$327Delta

Wed, Feb 25 - Wed, Mar 18

Fly from

Route

Depart

Return

Price

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 1/7

11:20 am-4:14 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Wed 1/14

8:15 am-11:18 am

Nonstop4h 03m

$148

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Sat 1/10

12:40 pm-5:35 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Wed 1/14

4:35 pm-11:15 pm

1 stop7h 40m

$148

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sun 1/4

1:55 pm-6:55 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Fri 1/16

5:50 pm-9:05 pm

Nonstop4h 15m

$172

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Wed 1/14

11:22 am-4:22 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Wed 1/21

6:00 am-1:03 pm

1 stop8h 03m

$173

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 1/29

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Sat 2/7

1:30 pm-7:45 pm

1 stop8h 15m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:10 am-11:48 am

1 stop8h 38m

$202

New YorkPunta Cana

JFK - PUJ

JFKPUJ

New York John F Kennedy Intl

Thu 1/22

7:29 pm-4:33 pm

1 stop20h 04m

Punta Cana

Mon 2/2

6:02 pm-3:21 pm

1 stop22h 19m

$282

New YorkPunta Cana

JFK - PUJ

JFKPUJ

New York John F Kennedy Intl

Tue 1/27

5:30 am-2:55 pm

1 stop8h 25m

Punta Cana

Sat 1/31

3:55 pm-1:39 pm

1 stop22h 44m

$283

New YorkPunta Cana

JFK - PUJ

JFKPUJ

New York John F Kennedy Intl

Tue 2/3

11:25 am-4:21 pm

Nonstop3h 56m

Punta Cana

Fri 2/6

5:46 pm-8:59 pm

Nonstop4h 13m

$287

New YorkSanto Domingo

JFK - SDQ

JFKSDQ

New York John F Kennedy Intl

Wed 2/25

7:30 pm-12:32 am

Nonstop4h 02m

Santo Domingo Las Americas

Wed 3/18

7:00 pm-11:05 pm

Nonstop4h 05m

$327

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

Flight prices to countries in Caribbean

Interested in flights to Caribbean? Find the countries in Caribbean that you can fly to for the biggest bang for your buck

	Price	$558 - $1,069

CHEAPEST COUNTRY	Cayman Islands	22% cheaper	Users typically spent $153 less on flights to Cayman Islands
MOST EXPENSIVE COUNTRY	Trinidad and Tobago	50% more expensive	Users typically spent $358 more on trips to Trinidad and Tobago
MOST POPULAR COUNTRY TO FLY TO	Puerto Rico	331% more popular	As a popular travel destination, more of our users plan to visit Puerto Rico than any other country in Caribbean

Where are the most popular flight destinations in Caribbean?

The most popular flight destination in Caribbean, according to our users, is Dominican Republic, followed by Jamaica, The Bahamas, Cuba and Puerto Rico.

Cheapest flights to cities in Caribbean

Click on the cities below to find out when it's cheapest to fly to Caribbean from United States

San Juan Luis Munoz Marin Intl Airport

Caribbean

Cheapest flight to Caribbean from San Juan Luis Munoz Marin Intl Airport

Christiansted

When booking a flight to Caribbean, the best-priced flight will typically be to Christiansted for $84, which is 85% less than the continental average.

Most expensive flight to Caribbean from San Juan Luis Munoz Marin Intl Airport

Pointe-à-Pitre

Flights to Caribbean are typically 59% more expensive when flying to Pointe-à-Pitre, where the average price is $537

Cheap Caribbean flight deals and tips

Summary info about Caribbean flight prices, duration and airlines

Best One-Way Price	$81
Best Round-Trip Price	$148
Fastest flight time	3h 51m
Popular in	December

The best one-way flight price to Caribbean from United States in the last 72 hours is $81 (Newark to San Juan Luis Munoz Marin Intl).

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The best round-trip flight price to Caribbean from United States in the last 72 hours is $148 (New York John F Kennedy Intl to San Juan Luis Munoz Marin Intl).

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The fastest flight to Caribbean from United States takes 3h 51m (New York John F Kennedy Intl to Santiago de los Caballeros).

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December has the highest demand for flights to Caribbean, with a 5% price increase on average.

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Frequently asked questions about flying to Caribbean

Where is it cheapest to fly into Caribbean?

If you're headed to Caribbean, consider flying into George Town Owen Roberts Intl airport in George Town for the best deals, with an average airfare of $50. Alternatively, Simpson Bay Princess Juliana airport in Simpson Bay is a close second for cheapest flights to Caribbean with an average airfare of $53.

When did momondo last update prices for flights to Caribbean?

Prices for flights to Caribbean are refreshed on a daily basis.

How many operators does momondo search for flights to Caribbean?

As of December 2025, there are 72 operators available to choose from for flights to Caribbean.

How old do you have to be to fly to Caribbean?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal to Caribbean?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights to Caribbean. Millions of users trust and use momondo every year so you are in good company.

Can I find flights to Caribbean with flexible booking policies on momondo?

Flights to Caribbean with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights to Caribbean?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight to Caribbean.

I’m not ready to book a flight to Caribbean right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Caribbean. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Caribbean trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

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Find better results for your trip to Caribbean

$81 Cheap flights to Caribbean

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Caribbean departing on 3/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from the United States to Caribbean

Recent round-trip flight deals from the United States to Caribbean

Recent one-way flight deals from the United States to Caribbean

Recent last minute flight deals from the United States to Caribbean

Recent direct flight deals from the United States to Caribbean

momondo Fare Finder

Use the filters below to find and compare flights to Caribbean that are best for you.

Flight prices to countries in Caribbean

Interested in flights to Caribbean? Find the countries in Caribbean that you can fly to for the biggest bang for your buck

Where are the most popular flight destinations in Caribbean?

The most popular flight destination in Caribbean, according to our users, is Dominican Republic, followed by Jamaica, The Bahamas, Cuba and Puerto Rico.

Cheapest flights to cities in Caribbean

Click on the cities below to find out when it's cheapest to fly to Caribbean from United States

Cheap Caribbean flight deals and tips

Summary info about Caribbean flight prices, duration and airlines

Best One-Way Price

Best Round-Trip Price

Fastest flight time

Popular in

Frequently asked questions about flying to Caribbean

Where is it cheapest to fly into Caribbean?

When did momondo last update prices for flights to Caribbean?

How many operators does momondo search for flights to Caribbean?

How old do you have to be to fly to Caribbean?

What documentation or ID do you need to fly to Caribbean?

Why use momondo?

Why should I use momondo to find a flight deal to Caribbean?

Can I find flights to Caribbean with flexible booking policies on momondo?

How can momondo help me find flights to Caribbean?

I’m not ready to book a flight to Caribbean right now. Can momondo alert me if prices change?

An easier way to manage your Caribbean trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean

Popular flights to Caribbean

Popular routes according to searches in the past day on momondo