$81 Cheap Flights to Caribbean in 2026

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Find the cheapest flights from the United States to Caribbean

Round-trip

One-way

Last minute

Direct

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

Enter your travel dates to find the best prices.

5:35 am - 12:25 am

PHL

SJU

18h 50m

1 stop

3:23 pm - 12:54 am

SJU

PHL

9h 31m

1 stop

$159Frontier

Fri, Apr 10 - Fri, Apr 17

8:39 pm - 12:29 am

PHL

SJU

3h 50mnonstop

6:30 am - 10:41 am

SJU

PHL

4h 11mnonstop

$168Frontier

Sun, May 3 - Sun, May 10

8:18 am - 6:55 pm

PHL

SJU

10h 37m

1 stop

2:09 am - 6:12 am

SJU

PHL

4h 03mnonstop

$169Spirit Airlines

Tue, Apr 14 - Sat, Apr 18

8:39 pm - 12:29 am

PHL

SJU

3h 50mnonstop

3:23 pm - 12:54 am

SJU

PHL

9h 31m

1 stop

$172Frontier

Fri, Apr 10 - Fri, Apr 17

6:01 pm - 1:17 am

PHL

SJU

7h 16m

1 stop

6:00 am - 1:59 pm

SJU

PHL

7h 59m

1 stop

$175Frontier

Sun, Apr 12 - Thu, Apr 16

6:10 pm - 11:49 am

ORD

SJU

16h 39m

1 stop

10:59 am - 3:08 pm

SJU

ORD

5h 09mnonstop

$202Spirit Airlines

Sun, Apr 12 - Wed, Apr 15

5:50 am - 7:50 pm

EWR

SJU

14h 00m

1 stop

3:08 am - 12:59 pm

SJU

EWR

9h 51m

1 stop

$202Multiple Airlines

Tue, Apr 14 - Tue, Apr 21

5:05 am - 6:55 pm

ORD

SJU

12h 50m

1 stop

3:31 pm - 11:44 pm

SJU

ORD

9h 13m

1 stop

$208Multiple Airlines

Mon, Apr 13 - Thu, Apr 16

9:59 pm - 9:58 am

JFK

PUJ

11h 59m

1 stop

7:20 pm - 11:22 pm

PUJ

JFK

4h 02mnonstop

$319JetBlue

Mon, Apr 20 - Tue, Apr 21

10:55 am - 2:49 pm

JFK

PUJ

3h 54mnonstop

5:13 pm - 1:56 am

PUJ

JFK

8h 43m

1 stop

$321JetBlue

Tue, May 19 - Tue, May 19

Fly from

Route

Depart

Return

Price

Cheapest round-trip

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Fri 4/10

5:35 am-12:25 am

1 stop18h 50m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-12:54 am

1 stop9h 31m

$159

Quickest round-trip

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sun 5/3

8:39 pm-12:29 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sun 5/10

6:30 am-10:41 am

Nonstop4h 11m

$168

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Tue 4/14

8:18 am-6:55 pm

1 stop10h 37m

San Juan Luis Munoz Marin Intl

Sat 4/18

2:09 am-6:12 am

Nonstop4h 03m

$169

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Fri 4/10

8:39 pm-12:29 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-12:54 am

1 stop9h 31m

$172

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sun 4/12

6:01 pm-1:17 am

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Thu 4/16

6:00 am-1:59 pm

1 stop7h 59m

$175

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 4/12

6:10 pm-11:49 am

1 stop16h 39m

San Juan Luis Munoz Marin Intl

Wed 4/15

10:59 am-3:08 pm

Nonstop5h 09m

$202

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 4/14

5:50 am-7:50 pm

1 stop14h 00m

San Juan Luis Munoz Marin Intl

Tue 4/21

3:08 am-12:59 pm

1 stop9h 51m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 4/13

5:05 am-6:55 pm

1 stop12h 50m

San Juan Luis Munoz Marin Intl

Thu 4/16

3:31 pm-11:44 pm

1 stop9h 13m

$208

New YorkPunta Cana

JFK - PUJ

JFKPUJ

New York John F Kennedy Intl

Mon 4/20

9:59 pm-9:58 am

1 stop11h 59m

Punta Cana

Tue 4/21

7:20 pm-11:22 pm

Nonstop4h 02m

$319

New YorkPunta Cana

JFK - PUJ

JFKPUJ

New York John F Kennedy Intl

Tue 5/19

10:55 am-2:49 pm

Nonstop3h 54m

Punta Cana

Tue 5/19

5:13 pm-1:56 am

1 stop8h 43m

$321

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	$568 - $965

CHEAPEST COUNTRY	Turks and Caicos Islands	23% cheaper	Users typically spent $174 less on flights to Turks and Caicos Islands
MOST EXPENSIVE COUNTRY	Trinidad and Tobago	30% more expensive	Users typically spent $224 more on trips to Trinidad and Tobago
MOST POPULAR COUNTRY TO FLY TO	Puerto Rico	318% 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 61% more expensive when flying to Pointe-à-Pitre, where the average price is $553

Cheap Caribbean flight deals and tips

Summary info about Caribbean flight prices, duration and airlines

Best One-Way Price	$81
Best Round-Trip Price	$159
Fastest flight time	3h 48m
Popular in	December

The best one-way flight price to Caribbean from United States in the last 72 hours is $81 (Philadelphia 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 $159 (Philadelphia to San Juan Luis Munoz Marin Intl).

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The fastest flight to Caribbean from United States takes 3h 48m (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 Aguadilla Borinquen airport in Aguadilla for the best deals, with an average airfare of $45. Alternatively, Simpson Bay Princess Juliana airport in Simpson Bay is a close second for cheapest flights to Caribbean with an average airfare of $46.

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 March 2026, there are 65 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.