$96 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.

10:18 am - 1:16 pm

MCO

SJU

2h 58mnonstop

6:05 am - 9:13 am

SJU

MCO

3h 08mnonstop

$231Frontier

Wed, Oct 21 - Wed, Oct 28

6:55 am - 3:19 pm

MCO

SJU

8h 24m

1 stop

6:42 pm - 9:52 pm

SJU

MCO

3h 10mnonstop

$232Frontier

Fri, Sep 18 - Mon, Sep 21

8:00 pm - 12:13 am

JFK

SJU

4h 13mnonstop

5:01 am - 8:54 am

SJU

JFK

3h 53mnonstop

$282JetBlue

Mon, Jul 20 - Tue, Aug 4

5:29 pm - 9:39 pm

JFK

SJU

4h 10mnonstop

5:01 am - 8:54 am

SJU

JFK

3h 53mnonstop

$284JetBlue

Mon, Aug 17 - Tue, Aug 18

8:59 am - 6:33 pm

JFK

SJU

9h 34m

2 stops

7:24 pm - 1:28 pm

SJU

JFK

18h 04m

1 stop

$286American Airlines

Tue, Aug 25 - Tue, Sep 1

1:33 pm - 11:59 pm

EWR

SJU

10h 26m

1 stop

7:24 pm - 11:30 am

SJU

EWR

16h 06m

1 stop

$286American Airlines

Thu, Sep 3 - Tue, Sep 8

8:00 am - 11:57 am

EWR

SJU

3h 57mnonstop

1:00 am - 5:04 am

SJU

EWR

4h 04mnonstop

$287United Airlines

Wed, Aug 19 - Sat, Aug 29

9:47 am - 1:45 pm

EWR

SJU

3h 58mnonstop

1:00 am - 5:04 am

SJU

EWR

4h 04mnonstop

$293United Airlines

Wed, Aug 19 - Sun, Aug 23

12:40 pm - 4:33 pm

JFK

SJU

3h 53mnonstop

7:30 am - 11:25 am

SJU

JFK

3h 55mnonstop

$295Delta

Fri, Aug 21 - Wed, Aug 26

8:00 am - 12:45 pm

JFK

AUA

4h 45mnonstop

1:55 pm - 7:05 pm

AUA

JFK

5h 10mnonstop

$370Delta

Tue, Sep 29 - Tue, Oct 6

Fly from

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Wed 10/21

10:18 am-1:16 pm

Nonstop2h 58m

San Juan Luis Munoz Marin Intl

Wed 10/28

6:05 am-9:13 am

Nonstop3h 08m

$231

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Fri 9/18

6:55 am-3:19 pm

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Mon 9/21

6:42 pm-9:52 pm

Nonstop3h 10m

$232

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 7/20

8:00 pm-12:13 am

Nonstop4h 13m

San Juan Luis Munoz Marin Intl

Tue 8/4

5:01 am-8:54 am

Nonstop3h 53m

$282

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 8/17

5:29 pm-9:39 pm

Nonstop4h 10m

San Juan Luis Munoz Marin Intl

Tue 8/18

5:01 am-8:54 am

Nonstop3h 53m

$284

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 8/25

8:59 am-6:33 pm

2 stops9h 34m

San Juan Luis Munoz Marin Intl

Tue 9/1

7:24 pm-1:28 pm

1 stop18h 04m

$286

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Thu 9/3

1:33 pm-11:59 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Tue 9/8

7:24 pm-11:30 am

1 stop16h 06m

$286

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Wed 8/19

8:00 am-11:57 am

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Sat 8/29

1:00 am-5:04 am

Nonstop4h 04m

$287

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Wed 8/19

9:47 am-1:45 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Sun 8/23

1:00 am-5:04 am

Nonstop4h 04m

$293

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 8/21

12:40 pm-4:33 pm

Nonstop3h 53m

San Juan Luis Munoz Marin Intl

Wed 8/26

7:30 am-11:25 am

Nonstop3h 55m

$295

New YorkOranjestad

JFK - AUA

JFKAUA

New York John F Kennedy Intl

Tue 9/29

8:00 am-12:45 pm

Nonstop4h 45m

Oranjestad Reina Beatrix

Tue 10/6

1:55 pm-7:05 pm

Nonstop5h 10m

$370

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	$679 - $1,081

CHEAPEST COUNTRY	Jamaica	18% cheaper	Users typically spent $148 less on flights to Jamaica
MOST EXPENSIVE COUNTRY	Trinidad and Tobago	31% more expensive	Users typically spent $254 more on trips to Trinidad and Tobago
MOST POPULAR COUNTRY TO FLY TO	Puerto Rico	259% 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 87% less than the continental average.

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

Castries

Flights to Caribbean are typically 70% more expensive when flying to Castries, where the average price is $611

Cheap Caribbean flight deals and tips

Summary info about Caribbean flight prices, duration and airlines

Best One-Way Price	$96
Best Round-Trip Price	$231
Fastest flight time	3h 57m
Popular in	December

The best one-way flight price to Caribbean from United States in the last 5 days is $96 (Newark to Oranjestad Reina Beatrix).

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The best round-trip flight price to Caribbean from United States in the last 5 days is $231 (Orlando to San Juan Luis Munoz Marin Intl).

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The fastest flight to Caribbean from United States takes 3h 57m (New York John F Kennedy Intl to Punta Cana).

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December has the highest demand for flights to Caribbean, with a 2% 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 San Juan Luis Munoz Marin Intl airport in San Juan for the best deals, with an average airfare of $86. Alternatively, Nassau Intl airport in Nassau is a close second for cheapest flights to Caribbean with an average airfare of $92.

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 June 2026, there are 69 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.