$90 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.

11:20 am - 12:58 am

BOS

SJU

13h 38m

1 stop

5:15 pm - 7:49 am

SJU

BOS

14h 34m

1 stop

$172Multiple Airlines

Sun, Apr 26 - Thu, May 21

11:20 am - 12:58 am

BOS

SJU

13h 38m

1 stop

5:15 pm - 7:49 am

SJU

BOS

14h 34m

1 stop

$173Multiple Airlines

Mon, Apr 27 - Thu, May 21

6:00 am - 2:13 pm

BOS

SJU

8h 13m

1 stop

5:15 pm - 1:24 am

SJU

BOS

8h 09m

1 stop

$174Frontier

Mon, May 4 - Wed, May 6

6:00 am - 2:13 pm

BOS

SJU

8h 13m

1 stop

5:15 pm - 1:24 am

SJU

BOS

8h 09m

1 stop

$175Frontier

Mon, May 4 - Wed, May 6

6:00 am - 2:13 pm

BOS

SJU

8h 13m

1 stop

5:15 pm - 1:24 am

SJU

BOS

8h 09m

1 stop

$176Frontier

Mon, May 4 - Fri, May 22

8:00 pm - 12:13 am

JFK

SJU

4h 13mnonstop

9:10 pm - 1:07 am

SJU

JFK

3h 57mnonstop

$244JetBlue

Tue, Jun 30 - Tue, Jul 7

6:15 pm - 10:31 pm

JFK

SJU

4h 16mnonstop

5:01 am - 8:54 am

SJU

JFK

3h 53mnonstop

$252JetBlue

Tue, Jun 23 - Wed, Jun 24

7:25 pm - 11:43 pm

JFK

SJU

4h 18mnonstop

1:10 pm - 5:19 pm

SJU

JFK

4h 09mnonstop

$257Delta

Tue, Jun 23 - Tue, Jun 30

9:40 am - 8:51 pm

JFK

SJU

11h 11m

2 stops

7:25 am - 6:40 pm

SJU

JFK

11h 15m

1 stop

$261American Airlines

Tue, May 5 - Wed, May 6

9:40 am - 8:51 pm

JFK

SJU

11h 11m

2 stops

5:45 am - 7:10 pm

SJU

JFK

13h 25m

1 stop

$266American Airlines

Tue, May 5 - Tue, May 12

Fly from

Route

Depart

Return

Price

Cheapest round-trip

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 4/26

11:20 am-12:58 am

1 stop13h 38m

San Juan Luis Munoz Marin Intl

Thu 5/21

5:15 pm-7:49 am

1 stop14h 34m

$172

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 4/27

11:20 am-12:58 am

1 stop13h 38m

San Juan Luis Munoz Marin Intl

Thu 5/21

5:15 pm-7:49 am

1 stop14h 34m

$173

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 5/4

6:00 am-2:13 pm

1 stop8h 13m

San Juan Luis Munoz Marin Intl

Wed 5/6

5:15 pm-1:24 am

1 stop8h 09m

$174

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 5/4

6:00 am-2:13 pm

1 stop8h 13m

San Juan Luis Munoz Marin Intl

Wed 5/6

5:15 pm-1:24 am

1 stop8h 09m

$175

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 5/4

6:00 am-2:13 pm

1 stop8h 13m

San Juan Luis Munoz Marin Intl

Fri 5/22

5:15 pm-1:24 am

1 stop8h 09m

$176

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 6/30

8:00 pm-12:13 am

Nonstop4h 13m

San Juan Luis Munoz Marin Intl

Tue 7/7

9:10 pm-1:07 am

Nonstop3h 57m

$244

Quickest round-trip

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 6/23

6:15 pm-10:31 pm

Nonstop4h 16m

San Juan Luis Munoz Marin Intl

Wed 6/24

5:01 am-8:54 am

Nonstop3h 53m

$252

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 6/23

7:25 pm-11:43 pm

Nonstop4h 18m

San Juan Luis Munoz Marin Intl

Tue 6/30

1:10 pm-5:19 pm

Nonstop4h 09m

$257

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 5/5

9:40 am-8:51 pm

2 stops11h 11m

San Juan Luis Munoz Marin Intl

Wed 5/6

7:25 am-6:40 pm

1 stop11h 15m

$261

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 5/5

9:40 am-8:51 pm

2 stops11h 11m

San Juan Luis Munoz Marin Intl

Tue 5/12

5:45 am-7:10 pm

1 stop13h 25m

$266

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	$626 - $966

CHEAPEST COUNTRY	St. Maarten	16% cheaper	Users typically spent $115 less on flights to St. Maarten
MOST EXPENSIVE COUNTRY	Trinidad and Tobago	31% more expensive	Users typically spent $226 more on trips to Trinidad and Tobago
MOST POPULAR COUNTRY TO FLY TO	Puerto Rico	270% 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 62% more expensive when flying to Pointe-à-Pitre, where the average price is $543

Cheap Caribbean flight deals and tips

Summary info about Caribbean flight prices, duration and airlines

Best One-Way Price	$90
Best Round-Trip Price	$172
Fastest flight time	3h 54m
Popular in	December

The best one-way flight price to Caribbean from United States in the last 72 hours is $90 (Boston Logan Intl 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 $172 (Boston Logan Intl to San Juan Luis Munoz Marin Intl).

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The fastest flight to Caribbean from United States takes 3h 54m (Boston Logan Intl to San Juan Luis Munoz Marin Intl).

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December has the highest demand for flights to Caribbean, with a 4% 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 Simpson Bay Princess Juliana airport in Simpson Bay for the best deals, with an average airfare of $53. Alternatively, Oranjestad Reina Beatrix airport in Oranjestad is a close second for cheapest flights to Caribbean with an average airfare of $56.

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 April 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.