$89 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.

1:44 pm - 4:49 pm

MCO

SJU

3h 05mnonstop

6:09 pm - 9:21 pm

SJU

MCO

3h 12mnonstop

$195Frontier

Thu, Aug 27 - Mon, Aug 31

11:17 pm - 2:15 am

MCO

SJU

2h 58mnonstop

12:11 pm - 3:25 pm

SJU

MCO

3h 14mnonstop

$195Frontier

Sat, Aug 29 - Sat, Sep 5

6:24 pm - 11:20 pm

MCO

SJU

4h 56m

1 stop

5:00 pm - 10:16 pm

SJU

MCO

5h 16m

1 stop

$197JetBlue

Sun, Aug 23 - Wed, Aug 26

6:24 pm - 11:20 pm

MCO

SJU

4h 56m

1 stop

5:05 am - 11:02 am

SJU

MCO

5h 57m

1 stop

$197JetBlue

Wed, Aug 19 - Sun, Aug 23

6:00 am - 9:55 pm

MCO

SJU

15h 55m

1 stop

6:00 am - 9:02 pm

SJU

MCO

15h 02m

1 stop

$211American Airlines

Tue, Aug 25 - Wed, Aug 26

9:10 am - 9:55 pm

MCO

SJU

12h 45m

1 stop

6:00 am - 7:28 pm

SJU

MCO

13h 28m

1 stop

$211American Airlines

Sun, Aug 23 - Mon, Aug 24

7:20 am - 11:04 am

PHL

SJU

3h 44mnonstop

5:12 pm - 12:32 pm

SJU

PHL

19h 20m

2 stops

$216Multiple Airlines

Tue, Oct 20 - Wed, Oct 28

11:23 am - 3:19 pm

PHL

SJU

3h 56mnonstop

5:12 pm - 7:24 pm

SJU

PHL

26h 12m

2 stops

$216Multiple Airlines

Sat, Oct 10 - Thu, Oct 15

6:00 am - 2:00 pm

PHL

SJU

7h 00m

1 stop

3:10 pm - 11:15 pm

SJU

PHL

9h 05m

1 stop

$226Delta

Sun, Nov 15 - Wed, Nov 18

5:15 am - 5:25 pm

PHL

SJU

11h 10m

1 stop

3:35 pm - 10:24 pm

SJU

PHL

7h 49m

1 stop

$226Delta

Mon, Nov 9 - Fri, Nov 13

Fly from

Route

Depart

Return

Price

Cheapest round-trip

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Thu 8/27

1:44 pm-4:49 pm

Nonstop3h 05m

San Juan Luis Munoz Marin Intl

Mon 8/31

6:09 pm-9:21 pm

Nonstop3h 12m

$195

Quickest round-trip

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Sat 8/29

11:17 pm-2:15 am

Nonstop2h 58m

San Juan Luis Munoz Marin Intl

Sat 9/5

12:11 pm-3:25 pm

Nonstop3h 14m

$195

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Sun 8/23

6:24 pm-11:20 pm

1 stop4h 56m

San Juan Luis Munoz Marin Intl

Wed 8/26

5:00 pm-10:16 pm

1 stop5h 16m

$197

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Wed 8/19

6:24 pm-11:20 pm

1 stop4h 56m

San Juan Luis Munoz Marin Intl

Sun 8/23

5:05 am-11:02 am

1 stop5h 57m

$197

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Tue 8/25

6:00 am-9:55 pm

1 stop15h 55m

San Juan Luis Munoz Marin Intl

Wed 8/26

6:00 am-9:02 pm

1 stop15h 02m

$211

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Sun 8/23

9:10 am-9:55 pm

1 stop12h 45m

San Juan Luis Munoz Marin Intl

Mon 8/24

6:00 am-7:28 pm

1 stop13h 28m

$211

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Tue 10/20

7:20 am-11:04 am

Nonstop3h 44m

San Juan Luis Munoz Marin Intl

Wed 10/28

5:12 pm-12:32 pm

2 stops19h 20m

$216

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sat 10/10

11:23 am-3:19 pm

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Thu 10/15

5:12 pm-7:24 pm

2 stops26h 12m

$216

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sun 11/15

6:00 am-2:00 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Wed 11/18

3:10 pm-11:15 pm

1 stop9h 05m

$226

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 11/9

5:15 am-5:25 pm

1 stop11h 10m

San Juan Luis Munoz Marin Intl

Fri 11/13

3:35 pm-10:24 pm

1 stop7h 49m

$226

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	$665 - $1,210

CHEAPEST COUNTRY	Jamaica	19% cheaper	Users typically spent $155 less on flights to Jamaica
MOST EXPENSIVE COUNTRY	Trinidad and Tobago	48% more expensive	Users typically spent $390 more on trips to Trinidad and Tobago
MOST POPULAR COUNTRY TO FLY TO	Puerto Rico	278% 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 86% 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 $600

Cheap Caribbean flight deals and tips

Summary info about Caribbean flight prices, duration and airlines

Best One-Way Price	$89
Best Round-Trip Price	$195
Fastest flight time	3h 45m
Popular in	December

The best one-way flight price to Caribbean from United States in the last 5 days is $89 (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 5 days is $195 (Orlando to San Juan Luis Munoz Marin Intl).

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The fastest flight to Caribbean from United States takes 3h 45m (Newark to Santiago de los Caballeros).

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December has the highest demand for flights to Caribbean, with a 1% 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 $53. Alternatively, Nassau Intl airport in Nassau is a close second for cheapest flights to Caribbean with an average airfare of $82.

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 July 2026, there are 68 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.