$92 Cheap Flights to Caribbean in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

8:54 pm - 6:44 am

MCO

SJU

9h 50m

1 stop

3:36 pm - 11:59 pm

SJU

MCO

8h 23m

1 stop

$199Frontier

Sat, Aug 15 - Mon, Aug 17

11:59 pm - 4:01 am

PHL

SJU

4h 02mnonstop

2:36 pm - 6:42 pm

SJU

PHL

4h 06mnonstop

$208Frontier

Tue, Jun 2 - Tue, Jun 9

5:14 pm - 11:07 pm

ORD

SJU

4h 53mnonstop

7:14 pm - 9:00 am

SJU

ORD

14h 46m

1 stop

$222American Airlines

Sun, Aug 23 - Wed, Aug 26

6:40 am - 4:37 pm

ORD

SJU

8h 57m

1 stop

5:45 pm - 11:57 pm

SJU

ORD

7h 12m

1 stop

$226Delta

Wed, Aug 19 - Wed, Sep 2

5:14 pm - 11:07 pm

ORD

SJU

4h 53mnonstop

7:14 pm - 9:00 am

SJU

ORD

14h 46m

1 stop

$227American Airlines

Wed, Aug 19 - Wed, Aug 26

1:48 pm - 10:29 pm

ORD

SJU

7h 41m

1 stop

7:00 am - 5:41 pm

SJU

ORD

11h 41m

1 stop

$236Delta

Sat, Aug 22 - Tue, Sep 1

8:30 pm - 12:35 am

EWR

SJU

4h 05mnonstop

6:00 am - 9:59 am

SJU

EWR

3h 59mnonstop

$242JetBlue

Mon, Jun 8 - Wed, Jun 17

8:30 pm - 12:35 am

EWR

SJU

4h 05mnonstop

8:41 am - 12:45 pm

SJU

EWR

4h 04mnonstop

$252JetBlue

Mon, Jun 1 - Thu, Jun 4

7:45 pm - 11:50 pm

EWR

SJU

4h 05mnonstop

1:00 am - 5:10 am

SJU

EWR

4h 10mnonstop

$257United Airlines

Mon, Jun 1 - Wed, Jun 3

6:00 am - 12:40 pm

EWR

AUA

6h 40m

1 stop

5:50 pm - 10:47 pm

AUA

EWR

4h 57mnonstop

$361United Airlines

Mon, Jun 1 - Thu, Jun 4

Fly from

Route

Depart

Return

Price

Cheapest round-trip

OrlandoSan Juan

MCO - SJU

MCOSJU

Orlando

Sat 8/15

8:54 pm-6:44 am

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Mon 8/17

3:36 pm-11:59 pm

1 stop8h 23m

$199

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Tue 6/2

11:59 pm-4:01 am

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Tue 6/9

2:36 pm-6:42 pm

Nonstop4h 06m

$208

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/23

5:14 pm-11:07 pm

Nonstop4h 53m

San Juan Luis Munoz Marin Intl

Wed 8/26

7:14 pm-9:00 am

1 stop14h 46m

$222

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 8/19

6:40 am-4:37 pm

1 stop8h 57m

San Juan Luis Munoz Marin Intl

Wed 9/2

5:45 pm-11:57 pm

1 stop7h 12m

$226

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 8/19

5:14 pm-11:07 pm

Nonstop4h 53m

San Juan Luis Munoz Marin Intl

Wed 8/26

7:14 pm-9:00 am

1 stop14h 46m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/22

1:48 pm-10:29 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Tue 9/1

7:00 am-5:41 pm

1 stop11h 41m

$236

Quickest round-trip

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 6/8

8:30 pm-12:35 am

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Wed 6/17

6:00 am-9:59 am

Nonstop3h 59m

$242

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 6/1

8:30 pm-12:35 am

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Thu 6/4

8:41 am-12:45 pm

Nonstop4h 04m

$252

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 6/1

7:45 pm-11:50 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Wed 6/3

1:00 am-5:10 am

Nonstop4h 10m

$257

NewarkOranjestad

EWR - AUA

EWRAUA

Newark

Mon 6/1

6:00 am-12:40 pm

1 stop6h 40m

Oranjestad Reina Beatrix

Thu 6/4

5:50 pm-10:47 pm

Nonstop4h 57m

$361

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	$690 - $1,117

CHEAPEST COUNTRY	Aruba	17% cheaper	Users typically spent $140 less on flights to Aruba
MOST EXPENSIVE COUNTRY	Trinidad and Tobago	35% more expensive	Users typically spent $287 more on trips to Trinidad and Tobago
MOST POPULAR COUNTRY TO FLY TO	Puerto Rico	311% 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 $608

Cheap Caribbean flight deals and tips

Summary info about Caribbean flight prices, duration and airlines

Best One-Way Price	$93
Best Round-Trip Price	$199
Fastest flight time	3h 05m
Popular in	December

The best one-way flight price to Caribbean from United States in the last 72 hours is $93 (Philadelphia to San Juan Luis Munoz Marin Intl).

Search Deals

The best round-trip flight price to Caribbean from United States in the last 72 hours is $199 (Orlando to San Juan Luis Munoz Marin Intl).

Search Deals

The fastest flight to Caribbean from United States takes 3h 05m (Orlando to San Juan Luis Munoz Marin Intl).

Search Deals

December has the highest demand for flights to Caribbean, with a 3% price increase on average.

Search Deals

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 $55. Alternatively, San Juan Luis Munoz Marin Intl airport in San Juan is a close second for cheapest flights to Caribbean with an average airfare of $55.

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 May 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.