HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$239+ Cheap flights from Harlingen, TX (HRL) to Caribbean Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — SJU
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Harlingen to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Harlingen to Caribbean Islands

Cheapest flights from Harlingen to Caribbean Islands
Explore the most affordable flight options available from Harlingen to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 31, 2025.

This Southwest deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:40 amHRL - SJU
2 stops11h 35mSouthwest
Wed 1/76:10 amSJU - HRL
2 stops12h 55mSouthwest
Deal found 12/29$785
This American Airlines deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:11 pmHRL - SJU
1 stop16h 48mAmerican Airlines
Wed 1/73:54 pmSJU - HRL
1 stop9h 27mAmerican Airlines
Deal found 12/29$800
This Southwest deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2812:00 pmHRL - SJU
2 stops11h 40mSouthwest
Sat 1/35:55 pmSJU - HRL
1 stop8h 00mSouthwest
Deal found 12/28$1,165
This United Airlines deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:20 pmHRL - SJU
1 stop26h 06mUnited Airlines
Sat 1/310:15 amSJU - HRL
1 stop7h 51mUnited Airlines
Deal found 12/28$1,294

Find flight deals from Harlingen to Caribbean Islands

Keep the following information in mind while searching for Harlingen to Caribbean Islands flight deals. Data was last updated December 31, 2025.

Round-trip from

$324
(United Airlines)

One-way from

$288
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$1,475
From Harlingen Valley Intl to Caribbean Islands
Search Deals
One-way flight from Harlingen Valley Intl to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 30% potential increase in price ($303 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($79 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Harlingen to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 31, 2025.
Use the filters below to find and compare flights from Harlingen to Caribbean Islands that are best for you.

Fly from

Harlingen

Fly to

Caribbean Islands

Route

Depart

Return

Price

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Tue 1/27

9:20 am-12:36 am

2 stops13h 16m

San Juan Luis Munoz Marin Intl

Mon 2/2

2:05 am-4:06 pm

2 stops16h 01m

$239

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Sun 4/26

7:00 am-3:42 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Fri 5/1

1:00 am-4:03 pm

2 stops16h 03m

$259

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Tue 5/5

12:05 pm-8:38 pm

1 stop7h 33m

San Juan Luis Munoz Marin Intl

Tue 5/5

1:00 am-4:03 pm

2 stops16h 03m

$324

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Mon 1/19

7:00 am-4:36 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Thu 1/22

8:10 am-8:01 pm

2 stops13h 51m

$336

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Mon 1/19

11:06 am-10:26 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Thu 1/22

3:54 pm-11:21 pm

1 stop9h 27m

$357

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Sun 4/26

10:47 am-11:01 pm

1 stop11h 14m

San Juan Luis Munoz Marin Intl

Sat 5/2

11:59 pm-2:17 pm

1 stop15h 18m

$357

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Mon 3/9

8:06 pm-2:11 pm

1 stop17h 05m

San Juan Luis Munoz Marin Intl

Sat 3/14

6:33 am-7:36 pm

1 stop14h 03m

$362

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

Sat 6/13

4:56 pm-10:02 am

2 stops16h 06m

Nassau Intl

Tue 6/23

2:59 pm-11:59 pm

1 stop10h 00m

$519

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

Sat 6/13

10:25 am-6:30 pm

2 stops7h 05m

Nassau Intl

Tue 6/23

8:45 am-6:00 pm

2 stops10h 15m

$554

HarlingenSantiago de los Caballeros

HRL - STI

HRLSTI

Harlingen Valley Intl

Tue 2/3

9:20 am-11:51 pm

2 stops12h 31m

Santiago de los Caballeros

Fri 2/6

4:00 pm-11:26 am

2 stops21h 26m

$672

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

Showing 1-10 of 14 results
1
2

Best time to book a flight from Harlingen to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Harlingen with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Harlingen to Caribbean Islands

What is the cheapest month to book a flight from Harlingen, Texas to Caribbean Islands?

Currently, January is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean Islands (average of $244). Flying from Harlingen, Texas to Caribbean Islands in October is currently the most expensive (average of $448). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Harlingen to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Harlingen to Caribbean Islands?

    Located just 3.7 mi from the city center, Harlingen Valley Intl (HRL) is the airport most travelers will use when flying to Caribbean Islands from Harlingen.

  • How long is the flight from Harlingen, Texas to Caribbean Islands?

    There are many flights that can get you from Harlingen, Texas to Caribbean Islands in 7h 05m. Fly via United Airlines, American Airlines, or Southwest to get the fastest option. Airlines will cover a distance of 1258 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Harlingen, Texas to Caribbean Islands?

    While some choose either Harlingen Valley Intl - Nassau Intl or Harlingen Valley Intl - Gregory Town North Eleuthera, Harlingen Valley Intl - San Juan Luis Munoz Marin Intl is the most popular route from Harlingen, Texas to Caribbean Islands.

  • Can I find deals for flights from Harlingen to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Harlingen to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Harlingen to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Harlingen to Caribbean Islands.

  • Can I find deals for business class flights from Harlingen to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Harlingen to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Harlingen, Texas to Caribbean Islands?

    Currently, January is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean Islands (average of $244). Flying from Harlingen, Texas to Caribbean Islands in October is currently the most expensive (average of $448). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Harlingen to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to Las Vegas flights
Dallas/Fort Worth to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to Cancún flights
Dallas/Fort Worth to Denver flights
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to Seattle flights
Hobby to LaGuardia flights
George Bush Intcntl to Cancún flights
Dallas/Fort Worth to Newark flights
Dallas/Fort Worth to Orlando flights
Hobby to John F Kennedy Intl flights
Dallas/Fort Worth to Los Angeles flights
Dallas/Fort Worth to Mexico City flights
Hobby to Denver flights
Hobby to Las Vegas flights
Dallas/Fort Worth to Miami flights
Dallas/Fort Worth to San Francisco flights
Dallas/Fort Worth to Sky Harbor Intl flights
Dallas/Fort Worth to Fort Lauderdale flights
George Bush Intcntl to Las Vegas flights
Hobby to Newark flights
George Bush Intcntl to Denver flights
Hobby to Cancún flights
Dallas/Fort Worth to San Diego flights
George Bush Intcntl to John F Kennedy Intl flights
Dallas/Fort Worth to Salt Lake City flights
Austin to John F Kennedy Intl flights
Hobby to Seattle flights
Dallas/Fort Worth to Cozumel flights
Hobby to Mexico City flights
Dallas/Fort Worth to Dulles Intl flights
George Bush Intcntl to Newark flights
Austin to Las Vegas flights
Love Field to Las Vegas flights
Hobby to Orlando flights
George Bush Intcntl to LaGuardia flights
George Bush Intcntl to Seattle flights
Hobby to Los Angeles flights
Austin to Newark flights
Dallas/Fort Worth to Baltimore flights
Dallas/Fort Worth to Boston flights
Dallas/Fort Worth to Honolulu flights
Dallas/Fort Worth to Atlanta flights
Dallas/Fort Worth to Santa Ana flights
George Bush Intcntl to Mexico City flights
Hobby to Miami flights
Austin to Cancún flights
San Antonio to Las Vegas flights
Hobby to Cozumel flights

Top 3 airlines flying from Harlingen to Caribbean Islands

Discover the top 3 airlines that operate flights from Harlingen to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$306Average$645FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$309Average$500FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$378Average$544FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.