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Caribbean Islands

$236+ Cheap flights from Harlingen, TX (HRL) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — SJU
Oct 23 — Oct 301
Thu 10/23
Thu 10/30
1 adult, Economy
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Cheap 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 September 23, 2025.

Round-trip from

$590
(American Airlines)

One-way from

$236
(American Airlines)

Popular in

October

Cheapest in

January

Average price

$483
From Harlingen Valley Intl to Caribbean Islands
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One-way flight from Harlingen Valley Intl to Caribbean Islands
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Highest demand for flights based on searches. 11% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 23, 2025.

This United Airlines deal was found by Cheapflights users on 9/22. 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.
Thu 10/27:00 amHRL - SJU
2 stops15h 57mUnited Airlines
Tue 10/71:05 amSJU - HRL
2 stops13h 14mUnited Airlines
Deal found 9/22$502
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Thu 10/25:45 amHRL - SJU
2 stops16h 52mAmerican Airlines
Wed 10/87:00 amSJU - HRL
2 stops17h 04mAmerican Airlines
Deal found 9/22$530
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Mon 11/246:38 pmHRL - SJU
2 stops13h 32mAmerican Airlines
Wed 11/266:42 pmSJU - HRL
2 stops17h 01mAmerican Airlines
Deal found 9/22$590
This Mytrip deal was found by Cheapflights users on 9/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/211:47 amHRL - SJU
3 stops22h 17mMultiple Airlines
Tue 10/72:49 amSJU - HRL
3 stops32h 53mMultiple Airlines
Deal found 9/22$619
This United Airlines deal was found by Cheapflights users on 9/21. 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 9/285:00 amHRL - SJU
1 stop9h 42mUnited Airlines
Sun 10/52:55 pmSJU - HRL
1 stop9h 23mUnited Airlines
Deal found 9/21$628
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Sun 9/282:38 pmHRL - SJU
2 stops19h 33mAmerican Airlines
Sun 10/53:05 pmSJU - HRL
1 stop8h 47mAmerican Airlines
Deal found 9/21$650
This Sun Country Air deal was found by Cheapflights users on 9/21. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/279:55 amHRL - SJU
1 stop26h 15mSun Country Air
Tue 12/305:14 pmSJU - HRL
1 stop19h 39mSun Country Air
Deal found 9/21$656
This Southwest deal was found by Cheapflights users on 9/20. 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.
Wed 9/247:25 amHRL - SJU
2 stops14h 20mSouthwest
Fri 9/268:15 amSJU - HRL
2 stops10h 50mSouthwest
Deal found 9/20$665
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 9/262:51 pmHRL - SJU
2 stops19h 20mAmerican Airlines
Sun 9/286:10 amSJU - HRL
2 stops17h 42mAmerican Airlines
Deal found 9/22$695
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Sat 11/298:02 pmHRL - SJU
1 stop16h 58mAmerican Airlines
Sun 12/76:42 pmSJU - HRL
2 stops16h 59mAmerican Airlines
Deal found 9/22$704

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 September 23, 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

Thu 10/2

7:00 am-11:57 pm

2 stops15h 57m

San Juan Luis Munoz Marin Intl

Tue 10/7

1:05 am-1:19 pm

2 stops13h 14m

$502

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Thu 10/2

5:45 am-11:37 pm

2 stops16h 52m

San Juan Luis Munoz Marin Intl

Wed 10/8

7:00 am-11:04 pm

2 stops17h 04m

$530

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Mon 11/24

6:38 pm-10:10 am

2 stops13h 32m

San Juan Luis Munoz Marin Intl

Wed 11/26

7:15 am-3:36 pm

1 stop10h 21m

$590

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Thu 10/2

11:47 am-11:04 am

3 stops22h 17m

San Juan Luis Munoz Marin Intl

Tue 10/7

2:49 am-10:42 am

3 stops32h 53m

$619

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Sun 9/28

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Sun 10/5

2:55 pm-11:18 pm

1 stop9h 23m

$628

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

Tue 3/10

5:50 am-2:29 pm

1 stop7h 39m

Nassau Intl

Wed 3/11

2:35 pm-9:45 am

2 stops20h 10m

$639

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Sun 9/28

2:38 pm-11:11 am

2 stops19h 33m

San Juan Luis Munoz Marin Intl

Sun 10/5

7:05 pm-2:19 pm

2 stops20h 14m

$650

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Fri 9/26

7:00 am-11:57 pm

2 stops15h 57m

San Juan Luis Munoz Marin Intl

Sun 9/28

2:55 pm-11:18 pm

1 stop9h 23m

$665

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Fri 9/26

6:35 pm-2:15 pm

1 stop18h 40m

San Juan Luis Munoz Marin Intl

Sun 9/28

6:10 am-10:52 pm

2 stops17h 42m

$695

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Thu 1/8

12:07 pm-10:14 pm

1 stop8h 07m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/22

Showing 1-10 of 15 results
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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, September is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean Islands (average of $254). Flying from Harlingen, Texas to Caribbean Islands in June is currently the most expensive (average of $339). 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.

What is the cheapest time of day to fly from HRL to EPX?

Find hourly flight availability from Harlingen to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 23, 2025.

When flying from Harlingen, Texas to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 15h 57m. Fly via United Airlines or American Airlines to get the fastest option. Airlines will cover a distance of 2086 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 - Havana Jose Marti Intl or Harlingen Valley Intl - Nassau Intl, 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, September is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean Islands (average of $254). Flying from Harlingen, Texas to Caribbean Islands in June is currently the most expensive (average of $339). 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

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Alternative routes for Harlingen to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$294Average$534FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$423Average$631FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$513Average$589FlexibilityNo cancel feeOn-time63%

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