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Caribbean Islands

$270+ 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 3/30. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — SJU
mar. 15 — mar. 221
dom. 3/15
dom. 3/22
1 adult, Economy
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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 febrero 13, 2026.

This American Airlines deal was found by Cheapflights users on 2/13. 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.
lun. 3/308:06 pm
HRL
-
SJU
2 stops17h 44m
American Airlines
mié. 4/83:44 pm
SJU
-
HRL
2 stops19h 33m
American Airlines
Deal found 2/13$270
This United Airlines deal was found by Cheapflights users on 2/12. 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.
mar. 5/512:10 pm
HRL
-
SJU
1 stop7h 28m
United Airlines
mié. 5/67:20 am
SJU
-
HRL
2 stops13h 40m
United Airlines
Deal found 2/12$395
This United Airlines deal was found by Cheapflights users on 2/10. 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.
vie. 3/277:00 am
HRL
-
NAS
1 stop5h 33m
United Airlines
mar. 4/72:53 pm
NAS
-
HRL
1 stop8h 06m
United Airlines
Deal found 2/10$436
This American Airlines deal was found by Cheapflights users on 2/13. 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.
lun. 3/238:06 pm
HRL
-
SJU
2 stops17h 44m
American Airlines
jue. 3/266:33 am
SJU
-
HRL
1 stop14h 03m
American Airlines
Deal found 2/13$450
This American Airlines deal was found by Cheapflights users on 2/13. 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.
mar. 7/288:05 pm
HRL
-
SJU
1 stop7h 27m
American Airlines
mar. 8/117:05 pm
SJU
-
HRL
2 stops15h 27m
American Airlines
Deal found 2/13$462
This American Airlines deal was found by Cheapflights users on 2/10. 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.
mié. 5/66:00 am
HRL
-
SJU
2 stops11h 10m
American Airlines
dom. 5/1011:59 pm
SJU
-
HRL
1 stop11h 18m
American Airlines
Deal found 2/10$471
This United Airlines deal was found by Cheapflights users on 2/10. 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.
lun. 3/307:00 am
HRL
-
SJU
1 stop7h 42m
United Airlines
vie. 4/32:55 pm
SJU
-
HRL
1 stop8h 04m
United Airlines
Deal found 2/10$481
This Southwest deal was found by Cheapflights users on 2/13. 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.
lun. 3/236:50 am
HRL
-
SJU
2 stops8h 40m
Southwest
jue. 3/261:05 pm
SJU
-
HRL
2 stops12h 00m
Southwest
Deal found 2/13$493
This Southwest deal was found by Cheapflights users on 2/10. 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.
mié. 5/66:20 am
HRL
-
SJU
2 stops10h 50m
Southwest
dom. 5/1011:40 am
SJU
-
HRL
2 stops12h 20m
Southwest
Deal found 2/10$505
This American Airlines deal was found by Cheapflights users on 2/10. 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.
vie. 3/272:45 pm
HRL
-
NAS
1 stop24h 38m
American Airlines
mar. 4/75:28 pm
NAS
-
HRL
2 stops17h 49m
American Airlines
Deal found 2/10$585
This Southwest deal was found by Cheapflights users on 2/10. 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.
vie. 3/276:50 am
HRL
-
NAS
2 stops10h 40m
Southwest
mar. 4/78:45 am
NAS
-
HRL
2 stops13h 10m
Southwest
Deal found 2/10$588
This United Airlines deal was found by Cheapflights users on 2/9. 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.
mar. 10/275:15 am
HRL
-
STI
2 stops16h 36m
United Airlines
vie. 10/303:00 pm
STI
-
HRL
2 stops31h 44m
United Airlines
Deal found 2/9$724

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 febrero 13, 2026.

Round-trip from

$270
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$347
From Harlingen Valley Intl to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($232 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($81 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 febrero 13, 2026.
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

sáb. 5/9

8:03 pm-2:42 pm

1 stop17h 39m

San Juan Luis Munoz Marin Intl

vie. 5/15

5:45 am-10:51 pm

2 stops18h 06m

$270

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

lun. 3/30

8:06 pm-2:11 pm

1 stop17h 05m

San Juan Luis Munoz Marin Intl

mié. 4/8

3:44 pm-10:17 am

2 stops19h 33m

$370

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

mar. 5/5

12:10 pm-8:38 pm

1 stop7h 28m

San Juan Luis Munoz Marin Intl

mié. 5/6

7:00 am-4:04 pm

1 stop10h 04m

$395

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

vie. 3/27

7:00 am-1:33 pm

1 stop5h 33m

Nassau Intl

mar. 4/7

2:53 pm-9:59 pm

1 stop8h 06m

$436

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

dom. 8/2

4:56 pm-1:51 pm

2 stops19h 55m

San Juan Luis Munoz Marin Intl

mar. 8/11

7:05 pm-9:32 am

2 stops15h 27m

$462

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

vie. 3/27

6:50 am-6:30 pm

2 stops10h 40m

Nassau Intl

mar. 4/7

8:45 am-8:55 pm

2 stops13h 10m

$588

HarlingenOranjestad

HRL - AUA

HRLAUA

Harlingen Valley Intl

vie. 3/13

9:20 am-4:10 pm

1 stop29h 50m

Oranjestad Reina Beatrix

mar. 3/17

4:50 pm-11:16 am

2 stops19h 26m

$961

HarlingenOranjestad

HRL - AUA

HRLAUA

Harlingen Valley Intl

vie. 3/13

8:06 pm-4:10 pm

2 stops19h 04m

Oranjestad Reina Beatrix

mar. 3/17

2:39 pm-10:12 am

2 stops20h 33m

$1,001

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

dom. 3/15

9:20 am-5:11 am

1 stop18h 51m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

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, February is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean Islands (average of $240). Flying from Harlingen, Texas to Caribbean Islands in October is currently the most expensive (average of $449). 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 28m. Fly via American Airlines, United Airlines, or Southwest 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 - Gregory Town North Eleuthera or Harlingen Valley Intl - Havana Jose Marti 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, February is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean Islands (average of $240). Flying from Harlingen, Texas to Caribbean Islands in October is currently the most expensive (average of $449). 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 febrero 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$260Average$500FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$306Average$645FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$378Average$544FlexibilityNo cancel feeOn-time63%

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