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$130+ Cheap flights from Harlingen, TX (HRL) to Caribbean

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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — SJU
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap flight deals from Harlingen to Caribbean

Cheapest flights from Harlingen to Caribbean
Explore the most affordable flight options available from Harlingen to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 5/912:10 pm
HRL
-
SJU
1 stop7h 28m
United Airlines
Tue 5/127:20 am
SJU
-
HRL
2 stops13h 40m
United Airlines
Deal found 1/27$260
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 6/97:15 am
HRL
-
SJU
1 stop7h 27m
United Airlines
Fri 6/121:00 am
SJU
-
HRL
2 stops13h 14m
United Airlines
Deal found 1/27$344
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/32:47 pm
HRL
-
SJU
1 stop12h 45m
American Airlines
Wed 5/63:44 pm
SJU
-
HRL
2 stops19h 33m
American Airlines
Deal found 1/27$363
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/12:47 pm
HRL
-
SJU
1 stop12h 45m
American Airlines
Tue 5/53:44 pm
SJU
-
HRL
2 stops19h 33m
American Airlines
Deal found 1/27$403
This Southwest deal was found by Cheapflights users on 1/27. 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 5/32:35 pm
HRL
-
SJU
2 stops8h 10m
Southwest
Wed 5/65:35 am
SJU
-
HRL
2 stops11h 25m
Southwest
Deal found 1/27$413
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 5/17:00 am
HRL
-
SJU
1 stop7h 42m
United Airlines
Tue 5/52:55 pm
SJU
-
HRL
1 stop8h 04m
United Airlines
Deal found 1/27$433
This Southwest deal was found by Cheapflights users on 1/27. 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.
Fri 5/112:30 pm
HRL
-
SJU
2 stops10h 25m
Southwest
Tue 5/52:00 pm
SJU
-
HRL
2 stops9h 00m
Southwest
Deal found 1/27$455
This American Airlines deal was found by Cheapflights users on 1/27. 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 8/34:56 pm
HRL
-
SJU
1 stop10h 36m
American Airlines
Mon 8/107:05 pm
SJU
-
HRL
2 stops15h 27m
American Airlines
Deal found 1/27$466
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Tue 5/57:00 am
HRL
-
SJU
1 stop7h 42m
United Airlines
Thu 5/77:00 am
SJU
-
HRL
1 stop10h 04m
United Airlines
Deal found 1/26$474
This American Airlines deal was found by Cheapflights users on 1/27. 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 8/1410:02 am
HRL
-
STI
2 stops25h 29m
American Airlines
Mon 8/241:31 pm
STI
-
HRL
2 stops21h 01m
American Airlines
Deal found 1/27$563
This American Airlines deal was found by Cheapflights users on 1/27. 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 10/226:20 pm
HRL
-
STI
2 stops16h 50m
American Airlines
Mon 11/24:36 pm
STI
-
HRL
2 stops21h 02m
American Airlines
Deal found 1/27$603
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/3010:47 am
HRL
-
STI
2 stops24h 36m
American Airlines
Mon 5/111:32 pm
STI
-
HRL
2 stops21h 45m
American Airlines
Deal found 1/27$653

Find flight deals from Harlingen to Caribbean

Keep the following information in mind while searching for Harlingen to Caribbean flight deals. Data was last updated January 28, 2026.

Round-trip from

$260
(United Airlines)

One-way from

$130
(United Airlines)

Popular in

December

Cheapest in

February

Average price

$400
From Harlingen Valley Intl to Caribbean
Search Deals
One-way flight from Harlingen Valley Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($199 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($83 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Harlingen to Caribbean 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 January 28, 2026.
Use the filters below to find and compare flights from Harlingen to Caribbean that are best for you.

Fly from

Harlingen

Fly to

Caribbean

Route

Depart

Return

Price

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Sat 5/9

12:10 pm-8:38 pm

1 stop7h 28m

San Juan Luis Munoz Marin Intl

Tue 5/12

7:00 am-4:04 pm

1 stop10h 04m

$260

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Tue 6/9

7:15 am-3:42 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Fri 6/12

1:00 am-1:14 pm

2 stops13h 14m

$344

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Sun 5/3

2:47 pm-4:32 am

1 stop12h 45m

San Juan Luis Munoz Marin Intl

Wed 5/6

3:44 pm-10:17 am

2 stops19h 33m

$363

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Sun 5/3

2:35 pm-11:45 pm

2 stops8h 10m

San Juan Luis Munoz Marin Intl

Wed 5/6

5:35 am-4:00 pm

2 stops11h 25m

$413

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Fri 5/1

7:00 am-3:42 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Tue 5/5

2:55 pm-9:59 pm

1 stop8h 04m

$433

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Fri 5/1

12:30 pm-11:55 pm

2 stops10h 25m

San Juan Luis Munoz Marin Intl

Tue 5/5

2:00 pm-10:00 pm

2 stops9h 00m

$455

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Tue 5/5

12:10 pm-8:38 pm

1 stop7h 28m

San Juan Luis Munoz Marin Intl

Thu 5/7

2:55 pm-9:59 pm

1 stop8h 04m

$474

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

Sun 2/15

12:10 pm-8:10 pm

2 stops31h 00m

Nassau Intl

Thu 2/19

9:10 pm-7:58 pm

2 stops23h 48m

$1,306

HarlingenSantiago de los Caballeros

HRL - STI

HRLSTI

Harlingen Valley Intl

Thu 4/30

2:47 pm-12:23 pm

3 stops20h 36m

Santiago de los Caballeros

Mon 5/11

1:32 pm-10:17 am

2 stops21h 45m

$2,453

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Mon 2/23

6:46 pm-10:00 am

2 stops13h 14m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 15 results
1
2

Best time to book a flight from Harlingen to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, February is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean (average of $240). Flying from Harlingen, Texas to Caribbean 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.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated January 28, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Harlingen to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,206 reviews
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,198 reviews
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Harlingen to Caribbean. 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?

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

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

    Departing from Harlingen, Texas to Caribbean will take you 7h 28m. There are 2086 mi between Harlingen, Texas and Caribbean. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The most popular route from Harlingen, Texas to Caribbean is Harlingen Valley Intl - San Juan Luis Munoz Marin Intl. You may also consider Harlingen Valley Intl - Oranjestad Reina Beatrix or Harlingen Valley Intl - Gregory Town North Eleuthera.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Harlingen to Caribbean 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?

    Currently, February is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean (average of $240). Flying from Harlingen, Texas to Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Harlingen to Caribbean

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

Discover the top 3 airlines that operate flights from Harlingen to Caribbean. 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$260Average$498FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$306Average$645FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$378Average$544FlexibilityNo cancel feeOn-time63%

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