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$278+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — SJU
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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 December 15, 2025.

This American Airlines deal was found by Cheapflights users on 12/14. 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 12/255:34 amHRL - SJU
1 stop15h 48mAmerican Airlines
Mon 1/125:51 pmSJU - HRL
2 stops18h 45mAmerican Airlines
Deal found 12/14$482
This Sun Country Air deal was found by Cheapflights users on 12/15. 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.
Tue 12/3010:55 amHRL - SJU
1 stop27h 18mSun Country Air
Sat 1/34:30 pmSJU - HRL
1 stop20h 29mSun Country Air
Deal found 12/15$847
This Sun Country Air deal was found by Cheapflights users on 12/14. 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.
Fri 12/2612:37 pmHRL - SJU
1 stop24h 48mSun Country Air
Thu 1/15:14 pmSJU - HRL
1 stop19h 39mSun Country Air
Deal found 12/14$994
This American Airlines deal was found by Cheapflights users on 12/14. 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 12/265:34 amHRL - SJU
1 stop15h 48mAmerican Airlines
Thu 1/15:18 amSJU - HRL
2 stops15h 58mAmerican Airlines
Deal found 12/14$995
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/305:20 pmHRL - SJU
2 stops25h 40mUnited Airlines
Sat 1/37:45 amSJU - HRL
1 stop10h 21mUnited Airlines
Deal found 12/15$1,125
This United Airlines deal was found by Cheapflights users on 12/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:00 amHRL - SJU
2 stops28h 17mUnited Airlines
Sat 12/203:46 pmSJU - HRL
1 stop8h 13mUnited Airlines
Deal found 12/13$1,999

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 December 15, 2025.

Round-trip from

$302
(American Airlines)

One-way from

$278
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$1,475
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. 20% potential increase in price ($165 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($84 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 15, 2025.
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

Mon 1/19

6:02 am-3:04 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Wed 1/28

1:24 pm-10:36 am

2 stops23h 12m

$302

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Sun 1/25

12:10 pm-9:26 pm

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:45 am-4:06 pm

1 stop10h 21m

$329

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Mon 1/19

12:10 pm-9:26 pm

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:46 pm-9:59 pm

1 stop8h 13m

$330

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Thu 2/19

2:43 pm-10:07 am

2 stops17h 24m

San Juan Luis Munoz Marin Intl

Tue 2/24

8:15 am-6:16 pm

2 stops12h 01m

$391

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Fri 1/9

3:22 pm-10:48 am

2 stops17h 26m

San Juan Luis Munoz Marin Intl

Sun 1/18

7:12 pm-10:36 am

2 stops17h 24m

$441

HarlingenSantiago de los Caballeros

HRL - STI

HRLSTI

Harlingen Valley Intl

Sun 1/18

7:00 am-11:51 pm

2 stops14h 51m

Santiago de los Caballeros

Thu 1/22

4:00 pm-11:26 am

2 stops21h 26m

$672

HarlingenOranjestad

HRL - AUA

HRLAUA

Harlingen Valley Intl

Mon 1/19

9:20 am-1:50 pm

2 stops26h 30m

Oranjestad Reina Beatrix

Thu 1/22

5:50 pm-4:06 pm

2 stops24h 16m

$720

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

Tue 2/3

9:20 am-12:25 pm

2 stops26h 05m

Nassau Intl

Thu 2/5

1:55 pm-4:06 pm

2 stops27h 11m

$1,122

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

Wed 1/28

6:02 am-5:55 pm

3 stops10h 53m

Nassau Intl

Wed 2/4

2:58 pm-11:21 pm

2 stops9h 23m

$2,239

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Thu 1/8

6:44 pm-1:41 pm

2 stops16h 57m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 16 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, January is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean (average of $244). Flying from Harlingen, Texas to Caribbean 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.

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

Find hourly flight availability from Harlingen to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 15, 2025.

One of the essential ways to save on airfare from Harlingen, Texas to Caribbean is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 42% on airfare.

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 December 15, 2025.
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
7.9
Good
4,250 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

7.9

Food

7.0

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

7.9

Food

7.0

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
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

7.9

Food

7.0

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
11,051 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

7.9

Food

7.0

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 02m. 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 - Gregory Town North Eleuthera or Harlingen Valley Intl - Havana Jose Marti Intl.

  • 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, January is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean (average of $244). Flying from Harlingen, Texas to Caribbean 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

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Alternative routes for Harlingen to Caribbean

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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$306Average$645FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$309Average$500FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$378Average$544FlexibilityNo cancel feeOn-time63%

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