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Caribbean Islands

$219+ Cheap flights from Harlingen (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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — SJU
Jul 23 — Jul 301
Wed 7/23
Wed 7/30
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 July 18, 2025.

Round-trip from

$219
(American Airlines)

Popular in

June

Cheapest in

January

Average price

$645
From Harlingen Valley Intl to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 18, 2025.

This American Airlines deal was found by Cheapflights users on 7/17. 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 9/136:35 pmHRL - SJU
2 stops19h 18mAmerican Airlines
Thu 9/181:37 pmSJU - HRL
2 stops21h 04mAmerican Airlines
Deal found 7/17$219
This United Airlines deal was found by Cheapflights users on 7/17. 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 10/35:00 amHRL - SJU
1 stop9h 42mUnited Airlines
Sat 10/112:55 pmSJU - HRL
1 stop7h 21mUnited Airlines
Deal found 7/17$405
This American Airlines deal was found by Cheapflights users on 7/17. 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 8/156:30 pmHRL - NAS
2 stops14h 22mAmerican Airlines
Fri 8/226:45 pmNAS - HRL
2 stops15h 47mAmerican Airlines
Deal found 7/17$544
This United Airlines deal was found by Cheapflights users on 7/17. 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 9/65:00 amHRL - STI
2 stops19h 46mUnited Airlines
Sat 9/136:00 amSTI - HRL
2 stops16h 52mUnited Airlines
Deal found 7/17$585
This United Airlines deal was found by Cheapflights users on 7/16. 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 8/51:59 pmHRL - NAS
1 stop24h 59mUnited Airlines
Tue 8/122:53 pmNAS - HRL
1 stop7h 57mUnited Airlines
Deal found 7/16$737
This Sun Country Air deal was found by Cheapflights users on 7/15. 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.
Sun 12/2111:37 amHRL - SJU
1 stop26h 24mSun Country Air
Fri 12/265:14 pmSJU - HRL
1 stop17h 38mSun Country Air
Deal found 7/15$816
This Southwest deal was found by Cheapflights users on 7/17. 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.
Thu 7/312:15 pmHRL - SJU
2 stops9h 40mSouthwest
Sun 8/32:00 pmSJU - HRL
2 stops10h 55mSouthwest
Deal found 7/17$895
This American Airlines deal was found by Cheapflights users on 7/16. 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 7/297:59 pmHRL - AUA
2 stops19h 11mAmerican Airlines
Sun 8/35:00 pmAUA - HRL
2 stops23h 57mAmerican Airlines
Deal found 7/16$920
This United deal was found by Cheapflights users on 7/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/317:10 amHRL - SJU
2 stops29h 40mMultiple Airlines
Sat 8/22:05 amSJU - HRL
1 stop12h 15mMultiple Airlines
Deal found 7/17$1,113
This United Airlines deal was found by Cheapflights users on 7/17. 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 7/295:10 amHRL - AUA
1 stop9h 10mUnited Airlines
Sun 8/34:30 pmAUA - HRL
2 stops24h 30mUnited Airlines
Deal found 7/17$1,135

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 July 18, 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

Sat 9/13

6:35 pm-2:53 pm

2 stops19h 18m

San Juan Luis Munoz Marin Intl

Thu 9/18

1:37 pm-9:41 am

2 stops21h 04m

$219

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Fri 10/3

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Sat 10/11

2:55 pm-9:16 pm

1 stop7h 21m

$405

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

Fri 8/15

6:30 pm-9:52 am

2 stops14h 22m

Nassau Intl

Fri 8/22

6:45 pm-9:32 am

2 stops15h 47m

$544

HarlingenSantiago de los Caballeros

HRL - STI

HRLSTI

Harlingen Valley Intl

Sat 9/6

5:00 am-1:46 am

2 stops19h 46m

Santiago de los Caballeros

Sat 9/13

6:00 am-9:52 pm

2 stops16h 52m

$585

HarlingenNassau

HRL - NAS

HRLNAS

Harlingen Valley Intl

Tue 8/5

1:59 pm-3:58 pm

1 stop24h 59m

Nassau Intl

Tue 8/12

2:53 pm-9:50 pm

1 stop7h 57m

$737

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Sun 12/21

11:37 am-4:01 pm

1 stop26h 24m

San Juan Luis Munoz Marin Intl

Fri 12/26

5:14 pm-8:52 am

1 stop17h 38m

$816

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Thu 7/31

2:15 pm-12:55 am

2 stops9h 40m

San Juan Luis Munoz Marin Intl

Sun 8/3

2:00 pm-11:55 pm

2 stops10h 55m

$895

HarlingenOranjestad

HRL - AUA

HRLAUA

Harlingen Valley Intl

Tue 7/29

7:59 pm-4:10 pm

2 stops19h 11m

Oranjestad Reina Beatrix

Sun 8/3

5:00 pm-3:57 pm

2 stops23h 57m

$920

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Thu 7/31

7:10 am-1:50 pm

2 stops29h 40m

San Juan Luis Munoz Marin Intl

Sat 8/2

2:05 am-1:20 pm

1 stop12h 15m

$1,113

HarlingenOranjestad

HRL - AUA

HRLAUA

Harlingen Valley Intl

Tue 7/29

5:10 am-3:20 pm

1 stop9h 10m

Oranjestad Reina Beatrix

Sun 8/3

4:30 pm-4:00 pm

2 stops24h 30m

$1,135

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/16

Showing 1-10 of 12 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 to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Harlingen to Caribbean Islands (average of $254). Flying from Harlingen 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 July 18, 2025.

When flying from Harlingen 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.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated July 18, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Harlingen to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,864 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Sun Country Air
6.9
Okay
334 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

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

    While some choose either Harlingen Valley Intl - Oranjestad Reina Beatrix or Harlingen Valley Intl - Nassau Intl, Harlingen Valley Intl - San Juan Luis Munoz Marin Intl is the most popular route from Harlingen 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 to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Harlingen to Caribbean Islands (average of $254). Flying from Harlingen 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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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 July 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$544FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$423Average$624FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$511Average$589FlexibilityNo cancel feeOn-time63%

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