HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$236+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Harlingen to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Harlingen to Caribbean

Keep the following information in mind while searching for Harlingen to Caribbean flight deals. Data was last updated September 15, 2025.

Round-trip from

$455
(United Airlines)

One-way from

$236
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$483
From Harlingen Valley Intl to Caribbean
Search Deals
One-way flight from Harlingen Valley Intl to Caribbean
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find 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 September 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:00 amHRL - SJU
1 stop9h 42mUnited Airlines
Fri 10/171:05 amSJU - HRL
2 stops13h 14mUnited Airlines
Deal found 9/14$455
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Mon 10/65:00 amHRL - SJU
1 stop9h 42mUnited Airlines
Thu 10/91:05 amSJU - HRL
2 stops13h 14mUnited Airlines
Deal found 9/13$465
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:00 amHRL - SJU
1 stop14h 38mUnited Airlines
Fri 10/171:05 amSJU - HRL
2 stops13h 14mUnited Airlines
Deal found 9/14$519
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 10/36:35 pmHRL - SJU
1 stop18h 40mAmerican Airlines
Mon 10/67:00 pmSJU - HRL
2 stops15h 38mAmerican Airlines
Deal found 9/13$543
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Mon 10/66:20 pmHRL - SJU
2 stops17h 24mAmerican Airlines
Fri 10/107:00 pmSJU - HRL
2 stops15h 38mAmerican Airlines
Deal found 9/13$553
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/122:05 pmHRL - SJU
3 stops26h 25mUnited Airlines
Fri 10/171:05 amSJU - HRL
2 stops13h 14mUnited Airlines
Deal found 9/14$556
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:00 amHRL - SJU
1 stop9h 42mUnited Airlines
Wed 10/157:00 amSJU - HRL
1 stop13h 41mUnited Airlines
Deal found 9/14$561
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:00 amHRL - AUA
1 stop7h 50mUnited Airlines
Wed 12/243:25 pmAUA - HRL
1 stop8h 34mUnited Airlines
Deal found 9/14$842
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/198:11 pmHRL - AUA
2 stops18h 39mAmerican Airlines
Wed 12/245:50 pmAUA - HRL
2 stops22h 28mAmerican Airlines
Deal found 9/14$1,068

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 September 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 10/6

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Thu 10/9

1:05 am-1:19 pm

2 stops13h 14m

$465

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Wed 10/15

5:00 am-8:38 pm

1 stop14h 38m

San Juan Luis Munoz Marin Intl

Fri 10/17

1:05 am-1:19 pm

2 stops13h 14m

$519

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Mon 10/6

6:20 pm-12:44 pm

2 stops17h 24m

San Juan Luis Munoz Marin Intl

Fri 10/10

7:00 pm-9:38 am

2 stops15h 38m

$553

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Tue 10/14

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Tue 10/14

1:05 am-4:13 pm

2 stops16h 08m

$565

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Fri 10/3

5:45 am-11:37 pm

2 stops16h 52m

San Juan Luis Munoz Marin Intl

Mon 10/6

7:00 pm-9:38 am

2 stops15h 38m

$594

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Tue 10/14

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Thu 10/16

1:05 am-11:18 pm

2 stops23h 13m

$605

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Tue 10/14

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Wed 10/15

1:05 am-11:18 pm

2 stops23h 13m

$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

4:15 pm-12:04 am

1 stop8h 49m

$635

HarlingenSan Juan

HRL - SJU

HRLSJU

Harlingen Valley Intl

Wed 9/17

2:51 pm-11:11 am

2 stops19h 20m

San Juan Luis Munoz Marin Intl

Fri 9/19

6:10 am-6:05 pm

2 stops12h 55m

$665

HarlingenOranjestad

HRL - AUA

HRLAUA

Harlingen Valley Intl

Fri 12/19

7:00 am-4:50 pm

1 stop7h 50m

Oranjestad Reina Beatrix

Wed 12/24

3:25 pm-9:59 pm

1 stop8h 34m

$842

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 18 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, September is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean (average of $254). Flying from Harlingen, Texas to Caribbean 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 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 September 15, 2025.

When flying from Harlingen, Texas to Caribbean, 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

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 September 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
8.0
Very good
4,245 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 9h 42m. 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 - Havana Jose Marti Intl or Harlingen Valley Intl - Nassau 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, September is the cheapest month in which you can book a flight from Harlingen, Texas to Caribbean (average of $254). Flying from Harlingen, Texas to Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Harlingen to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to Las Vegas flights
Dallas/Fort Worth to John F Kennedy Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to Los Angeles flights
Dallas/Fort Worth to Denver flights
Dallas/Fort Worth to Newark flights
Dallas/Fort Worth to Seattle flights
Hobby to John F Kennedy Intl flights
George Bush Intcntl to Cancún flights
Dallas/Fort Worth to Cancún flights
Hobby to LaGuardia flights
Dallas/Fort Worth to Boston flights
Dallas/Fort Worth to Dulles Intl flights
Hobby to Newark flights
Hobby to Las Vegas flights
Dallas/Fort Worth to Orlando flights
Dallas/Fort Worth to San Francisco flights
Dallas/Fort Worth to Midway flights
George Bush Intcntl to John F Kennedy Intl flights
Dallas/Fort Worth to Miami flights
George Bush Intcntl to Las Vegas flights
Dallas/Fort Worth to Baltimore flights
Dallas/Fort Worth to Mexico City flights
Hobby to Denver flights
Dallas/Fort Worth to Sky Harbor Intl flights
George Bush Intcntl to Newark flights
Austin to John F Kennedy Intl flights
Love Field to Las Vegas flights
Austin to Las Vegas flights
Dallas/Fort Worth to Reagan-National flights
Hobby to Cancún flights
Dallas/Fort Worth to Fort Lauderdale flights
Dallas/Fort Worth to Detroit flights
Hobby to Mexico City flights
George Bush Intcntl to LaGuardia flights
Dallas/Fort Worth to Narita flights
Austin to Newark flights
George Bush Intcntl to Denver flights
Dallas/Fort Worth to Salt Lake City flights
Hobby to Los Angeles flights
Dallas/Fort Worth to Haneda flights
George Bush Intcntl to Mexico City flights
Dallas/Fort Worth to Atlanta flights
Hobby to O'Hare Intl flights
Dallas/Fort Worth to Cozumel flights
Dallas/Fort Worth to San Diego flights
Dallas/Fort Worth to Heathrow flights
Dallas/Fort Worth to Hobby flights
Dallas/Fort Worth to Santa Ana flights

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$294Average$534FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$423Average$622FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$513Average$589FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.