$126 Find Cheap Flights from Harlingen to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Harlingen to Caribbean departing on 1/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Harlingen to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Oranjestad
Oranjestad2 stops$720
Nassau
Nassau2 stops$568
Oranjestad
Oranjestad2 stops$720
Nassau
Nassau2 stops$568

Book Cheap Harlingen to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Harlingen to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Harlingen to Caribbean

Mon, Jan 26 - Thu, Jan 29
American Airlines Logo
6:44 pm - 12:27 pmHRL-SJU
15h 43m2 stops
American Airlines Logo
7:07 am - 2:46 pmSJU-HRL
9h 39m1 stop
$301American Airlines
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Mon, Jan 26 - Thu, Jan 29
United Airlines Logo
9:20 am - 12:36 amHRL-SJU
13h 16m2 stops
United Airlines Logo
8:10 am - 8:01 pmSJU-HRL
13h 51m2 stops
$329United Airlines
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Mon, Jan 26 - Thu, Jan 29
United Airlines Logo
9:20 am - 12:36 amHRL-SJU
13h 16m2 stops
United Airlines Logo
8:10 am - 8:01 pmSJU-HRL
13h 51m2 stops
$369United Airlines
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Mon, Apr 20 - Fri, Apr 24
American Airlines Logo
7:54 pm - 2:35 pmHRL-SJU
17h 41m2 stops
American Airlines Logo
3:20 pm - 11:59 pmSJU-HRL
9h 39m1 stop
$391American Airlines
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Fri, May 8 - Sun, May 10
American Airlines Logo
7:54 pm - 2:35 pmHRL-SJU
17h 41m2 stops
American Airlines Logo
3:20 pm - 11:59 pmSJU-HRL
9h 39m1 stop
$450American Airlines
Find Deal
Fri, Jan 2 - Fri, Jan 16
American Airlines Logo
8:11 pm - 3:48 pmHRL-SJU
17h 37m2 stops
American Airlines Logo
6:00 am - 11:21 pmSJU-HRL
19h 21m2 stops
$479American Airlines
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Fri, May 8 - Sun, May 10
American Airlines Logo
7:54 pm - 2:35 pmHRL-SJU
17h 41m2 stops
American Airlines Logo
6:25 am - 11:59 pmSJU-HRL
18h 34m2 stops
$491American Airlines
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Mon, Apr 20 - Fri, Apr 24
American Airlines Logo
4:14 pm - 4:00 amHRL-SJU
10h 46m1 stop
American Airlines Logo
6:59 am - 4:09 pmSJU-HRL
10h 10m1 stop
$507American Airlines
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Fri, Jan 2 - Fri, Jan 16
American Airlines Logo
8:11 pm - 5:34 amHRL-SJU
7h 23m1 stop
American Airlines Logo
6:00 am - 11:21 pmSJU-HRL
19h 21m2 stops
$552American Airlines
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Wed, Jan 21 - Thu, Jan 22
American Airlines Logo
6:02 am - 6:03 pmHRL-NAS
11h 01m2 stops
American Airlines Logo
6:45 pm - 10:36 amNAS-HRL
16h 51m2 stops
$568American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Harlingen to Caribbean flights

Get data-powered insights and trends into flights from Harlingen to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Harlingen to Caribbean?

The average price of all round-trip flights from Harlingen to Caribbean clicked on KAYAK for each day over the last 12 months.

When flying from Harlingen to Caribbean, you should consider leaving on a Wednesday and avoid Fridays if you are looking for the best rates. For your return to Harlingen, you’ll find the best rates on Wednesdays and the most expensive ones on Saturdays.

Good to know

Cheapest flight$126
Most popular time to fly with an average 7% increase in price.
Flight from Harlingen to San Juan Airport

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Harlingen to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Harlingen to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Harlingen to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Harlingen to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Harlingen to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Harlingen to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Harlingen to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Harlingen to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $537 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $626.

Reviews of the top 3 airlines serving from Harlingen to Caribbean

 
Need help choosing which airline to fly with from Harlingen to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4253 reviews
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Seats had less pitch than a regional jet. Food was OK. Have to buy alcohol on US based carriers flying international. Boarding was a mess. Did not have bags but overhead space was gone quick. Would like to see the airlines enforce the one bag over and one bag under policy

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Crew was excellent. This was a relatively long flight though and had very little leg room, and no entertainment.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

Plane was crowded and even when we hit altitude, the plane was hot, not enough air flow.

Flight was delayed and missed my connection Lufthansa didn’t respond.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

A little bit more leg room in premium economy. I am 6’4”.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

I have a gluten allergy so did have any food

We were very rushed by a staff member at the gate when transferring from American Airlines to Fijian. Then the plane stayed put for ages anyhow! The plane was delayed and my bag sent to San Francisco instead of Fiji

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

The only thing to like was that we eventually got to our destination

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

We were delayed for a “couple of maintenance issues.” They were resolved rather quickly but a computer glitch caused someone in the airport to have to bring a physical copy of the paperwork so we could leave. I don’t know where they had to drive from to get to our plane but it took forever & we were 1 1/2 hrs late in leaving. The flight itself was fine.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports