$239 Find Cheap Flights from Harlingen to Caribbean

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Harlingen to Caribbean departing on 1/19. 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$1,202
Oranjestad
Oranjestad2 stops$720
Nassau
Nassau2 stops$1,202

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 19 - Thu, Jan 22
United Airlines Logo
12:10 pm - 9:26 pm
HRL
-
SJU
7h 16m1 stop
United Airlines Logo
3:46 pm - 9:59 pm
SJU
-
HRL
8h 13m1 stop
$239United Airlines
Sat, Jan 24 - Tue, Jan 27
United Airlines Logo
9:20 am - 12:36 am
HRL
-
SJU
13h 16m2 stops
United Airlines Logo
2:05 am - 4:06 pm
SJU
-
HRL
16h 01m2 stops
$259United Airlines
Fri, Jan 23 - Fri, Jan 30
United Airlines Logo
7:00 am - 10:22 pm
HRL
-
SJU
13h 22m2 stops
United Airlines Logo
7:45 am - 4:06 pm
SJU
-
HRL
10h 21m1 stop
$279United Airlines
Fri, Jan 23 - Thu, Jan 29
United Airlines Logo
7:00 am - 10:22 pm
HRL
-
SJU
13h 22m2 stops
United Airlines Logo
2:05 am - 4:06 pm
SJU
-
HRL
16h 01m2 stops
$282United Airlines
Sun, Jan 25 - Wed, Jan 28
United Airlines Logo
12:10 pm - 9:26 pm
HRL
-
SJU
7h 16m1 stop
United Airlines Logo
8:10 am - 8:01 pm
SJU
-
HRL
13h 51m2 stops
$303United Airlines
Mon, Jan 19 - Wed, Jan 21
United Airlines Logo
7:00 am - 4:36 pm
HRL
-
SJU
7h 36m1 stop
United Airlines Logo
2:05 am - 4:06 pm
SJU
-
HRL
16h 01m2 stops
$323United Airlines
Tue, May 5 - Tue, May 5
United Airlines Logo
12:05 pm - 8:38 pm
HRL
-
SJU
7h 33m1 stop
United Airlines Logo
1:00 am - 4:03 pm
SJU
-
HRL
16h 03m2 stops
$324United Airlines
Mon, Jan 19 - Thu, Jan 22
American Airlines Logo
11:06 am - 10:26 pm
HRL
-
SJU
9h 20m1 stop
American Airlines Logo
3:54 pm - 11:21 pm
SJU
-
HRL
9h 27m1 stop
$357American Airlines
Wed, Jan 7 - Wed, Jan 14
American Airlines Logo
6:44 pm - 3:59 pm
HRL
-
SJU
19h 15m2 stops
American Airlines Logo
6:00 am - 2:46 pm
SJU
-
HRL
10h 46m2 stops
$362American Airlines
Sun, Feb 8 - Wed, Feb 11
Air Canada Logo
7:00 am - 12:55 pm
HRL
-
NAS
28h 55m2 stops
Air Canada Logo
1:50 pm - 7:58 pm
NAS
-
HRL
31h 08m2 stops
$1,202Air Canada
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$239
Most popular time to fly with an average 11% increase in price.
Flight from Harlingen to San Juan

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 4258 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

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.

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 pilot greased the landing and the crew was fantastic.

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports