$266 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 5/31. 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

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

Tue, May 5 - Wed, May 6
United Airlines Logo
12:10 pm - 8:38 pm
HRL
-
SJU
7h 28m
1 stop
United Airlines Logo
7:00 am - 4:04 pm
SJU
-
HRL
10h 04m
1 stop
$345United Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
7:00 am - 11:50 pm
HRL
-
SJU
15h 50m
2 stops
United Airlines Logo
7:00 am - 4:04 pm
SJU
-
HRL
10h 04m
1 stop
$433United Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
7:00 am - 11:50 pm
HRL
-
SJU
15h 50m
2 stops
United Airlines Logo
7:00 am - 4:04 pm
SJU
-
HRL
10h 04m
1 stop
$469United Airlines
Fri, Jan 30 - Mon, Feb 2
American Airlines Logo
3:22 pm - 10:48 am
HRL
-
SJU
17h 26m
2 stops
American Airlines Logo
5:51 pm - 10:36 am
SJU
-
HRL
18h 45m
2 stops
$506American Airlines
Fri, Jan 30 - Mon, Feb 2
American Airlines Logo
11:06 am - 11:59 pm
HRL
-
SJU
10h 53m
2 stops
American Airlines Logo
7:07 am - 11:21 pm
SJU
-
HRL
18h 14m
1 stop
$535American Airlines
Fri, Jan 30 - Mon, Feb 2
United Airlines Logo
12:10 pm - 9:26 pm
HRL
-
SJU
7h 16m
1 stop
United Airlines Logo
3:46 pm - 9:59 pm
SJU
-
HRL
8h 13m
1 stop
$549United Airlines
Mon, Jun 8 - Sun, Jun 14
American Airlines Logo
4:56 pm - 9:33 am
HRL
-
SJU
15h 37m
2 stops
American Airlines Logo
12:39 am - 10:15 am
SJU
-
HRL
10h 36m
1 stop
$551American Airlines
Wed, May 27 - Sat, May 30
American Airlines Logo
4:56 pm - 9:33 am
HRL
-
SJU
15h 37m
2 stops
American Airlines Logo
12:39 am - 10:15 am
SJU
-
HRL
10h 36m
1 stop
$591American Airlines
Wed, May 27 - Sat, May 30
American Airlines Logo
4:56 pm - 4:32 am
HRL
-
SJU
10h 36m
1 stop
American Airlines Logo
12:39 am - 10:15 am
SJU
-
HRL
10h 36m
1 stop
$636American Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
12:10 pm - 12:34 pm
HRL
-
SJU
23h 24m
2 stops
United Airlines Logo
4:55 pm - 11:23 am
SJU
-
HRL
19h 28m
2 stops
$640United Airlines
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.

Which airlines provide the cheapest flights from Harlingen to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Harlingen to Caribbean were found on United Airlines ($345) and American Airlines ($722).

Good to know

Low seasonFebruary
Cheapest flight$266
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 26% lower on average.
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.

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 4261 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

The seats were comfortable, and the boarding process was pretty smooth.

10.0 ExcellentJohn, Jan 2026
BWI - MDW
Read more Southwest reviews

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Delayed, toilets did not flush, pilot parked to far away from Gate

I like flying first class, and United has a nice one

Unbelievably poor service from flight attendants. They didn’t even do water service on a four hour flight. Just disrespectful.

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 seat cushions were very worn so they were extremely uncomfortable.

Delayed, no updates, had a rewards number but was not working

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The professionals have excellent customer service, the seats don´t have enough space.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

Seats were much more cramped then on the 737. Narrower and rows closer together. Flight was absolutely packed and the plugs under the seats didn't work. Was forced to check my bag even though previous flight had no issue with it.

Good food & refreshment. The seats and entrainment screens are modern compared to others. The staff though pleasant serve and attend to passengers based on nationality. Some get served first others last regardless of their seating positions.

The economy seats are very cramped and the food was bizarre. However, I did like the greek yogurt option for breakfast.

We never made it due to delays on both ends. Gate attendant said it was mechanical but the system said otherwise, so no compensation. That’s not right.

The pilot greased the landing and the crew was fantastic.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports