$158 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 7/31. 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

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Best Caribbean Flight Deals from Harlingen

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Oranjestad
Oranjestad2 stops$695
Nassau
Nassau2 stops$544
Oranjestad
Oranjestad2 stops$695
Nassau
Nassau2 stops$544

Cheap Flights from Harlingen to Caribbean

 
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

Sat, Sep 13 - Thu, Sep 18
American Airlines Logo
6:35 pm - 2:15 pmHRL-SJU
18h 40m1 stop
American Airlines Logo
7:05 pm - 9:41 amSJU-HRL
15h 36m2 stops
$315American Airlines
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Sat, Sep 13 - Thu, Sep 18
American Airlines Logo
6:35 pm - 2:15 pmHRL-SJU
18h 40m1 stop
American Airlines Logo
7:05 pm - 9:41 amSJU-HRL
15h 36m2 stops
$355American Airlines
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Thu, Jul 24 - Thu, Aug 14
American Airlines Logo
4:27 pm - 5:06 amHRL-SJU
11h 39m1 stop
American Airlines Logo
5:15 pm - 9:32 amSJU-HRL
17h 17m2 stops
$400American Airlines
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Sat, Sep 13 - Wed, Sep 17
United Airlines Logo
5:20 pm - 2:44 pmHRL-SJU
20h 24m2 stops
United Airlines Logo
1:05 am - 9:52 pmSJU-HRL
21h 47m2 stops
$417United Airlines
Find Deal
Sat, Sep 13 - Thu, Sep 18
American Airlines Logo
6:35 pm - 2:15 pmHRL-SJU
18h 40m1 stop
American Airlines Logo
3:05 pm - 10:52 pmSJU-HRL
8h 47m1 stop
$440American Airlines
Find Deal
Tue, Jul 29 - Mon, Aug 4
Southwest Logo
9:45 am - 10:25 pmHRL-SJU
11h 40m1 stop
Southwest Logo
10:05 am - 8:00 pmSJU-HRL
10h 55m2 stops
$520Southwest
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Thu, Jul 24 - Thu, Aug 14
United Airlines Logo
5:20 pm - 5:30 amHRL-SJU
11h 10m1 stop
United Airlines Logo
7:00 am - 4:00 pmSJU-HRL
10h 00m1 stop
$546United Airlines
Find Deal
Thu, Jul 24 - Thu, Aug 14
Southwest Logo
5:15 am - 6:00 pmHRL-SJU
11h 45m2 stops
Southwest Logo
2:40 pm - 10:15 pmSJU-HRL
8h 35m2 stops
$625Southwest
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Tue, Jul 29 - Sun, Aug 3
 Logo
7:10 am - 11:30 amHRL-SJU
27h 20m2 stops
 Logo
1:05 am - 9:50 pmSJU-HRL
21h 45m2 stops
Fri, Nov 7 - Tue, Nov 11
 Logo
7:27 am - 10:00 amHRL-AUA
24h 33m2 stops
 Logo
11:10 am - 10:59 amAUA-HRL
25h 49m3 stops
$1,032
Find Deal
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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 Sundays and the most expensive ones on Saturdays.


Good to know

High seasonMarch
Cheapest flight$158
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 4266 reviews
8.0Comfort
7.0Food
8.6Crew
7.6Entertainment
8.2Boarding
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Although the flight was delayed the crew and the flight itself were very good. Couldn't fault anything and after the disappointment of being abandoned in the US by BA it was a welcome relief to travel with United

Gate agent did not hold flight for connection, provided no assistance to get new flight

Boarding experience was smooth. Flight attendants were friendly and helpful. Entertainment system on the Houston-Edmonton flight did not function for passengers on the left side of the aisle. On the bird's eye flight from Quito to Houston, they should not serve a meal. No one needs to eat after midnight and it is disturbing for those passengers trying to sleep.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

My suitcase was completed destroyed. The top part is broken and unusable now.

We boarded but then sat there waiting on some missed connection people to get on so we sat for about 15 minutes for that. Then we sat again because the passenger manifest was wrong and they had to figure it out before we could leave. That took about another 20 minutes or so. The crew was working hard to figure it out so it’s not their fault. It ended up being a system glitch where someone was upgraded to first class while another person was also in the same seat and it just created a mess that took a little while to figure out. They literally went to every person on the plane asking their names to see who was sitting in the wrong seat. I also hate the entertainment that must be watched on your phone or tablet. Just give us setback screens. It’s so much better. Almost every Delta flight has this now and it is so nice to have them. The crew did a great job. I have no complaints from them. They were very hard working, even with the mishap and a disgruntled passenger.

My priority checked bag was not loaded on the flight. I had to sit in baggage claim in Las Vegas for 2 1/2 hours waiting for the next flight. All baggage staff were very helpful, tracking showed it as scanned for loading. Nobody told me why it wasn't on my flight.

All male crew was just too woke for me. I felt like a sardine. I will never take a window seat or the rearmost seat again. I booked early and did not pay for seat selection and that was a mistake. The security at IAH was atrocious. I was violated and radiated as I was in a hurry to connect to my other flight. I may have lost items under the seat in front of me that I couldn't see nor bend over to look.

Food choices were very limited. Taste of the dishes was average.

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

The flight delay in Dallas created a domino effect that impacted all of the connecting flights. It also increased the number of connections. I missed my flight from Casablanca to Marrakech because of the tight turnaround when landing in Casablanca. . CMN airport was understaffed. Only one person could help while other employees were just watching him. It was an extremely frustrating situation. People were crying and slamming their palms on the counter when speaking to the customer service provider, Allabough (man’s name?). Allabough couldn’t change my flight in the system. simultaneously, I was on the call with America. Airlines customer service rep named Solomon that said he couldn’t change it either. So, I took a ONYA voyages train to from Casablanca to Marrakech to get there on Friday June 26. This was unpredictable trip.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

At the beginning of the flight there was some turbulence and the announcement was made that there would be no beverage service. The turbulence only last about 5 minutes then it was smooth sailing. I noticed that first class got their service, but the rest of us did not.

Update departure times in a more timely manner. We are not boarding on time if the plane isn’t arriving until after our scheduled departure time.

Update.us on flight information in a more timely manner. Don’t say we are boarding on time ten minutes before the boarding time when the aircraft isn’t arriving for another forty minutes.

Took off on time and successfully avoided weather that looked to be a problem along the way

I liked everything. Except that my neck was hurting on the seat. I couldn't sleep.

We were delayed Al ost / hours after boarding so that maintenance had to add oil to the engines. Then the oil they grabbed had been left out in the Dallas record cold and was frozen. They had to go back to the hanger and grab some that was not frozen.

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