$155 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 9/15. 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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Cheap Flights from Harlingen to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Nassau
Nassau2 stops$574
Nassau
Nassau2 stops$574

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, Nov 3 - Fri, Nov 7
American Airlines Logo
6:38 pm - 1:41 pmHRL-SJU
17h 03m2 stops
American Airlines Logo
6:42 pm - 11:40 amSJU-HRL
18h 58m2 stops
$219American Airlines
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Wed, Sep 17 - Sat, Sep 20
American Airlines Logo
6:35 pm - 2:15 pmHRL-SJU
18h 40m1 stop
American Airlines Logo
1:40 pm - 9:41 amSJU-HRL
21h 01m2 stops
$347American Airlines
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Mon, Sep 22 - Fri, Sep 26
United Airlines Logo
7:00 am - 3:42 pmHRL-SJU
7h 42m1 stop
United Airlines Logo
2:55 pm - 11:18 pmSJU-HRL
9h 23m1 stop
$357United Airlines
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Tue, Sep 16 - Tue, Sep 23
United Airlines Logo
5:00 am - 3:42 pmHRL-SJU
9h 42m1 stop
United Airlines Logo
2:55 pm - 9:52 pmSJU-HRL
7h 57m1 stop
$417United Airlines
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Sun, Sep 14 - Wed, Sep 17
American Airlines Logo
6:19 pm - 12:47 pmHRL-SJU
17h 28m2 stops
American Airlines Logo
1:37 pm - 9:41 amSJU-HRL
21h 04m2 stops
$427American Airlines
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Tue, Oct 7 - Fri, Oct 10
United Airlines Logo
5:00 am - 3:42 pmHRL-SJU
9h 42m1 stop
United Airlines Logo
1:05 am - 9:16 pmSJU-HRL
21h 11m2 stops
$459United Airlines
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Tue, Sep 16 - Tue, Sep 23
United Airlines Logo
7:00 am - 11:57 pmHRL-SJU
15h 57m2 stops
United Airlines Logo
2:55 pm - 9:52 pmSJU-HRL
7h 57m1 stop
$465United Airlines
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Sat, Nov 1 - Wed, Nov 5
American Airlines Logo
5:25 am - 2:25 pmHRL-SJU
8h 00m1 stop
American Airlines Logo
4:19 pm - 11:14 pmSJU-HRL
8h 55m1 stop
$467American Airlines
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Wed, Sep 17 - Sun, Sep 21
Southwest Logo
7:25 am - 10:45 pmHRL-SJU
14h 20m2 stops
Southwest Logo
5:45 am - 3:25 pmSJU-HRL
10h 40m2 stops
$539Southwest
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Sat, Nov 1 - Tue, Nov 4
 Logo
5:00 am - 6:20 pmHRL-SJU
12h 20m2 stops
 Logo
2:05 am - 9:54 pmSJU-HRL
21h 49m2 stops
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 Sundays and the most expensive ones on Saturdays.

Good to know

Cheapest flight$155
Most popular time to fly with an average 12% 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 4246 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

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”.

Overall it was good. I missed my connection but I was put on another flight.

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.

Delayed flight that lead to a missed connection and a 5-hour trip became a 12-hour flight 🙄

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Great flight. No issues at all. I still think boarding could be more efficient but otherwise, a good experience.

Crew should be nicer and emphatic with customers. Same cookies as the past 20 years. Seat are ok and the plane was clean though it was delayed.

Very poor delay in dfw was really bad n long

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Flight was delayed again and again ultimately almost three hours getting us to our location at close to midnight by the time we got in and out of airport to destination. I had taken time off work to enjoy an evening at destination and that was now wasted

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.

Everything you need to know for your flight to Caribbean

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