$288 Find Cheap Flights from Harlingen to Caribbean - Compare and Save

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 10/31. 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
Oranjestad
Oranjestad2 stops$826
Nassau
Nassau1 stop$648
Oranjestad
Oranjestad2 stops$826
Nassau
Nassau1 stop$648

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

Sat, Oct 31 - Sat, Nov 7
United Airlines Logo
7:18 am - 3:36 pm
HRL
-
SJU
7h 18m
1 stop
United Airlines Logo
8:05 am - 7:43 pm
SJU
-
HRL
13h 38m
2 stops
$288United Airlines
Sat, Oct 24 - Tue, Oct 27
United Airlines Logo
5:05 am - 3:42 pm
HRL
-
SJU
9h 37m
1 stop
United Airlines Logo
6:40 am - 4:00 pm
SJU
-
HRL
10h 20m
1 stop
$305United Airlines
Sat, Oct 31 - Sat, Nov 7
United Airlines Logo
5:05 am - 3:36 pm
HRL
-
SJU
9h 31m
1 stop
United Airlines Logo
7:40 am - 4:00 pm
SJU
-
HRL
10h 20m
1 stop
$339United Airlines
Sat, Oct 24 - Tue, Oct 27
American Airlines Logo
6:42 pm - 3:38 pm
HRL
-
SJU
19h 56m
2 stops
American Airlines Logo
2:18 pm - 10:08 am
SJU
-
HRL
20h 50m
2 stops
$350American Airlines
Sat, Oct 31 - Sat, Nov 7
United Airlines Logo
7:18 am - 11:36 pm
HRL
-
SJU
15h 18m
2 stops
United Airlines Logo
8:05 am - 7:43 pm
SJU
-
HRL
13h 38m
2 stops
$387United Airlines
Sat, Oct 24 - Tue, Oct 27
United Airlines Logo
7:15 am - 11:50 pm
HRL
-
SJU
15h 35m
2 stops
United Airlines Logo
12:00 pm - 10:51 pm
SJU
-
HRL
11h 51m
2 stops
$405United Airlines
Sat, Oct 24 - Wed, Oct 28
United Airlines Logo
5:05 am - 3:42 pm
HRL
-
SJU
9h 37m
1 stop
United Airlines Logo
6:40 am - 4:00 pm
SJU
-
HRL
10h 20m
1 stop
$409United Airlines
Sat, Oct 24 - Tue, Oct 27
American Airlines Logo
6:42 pm - 3:38 pm
HRL
-
SJU
19h 56m
2 stops
American Airlines Logo
6:00 am - 6:12 pm
SJU
-
HRL
13h 12m
1 stop
$429American Airlines
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
7:00 am - 7:20 pm
HRL
-
SJU
11h 20m
2 stops
Southwest Logo
6:25 am - 3:50 pm
SJU
-
HRL
10h 25m
2 stops
$433Southwest
Fri, Sep 4 - Wed, Sep 9
Southwest Logo
10:55 am - 10:10 pm
HRL
-
SJU
10h 15m
2 stops
Southwest Logo
1:20 pm - 9:45 pm
SJU
-
HRL
9h 25m
2 stops
$446Southwest
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 is the cheapest month to fly from Harlingen to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Harlingen to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Harlingen to Caribbean is May, when tickets cost $309 (return) on average. On the other hand, the most expensive months are December and October, when the average cost of round-trip tickets is $1,051 and $1,032 respectively.

Good to know

Low season

March

Cheapest flight

$288
Best time to beat the crowds but there is an average 18% 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.

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 4242 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

8.0 ExcellentRobyn, Jul 2026
HOU - DEN
Read more Southwest reviews

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

Great job! My family doesnt fly often but we felt safe 100%

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

I don't know why flying out of Sarasota requires two plane changes.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

Unbelievably smooth boarding at IAH and the flight attendants were top notch.

We flew business fares. Was amazing. However, the check in didn't offer business fares preboarding which is less hectic. 8/10 due to this. Staff compared to Canadian carriers go above and beyond. Would gladly fly United again.

Comfortable seating POS to IAH. Food options were satisfactory. Good seat from IAH to ANC. Food options could be better.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

There could have been better food options in economy on the long 7hr trip from IAH to AM.

It was terribly delayed with zero support from united airlines. I reached at 1 am in the night. They did not provide any option to change the flights.

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

The entertainment is a bit limited, it would be better if they added some games to play besides the movies and tv shows. But the seats are comfortable and the crew is polite

the seat was not padded at all - uncomfortable after a 3 hour flight

This flight was of course delayed because American cannot have flights that are not delayed.

I sat at the airport all night from 8 pm until midnight. The airline kept delaying the flight. They also kept moving us to different gates - 4 times. Then they told us we didn’t have a pilot so we had to wait. Then they cancelled the flight at midnight! I ended up having to rent a car to drive home. So i ended up not even being able to fly on the flight i paid for. Ridiculous, and no agents could help at all. I will not ever book this flight.

Mechanical delay > Crew Time out. No communication to passengers. Crew time out was positioned as a surprise (even though it must have been know at the time of boarding that the crew would time out.

Upgraded to first class. I would consider the first class on that plane to be only slightly more comfortable than coach. Long delay.

How is it that every American flight from DFW to IND is significantly delayed? This is the third time in two months I have been delayed flying out of DFW - ALWAYS for a maintenance issue. Makes me want to drop flying American altogether…or maybe flying through Dallas. Miserable experience.

Initial flight had an engine overheat - returned to DFW. Had another plane ready, but crew timed out. Had to wait 5h for boarding. Fully boarded and pilot says plane is not flight worthy. Deplane and go to the other end of the terminal. Wait an hour to board third plane because the crew couldn’t leave the second plane because no wheelchairs were brought to remove passengers. Finally take off and there is no catering (in flight service) even in first class. Very much an AA failure.

We were delayed due to a mechanical issue, but the gate staff and then later captain were giving thorough and frequent updates. Ended up being delayed about an hour, but we did get out, so it was overall a good flight!

Comfort in premium economy is worth it for long hauls especially on the 787-9P Dreamliner with the modern updates. The food was okay. All 4 of us selected the same meal, 2 of us had very dry hard to cut chicken, the other 2 were tender and good. The sides/salad/dessert all very good as far as airline food goes. Crew were very attentive. Will be hard to ever go back to regular economy!

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports