$161 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 8/18. 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$687
Nassau
Nassau1 stop$611
Oranjestad
Oranjestad2 stops$687
Nassau
Nassau1 stop$611

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, Sep 19 - Wed, Sep 23
United Airlines Logo
7:27 am - 3:42 pm
HRL
-
SJU
7h 15m
1 stop
United Airlines Logo
2:20 pm - 9:44 pm
SJU
-
HRL
8h 24m
1 stop
$228United Airlines
Sat, Sep 19 - Tue, Sep 22
United Airlines Logo
7:27 am - 3:42 pm
HRL
-
SJU
7h 15m
1 stop
United Airlines Logo
1:00 am - 3:34 pm
SJU
-
HRL
15h 34m
2 stops
$254United Airlines
Sat, Apr 25 - Tue, Apr 28
United Airlines Logo
12:05 pm - 8:38 pm
HRL
-
SJU
7h 33m
1 stop
United Airlines Logo
1:00 am - 4:04 pm
SJU
-
HRL
16h 04m
2 stops
$299United Airlines
Sat, Sep 19 - Wed, Sep 23
American Airlines Logo
8:03 pm - 2:45 pm
HRL
-
SJU
17h 42m
2 stops
American Airlines Logo
2:05 pm - 10:16 am
SJU
-
HRL
21h 11m
2 stops
$330American Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
2:47 pm - 10:53 am
HRL
-
SJU
19h 06m
2 stops
American Airlines Logo
7:00 pm - 10:17 am
SJU
-
HRL
16h 17m
2 stops
$400American Airlines
Tue, May 5 - Mon, May 11
American Airlines Logo
6:45 pm - 3:20 pm
HRL
-
AUA
19h 35m
2 stops
American Airlines Logo
3:00 pm - 10:17 am
AUA
-
HRL
20h 17m
2 stops
$687American Airlines
Sun, Jun 28 - Thu, Jul 2
American Airlines Logo
4:57 pm - 2:44 pm
HRL
-
POP
20h 47m
2 stops
American Airlines Logo
3:45 pm - 4:50 pm
POP
-
HRL
26h 05m
2 stops
$761American Airlines
Sat, Apr 25 - Wed, Apr 29
Air Canada Logo
7:00 am - 8:05 pm
HRL
-
NAS
12h 05m
2 stops
Air Canada Logo
9:10 pm - 8:00 pm
NAS
-
HRL
23h 50m
2 stops
$1,147Air Canada
Sat, Apr 25 - Wed, Apr 29
Air Canada Logo
7:00 am - 12:55 pm
HRL
-
NAS
28h 55m
2 stops
Air Canada Logo
9:10 pm - 9:59 pm
NAS
-
HRL
25h 49m
2 stops
$1,149Air Canada
Sat, Apr 25 - Wed, Apr 29
Air Canada Logo
12:05 pm - 12:55 pm
HRL
-
NAS
23h 50m
2 stops
Air Canada Logo
1:50 pm - 8:00 pm
NAS
-
HRL
31h 10m
2 stops
$1,160Air 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 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 February, when tickets cost $347 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is $1,032 and $975 respectively.

Good to know

Low seasonApril
Cheapest flight$161
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 1% 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 4344 reviews
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

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

4.0 Okaysangeetha, Apr 2026
AUS - SJC
Read more Southwest reviews

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

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

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

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

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.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

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 !

I liked it better when you were truer to your roots Am paying more for less fun

The wheelchair service is useless. They live you in different spots, not tell you anything just wait. I waited 30 minutes in Frankfurt when decided to walk the 25 minutes distance. In Budapest nobody came.

Fine. The issues I had were associated with luggage being delayed from Turkey to Tanzania

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

We had excellent customer service despite the chaos at George Bush airport in Houston!

It isvvery small flight. No leg room . No space to put my personal item at feet.

Didn't make the flight because the first leg of my flight was canceled and the next leg was already booked.

Terrible because it was cancelled due to volcanic ash clouds in Guatemala while all other airlines kept flying. Had to pay for a hotel to stay overnight in Houston and try to fly next day.

Overall we had a good experience during our flight from San Francisco to Houston.

Airport terminal was outdated, flight was on a small jet with no wifi

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

The flight changed gates multiple times and flight had to be delayed multiple times

Delayed for mechanical and no updates on what was happening and how long the delay might be.

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Mostly good. The WiFi wasn’t working so that was not great.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Poor communication ahead of time about flight delays and old planes/other equipment.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports