$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 9/2. 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$745
Nassau
Nassau2 stops$431
Oranjestad
Oranjestad2 stops$745
Nassau
Nassau2 stops$431

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

Thu, Aug 20 - Mon, Aug 24
American Airlines Logo
5:25 am - 11:40 pm
HRL
-
SJU
17h 15m
2 stops
American Airlines Logo
4:49 pm - 9:32 am
SJU
-
HRL
17h 43m
2 stops
$290American Airlines
Wed, Apr 1 - Wed, Apr 8
American Airlines Logo
8:06 pm - 5:28 am
HRL
-
SJU
8h 22m
1 stop
American Airlines Logo
3:44 pm - 10:17 am
SJU
-
HRL
19h 33m
2 stops
$366American Airlines
Fri, Jun 12 - Tue, Jun 30
American Airlines Logo
4:57 pm - 9:39 am
HRL
-
SJU
15h 42m
2 stops
American Airlines Logo
7:15 pm - 7:34 pm
SJU
-
HRL
25h 19m
2 stops
$398American Airlines
Wed, Apr 8 - Wed, Apr 15
Southwest Logo
7:10 am - 6:10 pm
HRL
-
SJU
10h 00m
2 stops
Southwest Logo
5:35 am - 4:00 pm
SJU
-
HRL
11h 25m
2 stops
$452Southwest
Tue, May 5 - Tue, May 5
United Airlines Logo
12:10 pm - 8:38 pm
HRL
-
SJU
7h 28m
1 stop
United Airlines Logo
1:00 am - 4:04 pm
SJU
-
HRL
16h 04m
2 stops
$455United Airlines
Mon, Apr 20 - Mon, Apr 27
United Airlines Logo
7:00 am - 1:47 pm
HRL
-
NAS
5h 47m
1 stop
United Airlines Logo
2:53 pm - 7:40 pm
NAS
-
HRL
5h 47m
1 stop
$465United Airlines
Tue, May 5 - Tue, May 5
United Airlines Logo
12:10 pm - 8:38 pm
HRL
-
SJU
7h 28m
1 stop
United Airlines Logo
1:00 am - 4:04 pm
SJU
-
HRL
16h 04m
2 stops
$465United Airlines
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
6:55 am - 6:30 pm
HRL
-
NAS
10h 35m
2 stops
Southwest Logo
8:45 am - 11:00 pm
NAS
-
HRL
15h 15m
2 stops
$523Southwest
Tue, Apr 28 - Wed, Apr 29
United Airlines Logo
7:00 am - 1:47 pm
HRL
-
NAS
5h 47m
1 stop
United Airlines Logo
2:53 pm - 7:40 pm
NAS
-
HRL
5h 47m
1 stop
$532United Airlines
Sun, Jul 19 - Thu, Jul 23
Southwest Logo
6:30 am - 6:30 pm
HRL
-
NAS
11h 00m
2 stops
Southwest Logo
8:45 am - 9:40 pm
NAS
-
HRL
13h 55m
2 stops
$570Southwest
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 December and October, when the average cost of round-trip tickets is $1,475 and $1,032 respectively.

Good to know

Low seasonApril
Cheapest flight$158
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 5% 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 4310 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

WiFi was not working and didn’t have a beverage service

8.0 ExcellentNick, Mar 2026
BOS - MDW
Read more Southwest reviews

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

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.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

The power at the seat didn't work and the seat itself was difficult to adjust - this was a business class seat. Flight attendant gave me miles to compensate. The attendant was very professional and on top of his game the entire flight.

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

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

Never ontime and always delays. Long waits for customer service and often app doesn’t work

We arrived 25 minutes early only to be told our gate was occupied and so we sat for close to 30 minutes to pull into a gate. That’s not an early arrival!

The TSA check in took 1.5 hours to get through in Austin and I missed my flights back to DC

There was free WiFi (definitely a plus), but the flight was delayed 45 minutes waiting on a catering truck that never arrived. The pilot said there would be food vouchers given out at the end of the gangway to make up for the inconvenience, but there was no one offering those. Delay made me late for work!

Flight was on time and there was an empty seat next to me. That makes for a good flight!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports