$221 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 6/11. 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
Nassau
Nassau2 stops$455
Nassau
Nassau2 stops$455

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, Mar 30 - Wed, Apr 8
American Airlines Logo
8:06 pm - 2:50 pm
HRL
-
SJU
17h 44m
2 stops
American Airlines Logo
7:00 pm - 10:17 am
SJU
-
HRL
16h 17m
2 stops
$370American Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
12:10 pm - 8:38 pm
HRL
-
SJU
7h 28m
1 stop
United Airlines Logo
7:20 am - 8:00 pm
SJU
-
HRL
13h 40m
2 stops
$395United Airlines
Mon, Mar 30 - Wed, Apr 8
American Airlines Logo
8:06 pm - 2:11 pm
HRL
-
SJU
17h 05m
1 stop
American Airlines Logo
7:00 pm - 10:17 am
SJU
-
HRL
16h 17m
2 stops
$410American Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
12:10 pm - 8:38 pm
HRL
-
SJU
7h 28m
1 stop
United Airlines Logo
7:20 am - 8:00 pm
SJU
-
HRL
13h 40m
2 stops
$430United Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
12:10 pm - 8:38 pm
HRL
-
SJU
7h 28m
1 stop
United Airlines Logo
7:00 am - 4:04 pm
SJU
-
HRL
10h 04m
1 stop
$433United Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
12:10 pm - 8:38 pm
HRL
-
SJU
7h 28m
1 stop
United Airlines Logo
2:55 pm - 9:59 pm
SJU
-
HRL
8h 04m
1 stop
$435United Airlines
Thu, Apr 23 - Wed, Apr 29
American Airlines Logo
2:47 pm - 9:13 am
HRL
-
SJU
17h 26m
2 stops
American Airlines Logo
11:59 pm - 10:17 am
SJU
-
HRL
11h 18m
1 stop
$450American Airlines
Mon, Jun 15 - Wed, Jun 24
Southwest Logo
1:00 pm - 12:25 am
HRL
-
SJU
10h 25m
1 stop
Southwest Logo
6:30 am - 12:05 pm
SJU
-
HRL
6h 35m
1 stop
$456Southwest
Mon, Jun 15 - Wed, Jun 24
Southwest Logo
11:35 am - 11:35 pm
HRL
-
SJU
11h 00m
2 stops
Southwest Logo
11:15 am - 8:50 pm
SJU
-
HRL
10h 35m
2 stops
$479Southwest
Sun, May 24 - Thu, Jun 4
Southwest Logo
7:55 am - 6:30 pm
HRL
-
NAS
9h 35m
2 stops
Southwest Logo
8:45 am - 9:40 pm
NAS
-
HRL
13h 55m
2 stops
$555Southwest
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$221
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 4298 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

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!!

10.0 ExcellentTy&Steph, Feb 2026
CLT - STL
Read more Southwest reviews

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.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

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

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

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!

We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.

The seats are too uncomfortable for anyone over 5ft 8in. I'm 5'10" with a back and hip issue and I was in pai for the full duration of the flight.

Flight was on time and the meal and service were good.

The accessible bathroom should be visible to people in Economy class.

Lexus in first class was absolutely amazing! Beat flight attendant i’ve ever seen.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports