$235 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 5/13. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Harlingen to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Oranjestad
Oranjestad2 stops$802
Nassau
Nassau1 stop$438
Oranjestad
Oranjestad2 stops$802
Nassau
Nassau1 stop$438

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 13 - Tue, Aug 18
American Airlines Logo
8:03 pm - 4:03 pm
HRL
-
SJU
19h 00m
2 stops
American Airlines Logo
4:53 pm - 10:04 am
SJU
-
HRL
18h 11m
2 stops
$330American Airlines
Thu, Aug 13 - Tue, Aug 18
American Airlines Logo
8:03 pm - 2:54 pm
HRL
-
SJU
17h 51m
1 stop
American Airlines Logo
6:00 am - 2:42 pm
SJU
-
HRL
9h 42m
2 stops
$410American Airlines
Wed, May 13 - Sat, May 16
American Airlines Logo
8:03 pm - 4:32 am
HRL
-
SJU
7h 29m
1 stop
American Airlines Logo
5:45 am - 10:51 pm
SJU
-
HRL
18h 06m
2 stops
$415American Airlines
Tue, May 12 - Tue, May 19
United Airlines Logo
7:00 am - 1:47 pm
HRL
-
NAS
5h 47m
1 stop
United Airlines Logo
2:53 pm - 8:00 pm
NAS
-
HRL
6h 07m
1 stop
$438United Airlines
Tue, May 12 - Tue, May 19
Southwest Logo
7:10 am - 6:30 pm
HRL
-
NAS
10h 20m
2 stops
Southwest Logo
2:10 pm - 10:00 pm
NAS
-
HRL
8h 50m
2 stops
$442Southwest
Tue, May 12 - Tue, May 19
American Airlines Logo
6:00 am - 2:46 pm
HRL
-
NAS
7h 46m
2 stops
American Airlines Logo
3:44 pm - 10:51 pm
NAS
-
HRL
8h 07m
1 stop
$462American Airlines
Wed, May 13 - Sat, May 16
Southwest Logo
12:45 pm - 11:40 pm
HRL
-
SJU
9h 55m
2 stops
Southwest Logo
9:40 am - 9:35 pm
SJU
-
HRL
12h 55m
2 stops
$507Southwest
Sat, Aug 1 - Tue, Aug 4
Southwest Logo
6:00 am - 8:35 pm
HRL
-
SJU
13h 35m
1 stop
Southwest Logo
11:50 am - 8:10 pm
SJU
-
HRL
9h 20m
2 stops
$508Southwest
Thu, Aug 13 - Tue, Aug 18
United Airlines Logo
5:15 am - 3:42 pm
HRL
-
SJU
9h 27m
1 stop
United Airlines Logo
7:00 am - 3:34 pm
SJU
-
HRL
9h 34m
1 stop
$523United Airlines
Wed, May 13 - Sat, May 16
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
$551United Airlines
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$235
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 29% lower on average.
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 4331 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

The new boarding process was easy and straightforward. Very pleasant.

10.0 ExcellentAnonymous, Apr 2026
LAS - OKC
Read more Southwest reviews

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

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.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

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's a long flight and I would have liked better snacks between lunch and the arrival meal. It's fine to have fruit and nuts but I really don't like ramen because it's salty junk soup. I'd suggest sandwiches. They're not expensive nor are they hard to store for a long flight. The FA's had a couple of big services and they were super busy preparing, executing and then cleaning up. Then they disappeared.

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

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.

The plane was very creaky and lots of ringing. Plane was dirty and dingy. I couldn't hear the captain's announcements from the flight deck. Not sure if it was the captain or the audio equipment, but good thing there wasn't an emergency where we needed clear instructions. The overhead compartments were clearly full, but the flight crew allowed people to stand in the back with their carry on luggage. Then after everyone boarded, they had to go to the front to gate check their luggage because there was no room for their bags and then they returned to their seats...such a waste of time when clearly the overhead compartments were full when they originally boarded.

The WiFi would not connect enough for me to do my actual work. It permaspooled, disconnected, said it was connected, then wouldn't open an email... it was frustrating. I am not a tall person, 5'4" - and I felt cramped with little room to reach into my bag under the seat in front of me. I feel sorry for anyone taller than me having to fly. the one positive thing I will add, is the overhead bins are roomy enough to manage more bags than other carriers.

Boarding was quick and efficient. We arrived at our destination early.

Seat was VERY uncomfortable. Flight was delayed and then boarded slowly. The crew was super helpful with boarding and supporting maximizing the luggage in the overhead.

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports