$285 Find Cheap Flights from Harlingen to Caribbean

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 10/24. 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

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

Sa, Okt 24 - Mi, Okt 28
United Airlines Logo
5:05 am - 3:42 pm
HRL
-
SJU
9h 37m
1 stop
United Airlines Logo
7:30 am - 7:32 pm
SJU
-
HRL
13h 02m
2 stops
$285United Airlines
Sa, Okt 24 - Mi, Okt 28
United Airlines Logo
7:15 am - 3:42 pm
HRL
-
SJU
7h 27m
1 stop
United Airlines Logo
2:46 pm - 9:44 pm
SJU
-
HRL
7h 58m
1 stop
$309United Airlines
So, Aug 23 - Sa, Aug 29
American Airlines Logo
8:03 pm - 2:38 pm
HRL
-
SJU
17h 35m
2 stops
American Airlines Logo
5:47 pm - 10:04 am
SJU
-
HRL
17h 17m
2 stops
$330American Airlines
Sa, Okt 24 - Di, Okt 27
United Airlines Logo
5:05 am - 3:42 pm
HRL
-
SJU
9h 37m
1 stop
United Airlines Logo
2:46 pm - 9:44 pm
SJU
-
HRL
7h 58m
1 stop
$338United Airlines
Sa, Okt 24 - Di, Okt 27
American Airlines Logo
4:58 pm - 11:05 am
HRL
-
SJU
17h 07m
2 stops
American Airlines Logo
2:00 pm - 10:16 am
SJU
-
HRL
21h 16m
2 stops
$400American Airlines
Mo, Aug 17 - Mo, Aug 24
American Airlines Logo
6:43 pm - 12:48 pm
HRL
-
SJU
17h 05m
2 stops
American Airlines Logo
3:44 pm - 10:54 pm
SJU
-
HRL
8h 10m
1 stop
$443American Airlines
Mi, Jul 1 - Mi, Jul 8
American Airlines Logo
6:00 am - 5:04 pm
HRL
-
NAS
10h 04m
1 stop
American Airlines Logo
6:05 pm - 10:12 am
NAS
-
HRL
17h 07m
1 stop
$591American Airlines
Di, Nov 3 - Mi, Nov 4
Air Canada Logo
5:10 am - 8:25 pm
HRL
-
NAS
14h 15m
2 stops
Air Canada Logo
12:30 pm - 7:32 pm
NAS
-
HRL
32h 02m
2 stops
$1,341Air Canada
Di, Nov 3 - Mi, Nov 4
Air Canada Logo
5:10 am - 8:25 pm
HRL
-
NAS
14h 15m
2 stops
Air Canada Logo
12:30 pm - 7:32 pm
NAS
-
HRL
32h 02m
2 stops
$1,347Air Canada
Di, Nov 3 - Mi, Nov 4
Air Canada Logo
5:10 am - 8:25 pm
HRL
-
NAS
14h 15m
2 stops
Air Canada Logo
12:30 pm - 7:32 pm
NAS
-
HRL
32h 02m
2 stops
$1,391Air 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 January, when tickets cost $239 (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 seasonOctober
Cheapest flight$285
Best time to beat the crowds but there is an average 64% 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 4254 reviews
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

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

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

Boarded early, left early, arrived 40 mins early! A win win for me!

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

MY FAMILY'S LUGGAGE WAS LOST FROM ROME TO BARI. I WAS THE ONLY ONE THAT RECEIVED MY LUGGAGE FROM ROME TO BARI. AFTER DEPLANING IN BARI, WE WASTED A LOT OF TIME AT BAG CLAIMS LOST AND FOUND REPORTING THE CLAIM AND PLEADING FOR THE BAGS TO BE DELIVERED THE NEXT DAY. WE WERE TOLD THAT IT TAKES 3 DAYS MINIMUM TO DELIVER. MY DAUGHTER AND MY GIRLFRIEND NEEDED THEIR PERSONAL THINGS AND WE WERE STAYING 3 HOURS AWAY FROM THE BARI AIRPORT. WE HAD TO DRIVE 3 HOURS TO THE AIRPORT TO COLLECT OUR LOST LUGGAGE THE NEXT DAY. WE ARE NOT HAPPY WITH THE EXPERIENCE

We had a delay, but thankfully I made it to my connection. Overall it went smooth

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

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

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

The flight from Dallas to Tokyo was not on Japan Airlines. It was on American Airlines. Very disappointed that we did not fly on Japan Airlines. Will not be using you liars again. I’ll just book direct from the airline next time. Wish you could make this right and has us fly on Japan Air when heading back home to the US.

They made nearly everyone check their bag because the overhead bins are way too small. Extremely inconvenient

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

Movies on my phone are great. It would be nice to have a gluten free snack option.

They lost my baggage and I am still struggling to the information and update

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

Cancelled BOYH legs of our flight home 30 min before initial boarding

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports