$250 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 10/21. 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

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 - Tue, Aug 25
United Airlines Logo
5:15 am - 3:42 pm
HRL
-
SJU
9h 27m
1 stop
United Airlines Logo
2:20 pm - 9:44 pm
SJU
-
HRL
8h 24m
1 stop
$311United Airlines
Thu, Aug 20 - Tue, Aug 25
United Airlines Logo
5:15 am - 3:42 pm
HRL
-
SJU
9h 27m
1 stop
United Airlines Logo
2:20 pm - 9:44 pm
SJU
-
HRL
8h 24m
1 stop
$329United Airlines
Thu, Aug 20 - Tue, Aug 25
American Airlines Logo
8:03 pm - 2:38 pm
HRL
-
SJU
17h 35m
2 stops
American Airlines Logo
4:53 pm - 10:04 am
SJU
-
HRL
18h 11m
2 stops
$330American Airlines
Thu, Aug 6 - Fri, Aug 14
American Airlines Logo
8:03 pm - 2:38 pm
HRL
-
SJU
17h 35m
2 stops
American Airlines Logo
6:00 am - 10:54 pm
SJU
-
HRL
17h 54m
2 stops
$407American Airlines
Thu, Aug 20 - Tue, Aug 25
American Airlines Logo
8:03 pm - 2:54 pm
HRL
-
SJU
17h 51m
1 stop
American Airlines Logo
4:53 pm - 10:04 am
SJU
-
HRL
18h 11m
2 stops
$410American Airlines
Thu, Aug 20 - Tue, Aug 25
United Airlines Logo
5:15 am - 3:42 pm
HRL
-
SJU
9h 27m
1 stop
United Airlines Logo
2:20 pm - 9:44 pm
SJU
-
HRL
8h 24m
1 stop
$419United Airlines
Thu, Aug 6 - Fri, Aug 14
American Airlines Logo
8:03 pm - 2:38 pm
HRL
-
SJU
17h 35m
2 stops
American Airlines Logo
3:44 pm - 10:54 pm
SJU
-
HRL
8h 10m
1 stop
$523American Airlines
Mon, May 11 - Thu, May 14
American Airlines Logo
10:47 am - 11:03 pm
HRL
-
SJU
11h 16m
1 stop
American Airlines Logo
6:45 am - 2:21 pm
SJU
-
HRL
8h 36m
1 stop
$556American Airlines
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
2:10 pm - 12:15 am
HRL
-
SJU
9h 05m
2 stops
Southwest Logo
6:00 am - 4:15 pm
SJU
-
HRL
11h 15m
2 stops
$591Southwest
Mon, May 11 - Mon, May 18
American Airlines Logo
6:00 am - 9:24 pm
HRL
-
SJU
14h 24m
2 stops
American Airlines Logo
5:45 am - 10:51 pm
SJU
-
HRL
18h 06m
2 stops
$596American 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 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$250
Best time to beat the crowds but there is an average 62% increase in price.
Most popular time to fly and prices are also 30% 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 4314 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

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

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

The staff was nice. I appreciated that I was able to take an earlier flight, even though it was last minute. The boarding process felt rather chaotic.

My flight got delayed a total of five times. And the boarding gate changed four times. most of the time the platform was not up-to-date with the changes taking place. The most discouraging part of the entire trip by far.

Returned home with a blood clot from flight homes and the uncomfortable aircraft I was on.

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

Everything was delayed and the staff sent me to the wrong gate, causing me to miss one of my flights. I arrived at my destination 6 hours later than I was supposed to.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

It was really a terrific experience both going and returning on AA. Staff and crew were professional.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports