$141 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 4/13. 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

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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$726
Nassau
Nassau2 stops$457
Oranjestad
Oranjestad2 stops$726
Nassau
Nassau2 stops$457

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

Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
8:03 pm - 4:32 am
HRL
-
SJU
7h 29m
1 stop
American Airlines Logo
6:02 pm - 10:17 am
SJU
-
HRL
17h 15m
2 stops
$373American Airlines
Mon, Sep 14 - Fri, Sep 18
United Airlines Logo
7:27 am - 3:42 pm
HRL
-
SJU
7h 15m
1 stop
United Airlines Logo
7:00 am - 3:34 pm
SJU
-
HRL
9h 34m
1 stop
$385United Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
8:03 pm - 2:42 pm
HRL
-
SJU
17h 39m
1 stop
American Airlines Logo
6:02 pm - 10:17 am
SJU
-
HRL
17h 15m
2 stops
$400American Airlines
Mon, Sep 14 - Fri, Sep 18
Southwest Logo
10:55 am - 11:50 pm
HRL
-
SJU
11h 55m
2 stops
Southwest Logo
6:00 am - 4:05 pm
SJU
-
HRL
11h 05m
2 stops
$410Southwest
Sat, Apr 18 - Fri, Apr 24
United Airlines Logo
7:00 am - 11:50 pm
HRL
-
SJU
15h 50m
2 stops
United Airlines Logo
1:00 am - 4:04 pm
SJU
-
HRL
16h 04m
2 stops
$413United Airlines
Fri, Apr 17 - Tue, Apr 21
United Airlines Logo
7:00 am - 9:24 pm
HRL
-
SJU
13h 24m
2 stops
United Airlines Logo
7:20 am - 9:59 pm
SJU
-
HRL
15h 39m
2 stops
$440United Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
8:03 pm - 2:42 pm
HRL
-
SJU
17h 39m
1 stop
American Airlines Logo
11:59 pm - 10:17 am
SJU
-
HRL
11h 18m
1 stop
$453American Airlines
Thu, Jul 23 - Thu, Jul 30
Southwest Logo
7:10 am - 7:25 pm
HRL
-
SJU
11h 15m
2 stops
Southwest Logo
6:00 am - 6:00 pm
SJU
-
HRL
13h 00m
1 stop
$476Southwest
Mon, Apr 20 - Thu, Apr 23
Air Canada Logo
7:00 am - 12:25 pm
HRL
-
NAS
28h 25m
2 stops
Air Canada Logo
9:40 pm - 9:59 pm
NAS
-
HRL
25h 19m
2 stops
$1,110Air Canada
Mon, Apr 27 - Thu, Apr 30
Air Canada Logo
7:00 am - 12:25 pm
HRL
-
NAS
28h 25m
2 stops
Air Canada Logo
9:10 pm - 11:23 am
NAS
-
HRL
39h 13m
2 stops
$1,119Air 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 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$141
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 1% 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 4325 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

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

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.

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Poor communication ahead of time about flight delays and old planes/other equipment.

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

The crew was excellent and overall the flight was good. No complaints.

Like all of the flights I took to get down to Dallas. They were delayed

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports