$343 Find Cheap Flights from Harlingen to Caribbean Islands

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 Islands departing on 3/23. 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 Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Harlingen to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Harlingen to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Harlingen to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Oranjestad
Oranjestad2 stops$816
Nassau
Nassau1 stop$469
Santiago de los Caballeros
Santiago de los Caballeros2 stops$748
Oranjestad
Oranjestad2 stops$816
Nassau
Nassau1 stop$469
Santiago de los Caballeros
Santiago de los Caballeros2 stops$748

Book Cheap Harlingen to Caribbean Islands 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 Islands 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 Islands

Mon, Apr 13 - Tue, Apr 21
United Airlines Logo
12:05 pm - 8:38 pm
HRL
-
SJU
7h 33m
1 stop
United Airlines Logo
1:00 am - 4:04 pm
SJU
-
HRL
16h 04m
2 stops
$343United Airlines
Mon, Apr 13 - Wed, Apr 22
United Airlines Logo
12:05 pm - 8:38 pm
HRL
-
SJU
7h 33m
1 stop
United Airlines Logo
7:00 am - 4:04 pm
SJU
-
HRL
10h 04m
1 stop
$371United Airlines
Mon, May 11 - Thu, May 14
American Airlines Logo
2:51 pm - 10:53 am
HRL
-
SJU
19h 02m
2 stops
American Airlines Logo
11:59 pm - 10:17 am
SJU
-
HRL
11h 18m
1 stop
$384American Airlines
Mon, May 25 - Tue, Jun 2
American Airlines Logo
8:04 pm - 4:25 am
HRL
-
SJU
7h 21m
1 stop
American Airlines Logo
7:15 pm - 10:13 am
SJU
-
HRL
15h 58m
2 stops
$390American Airlines
Mon, Apr 13 - Wed, Apr 22
Southwest Logo
10:40 am - 11:25 pm
HRL
-
SJU
11h 45m
2 stops
Southwest Logo
2:00 pm - 10:00 pm
SJU
-
HRL
9h 00m
2 stops
$400Southwest
Mon, May 11 - Sat, May 16
American Airlines Logo
2:51 pm - 10:53 am
HRL
-
SJU
19h 02m
2 stops
American Airlines Logo
5:45 am - 10:51 pm
SJU
-
HRL
18h 06m
2 stops
$409American Airlines
Wed, Apr 8 - Wed, Apr 15
American Airlines Logo
8:03 pm - 4:32 am
HRL
-
SJU
7h 29m
1 stop
American Airlines Logo
7:00 pm - 10:17 am
SJU
-
HRL
16h 17m
2 stops
$429American Airlines
Mon, May 11 - Thu, May 14
Southwest Logo
10:40 am - 11:25 pm
HRL
-
SJU
11h 45m
2 stops
Southwest Logo
2:00 pm - 11:00 pm
SJU
-
HRL
10h 00m
2 stops
$445Southwest
Mon, Apr 27 - Thu, Apr 30
Air Canada Logo
9:20 am - 12:25 pm
HRL
-
NAS
26h 05m
2 stops
Air Canada Logo
9:10 pm - 11:23 am
NAS
-
HRL
39h 13m
2 stops
$1,176Air Canada
Mon, Apr 27 - Thu, Apr 30
Air Canada Logo
9:20 am - 12:25 pm
HRL
-
NAS
26h 05m
2 stops
Air Canada Logo
9:10 pm - 11:23 am
NAS
-
HRL
39h 13m
2 stops
$1,177Air Canada
Booking Insights

KAYAK's insights & trends for Harlingen to Caribbean Islands flights

Get data-powered insights and trends into flights from Harlingen to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Harlingen to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $383, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Harlingen to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Harlingen to Caribbean Islands, 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 Islands 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.

Find deals

Good to know

Low seasonApril
Cheapest flight$305
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 Islands flights

  • How does KAYAK find such low prices on flights from Harlingen to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Harlingen to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Harlingen to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Harlingen to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Harlingen to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Harlingen to Caribbean Islands? 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.
7.1
American AirlinesOverall score based on 11464 reviews
7.9Crew
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
Airline reviews

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.

6.0 GoodAnna, Mar 2026
DFW - MIA
Read more American Airlines reviews

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.

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Harlingen (HRL)