$311 Find Cheap Flights from Harlingen to Caribbean Islands

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 Islands departing on 8/20. 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
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.

Bundle and saveSave money when you bundle your flight + hotel.

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

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Harlingen to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Nassau
Nassau2 stops$576
Santiago de los Caballeros
Santiago de los Caballeros2 stops$1,049
Nassau
Nassau2 stops$576
Santiago de los Caballeros
Santiago de los Caballeros2 stops$1,049

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

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
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 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
Mon, May 11 - Mon, May 18
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
$556American Airlines
Tue, Jun 30 - Fri, Jul 3
Southwest Logo
7:05 am - 6:30 pm
HRL
-
NAS
10h 25m
2 stops
Southwest Logo
8:45 am - 9:40 pm
NAS
-
HRL
13h 55m
2 stops
$576Southwest
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
Tue, Jun 30 - Fri, Jul 3
United Airlines Logo
5:10 am - 3:56 pm
HRL
-
NAS
9h 46m
1 stop
United Airlines Logo
2:53 pm - 7:49 pm
NAS
-
HRL
5h 56m
1 stop
$596United Airlines
Tue, Jun 30 - Fri, Jul 3
American Airlines Logo
6:00 am - 5:04 pm
HRL
-
NAS
10h 04m
1 stop
American Airlines Logo
6:45 pm - 10:12 am
NAS
-
HRL
16h 27m
2 stops
$600American Airlines
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
5:00 pm - 12:45 am
HRL
-
SJU
6h 45m
1 stop
Southwest Logo
6:00 am - 4:15 pm
SJU
-
HRL
11h 15m
2 stops
$641Southwest
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 $346, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonOctober
Cheapest flight$311
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 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 11681 reviews
6.9Entertainment
7.9Crew
6.4Food
7.2Comfort
7.5Boarding
Airline reviews

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

6.0 GoodFred, Apr 2026
DFW - IND
Read more American Airlines reviews

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 Islands

Information on your arrival and departure airports

Harlingen (HRL)