$122 Find Cheap Flights from Harlingen to Caribbean Islands - Compare and Save

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 8/30. 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
Nassau
Nassau2 stops$733
Nassau
Nassau2 stops$733

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

Fri, Aug 21 - Tue, Aug 25
American Airlines Logo
6:43 pm - 2:38 pm
HRL
-
SJU
18h 55m
2 stops
American Airlines Logo
7:24 pm - 10:04 am
SJU
-
HRL
15h 40m
2 stops
$228American Airlines
Fri, Aug 14 - Fri, Aug 21
American Airlines Logo
6:43 pm - 2:38 pm
HRL
-
SJU
18h 55m
2 stops
American Airlines Logo
5:10 pm - 10:04 am
SJU
-
HRL
17h 54m
2 stops
$232American Airlines
Sat, Oct 24 - Tue, Oct 27
United Airlines Logo
5:05 am - 3:42 pm
HRL
-
SJU
9h 37m
1 stop
United Airlines Logo
1:05 am - 3:34 pm
SJU
-
HRL
15h 29m
2 stops
$255United Airlines
Sat, Oct 24 - Tue, Oct 27
United Airlines Logo
5:05 am - 3:42 pm
HRL
-
SJU
9h 37m
1 stop
United Airlines Logo
1:05 am - 3:34 pm
SJU
-
HRL
15h 29m
2 stops
$269United Airlines
Tue, Sep 22 - Tue, Sep 29
United Airlines Logo
7:15 am - 3:12 pm
HRL
-
SJU
6h 57m
1 stop
United Airlines Logo
7:00 am - 3:59 pm
SJU
-
HRL
9h 59m
1 stop
$271United Airlines
Sat, Oct 24 - Tue, Oct 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
$318United Airlines
Tue, Oct 13 - Fri, Oct 16
United Airlines Logo
5:05 am - 3:42 pm
HRL
-
SJU
9h 37m
1 stop
United Airlines Logo
7:00 am - 3:59 pm
SJU
-
HRL
9h 59m
1 stop
$329United Airlines
Mon, Aug 24 - Fri, Aug 28
American Airlines Logo
6:43 pm - 2:38 pm
HRL
-
SJU
18h 55m
2 stops
American Airlines Logo
6:00 am - 10:54 pm
SJU
-
HRL
17h 54m
2 stops
$330American Airlines
Fri, Aug 21 - Tue, Aug 25
United Airlines Logo
7:15 am - 3:42 pm
HRL
-
SJU
7h 27m
1 stop
United Airlines Logo
7:00 am - 1:24 pm
SJU
-
HRL
7h 24m
1 stop
$331United Airlines
Sat, Oct 24 - Tue, Oct 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
$348United Airlines
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 $374, prices are generally cheapest when you fly direct.

Good to know

Low seasonDecember
Cheapest flight$122
Best time to beat the crowds but there is an average 63% increase in price.
Most popular time to fly with an average 5% 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 11645 reviews
6.9Entertainment
7.9Crew
7.2Comfort
6.4Food
7.5Boarding
Airline reviews

Another uncoordinated American experience. Always surprises me at DFW for them of all places. Have to take this flight as there are no other good time options. We knew from the start that something was wrong, but the pilot wouldn't tell us. I just watched my Kayak app grow the delay by 10 minutes as it went to 3.5 hours. They were uncoordinated with maintenance (as maintenance, when finally arriving, knew within 15 minutes the plane wasn't going. No 'sorry' or 'this is what is going on' comment. The pilot seemed unfazed / didn't care about the process we were going through.

2.0 MediocreJarrod, Jun 2026
DFW - CVG
Read more American Airlines reviews

Another uncoordinated American experience. Always surprises me at DFW for them of all places. Have to take this flight as there are no other good time options. We knew from the start that something was wrong, but the pilot wouldn't tell us. I just watched my Kayak app grow the delay by 10 minutes as it went to 3.5 hours. They were uncoordinated with maintenance (as maintenance, when finally arriving, knew within 15 minutes the plane wasn't going. No 'sorry' or 'this is what is going on' comment. The pilot seemed unfazed / didn't care about the process we were going through.

The seats. The seat in front of me was awful and when the guy sat down, it flew back and hit my head when I was putting my backpack under the seat, It didn't make for a pleasant experience,

The flight back to Dallas was delayed, which has happened to me several times with American Airlines. There was no announcement, no update sent out, no compensation offered for the inconvenience.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports