$179 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

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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
Oranjestad1 stop$686
Nassau
Nassau2 stops$474
Oranjestad
Oranjestad1 stop$686
Nassau
Nassau2 stops$474

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

Tue, Oct 27 - Tue, Nov 3
United Airlines Logo
7:10 am - 3:36 pm
HRL
-
SJU
7h 26m
1 stop
United Airlines Logo
2:05 am - 4:01 pm
SJU
-
HRL
15h 56m
2 stops
$288United Airlines
Tue, Oct 27 - Wed, Nov 4
United Airlines Logo
5:05 am - 3:36 pm
HRL
-
SJU
9h 31m
1 stop
United Airlines Logo
7:40 am - 1:21 pm
SJU
-
HRL
7h 41m
1 stop
$288United Airlines
Tue, Oct 27 - Wed, Nov 4
United Airlines Logo
5:05 am - 3:36 pm
HRL
-
SJU
9h 31m
1 stop
United Airlines Logo
8:05 am - 7:47 pm
SJU
-
HRL
13h 42m
2 stops
$288United Airlines
Sat, Oct 24 - Tue, Oct 27
American Airlines Logo
2:47 pm - 11:31 am
HRL
-
SJU
19h 44m
2 stops
American Airlines Logo
2:18 pm - 10:08 am
SJU
-
HRL
20h 50m
2 stops
$350American Airlines
Tue, Oct 27 - Wed, Nov 4
American Airlines Logo
5:50 am - 3:23 pm
HRL
-
SJU
8h 33m
1 stop
American Airlines Logo
4:59 pm - 10:13 am
SJU
-
HRL
19h 14m
1 stop
$350American Airlines
Tue, Oct 27 - Wed, Nov 4
American Airlines Logo
2:47 pm - 9:46 am
HRL
-
SJU
17h 59m
2 stops
American Airlines Logo
6:55 pm - 10:13 am
SJU
-
HRL
17h 18m
2 stops
$350American Airlines
Mon, Oct 26 - Sun, Nov 1
Southwest Logo
12:55 pm - 11:05 pm
HRL
-
SJU
9h 10m
2 stops
Southwest Logo
6:35 am - 4:05 pm
SJU
-
HRL
11h 30m
2 stops
$457Southwest
Sun, Jan 10 - Fri, Jan 15
Southwest Logo
7:40 am - 6:45 pm
HRL
-
SJU
9h 05m
2 stops
Southwest Logo
7:35 am - 5:30 pm
SJU
-
HRL
11h 55m
2 stops
$479Southwest
Sat, Jan 2 - Sat, Jan 9
Multiple Airlines Logo
5:05 am - 12:36 am
HRL
-
SJU
17h 31m
3 stops
Multiple Airlines Logo
7:15 am - 9:44 pm
SJU
-
HRL
16h 29m
2 stops
$3,019Multiple Airlines
Thu, Dec 24 - Fri, Jan 1
Multiple Airlines Logo
5:05 am - 12:36 am
HRL
-
SJU
17h 31m
3 stops
Multiple Airlines Logo
7:15 am - 9:48 pm
SJU
-
HRL
16h 33m
2 stops
$4,948Multiple 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 $357, prices are generally cheapest when you fly direct.

Good to know

Low season

September

Cheapest flight

$179
Best time to beat the crowds with an average 56% drop in price.
Most popular time to fly with an average 4% 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 11845 reviews
7.9Crew
6.4Food
6.8Entertainment
7.5Boarding
7.2Comfort
Airline reviews

Bad experience going to DFW with an IT outage then bad on the way back with a nearly 5 hour delay that’s started as maintenance then caused us to wait further due to weather - which would not have happened if we had left on time.

2.0 MediocreRebecca, Jul 2026
DFW - TPA
Read more American Airlines reviews

Bad experience going to DFW with an IT outage then bad on the way back with a nearly 5 hour delay that’s started as maintenance then caused us to wait further due to weather - which would not have happened if we had left on time.

Horrible experience flying with American. Flight was delayed due to inbound flight delay. Fine, it happens. Then, we were delayed an additional almost 30 minutes due to the paperwork for departure having a "clerical error." Then, upon landing at the destination airport we were stuck on the plane for an HOUR after we landed and pulled up to the gate because apparently there was another plane. An hour waiting for the gate 12:30 AM when the flight has already been delayed due to operational error feels like a complete failure of the ability to do the one thing they need to do apart from actually have the plane takeoff and land. Very disappointing.

It was a 3 hour flight from Dallas to Missoula. The aircraft did not have power plugs, internet or in-flight entertainment. When boarding, one flight attendant was "somewhere in the airport" so delayed the boarding process (not coming from another flight) although we did take off on time and landed early. In flight there was little to no service - we got the standard beverage but no real connection with the crew which feels unusual for a 3 hour flight. A passenger needed help stowing her bag and got no assistance, and actually some passive aggressive comments from the flight attendants about "she needs to remove the extender" and "she'll have to find a place for it". I have seen others be helpful and put a bag in the closet, or support assistance as the boarding door was already closed. Just not a great experience considering the cost of my round trip ticket {$1000}.

Horrible. No AC. No Air inside the plane. We had to deplane twice! It is late almost 5 hrs in total. I almost passed out and about to call 911. I asked the crew to be honest and open the door. The lady next to me was lay down in the floor due to heat and no air inside the plane. I got headaches, can’t wait the replacement flight about midnight Dallas time. I end it up rebook for next day flight and stay overnight using my own pocket in a hotel nearby due to headaches and can’t breath. I still have a headache this morning. Still not decided yes how to file this issue to AA and/or FAA.

Worst communication. Delayed boarding for two hours without a single announcement until hour 1 had passed - on time status showing until our flight was supposed to takeoff and the crew had already walked away. No one was boarding. Disgusting part of DFW overcrowded with no AC on a 97 degree day. Then the first app update is that we’d take off in 15 mins… but again no one had boarded a full flight. No announcement in the terminal so everyone is just crowded around a disgusting place with no info for over an hour which turned into two. This was an overfill flight and a disgrace to passenger decency all while likely just trying to fix their own issue of overbooking. The worst airline at the worst airport.

The flight was delayed almost three hours. I understand delays happen from time to time, but this flight was delayed no less than 10 times. I wish the amount of time of the delay was more accurate, versus delaying in 10 or 20 minute increments many, many times.

The flight was ok, i understand Houston-Dallas is a short distance. The plane is really small: no TV, no snacks, but other than that, all was good. We had a bid delay but luckily it did not affect my connection

boarding announcements werent clear/loud. Tired of those cookies. Of the 3 staff/attendants, 1 was good and the other 2 were mediocre.

It was good overall but when I book my flight and seat through Kayak, AA will at times change those seats during check-in time which I don’t understand why. I always book aisle seats and had to sit at window for my flight to Austin this trip.

the seat was not padded at all - uncomfortable after a 3 hour flight

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports