$179 Find Cheap Flights from Harlingen to Caribbean - 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 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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Oranjestad
Oranjestad2 stops$826
Nassau
Nassau1 stop$470
Oranjestad
Oranjestad2 stops$826
Nassau
Nassau1 stop$470

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

Tue, Oct 27 - Wed, Nov 4
American Airlines Logo
2:46 pm - 1:28 pmHRL  Harlingen Valley Intl-SJU San Juan Luis Munoz Marin Intl
21h 42m2 stops Dallas/Fort Worth Miami
American Airlines Logo
6:28 am - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-HRL Harlingen Valley Intl
18h 31m1 stop Dallas/Fort Worth
$350American Airlines
Tue, Oct 27 - Wed, Nov 4
American Airlines Logo
2:46 pm - 9:46 amHRL  Harlingen Valley Intl-SJU San Juan Luis Munoz Marin Intl
18h 00m2 stops Dallas/Fort Worth Miami
American Airlines Logo
6:55 pm - 10:13 amSJU  San Juan Luis Munoz Marin Intl-HRL Harlingen Valley Intl
17h 18m2 stops Miami Dallas/Fort Worth
$350American Airlines
Tue, Oct 27 - Wed, Nov 4
American Airlines Logo
5:50 am - 3:23 pmHRL  Harlingen Valley Intl-SJU San Juan Luis Munoz Marin Intl
8h 33m1 stop Dallas/Fort Worth
American Airlines Logo
4:59 pm - 10:13 amSJU  San Juan Luis Munoz Marin Intl-HRL Harlingen Valley Intl
19h 14m1 stop Dallas/Fort Worth
$350American Airlines
Tue, Oct 27 - Wed, Nov 4
United Airlines Logo
5:05 am - 3:36 pmHRL  Harlingen Valley Intl-SJU San Juan Luis Munoz Marin Intl
9h 31m1 stop Houston George Bush Intcntl
United Airlines Logo
7:40 am - 4:01 pmSJU  San Juan Luis Munoz Marin Intl-HRL Harlingen Valley Intl
10h 21m1 stop Houston George Bush Intcntl
$378United Airlines
Tue, Sep 29 - Wed, Sep 30
United Airlines Logo
7:15 am - 3:42 pmHRL  Harlingen Valley Intl-SJU San Juan Luis Munoz Marin Intl
7h 27m1 stop Houston George Bush Intcntl
United Airlines Logo
1:00 am - 3:59 pmSJU  San Juan Luis Munoz Marin Intl-HRL Harlingen Valley Intl
15h 59m2 stops Newark Houston George Bush Intcntl
$443United Airlines
Sat, Oct 31 - Mon, Nov 2
United Airlines Logo
5:05 am - 1:33 pmHRL  Harlingen Valley Intl-NAS Nassau Intl
7h 28m1 stop Houston George Bush Intcntl
United Airlines Logo
2:40 pm - 10:48 pmNAS  Nassau Intl-HRL Harlingen Valley Intl
9h 08m1 stop Houston George Bush Intcntl
$470United Airlines
Sat, Jan 2 - Tue, Feb 2
Southwest Logo
5:35 am - 5:10 pmHRL  Harlingen Valley Intl-SJU San Juan Luis Munoz Marin Intl
9h 35m1 stop Houston Hobby
Southwest Logo
12:15 pm - 8:35 pmSJU  San Juan Luis Munoz Marin Intl-HRL Harlingen Valley Intl
10h 20m2 stops Orlando Austin Bergstrom
$491Southwest
Sat, Jan 2 - Tue, Feb 2
Southwest Logo
11:25 am - 12:15 amHRL  Harlingen Valley Intl-SJU San Juan Luis Munoz Marin Intl
10h 50m2 stops Austin Bergstrom Orlando
Southwest Logo
12:15 pm - 8:35 pmSJU  San Juan Luis Munoz Marin Intl-HRL Harlingen Valley Intl
10h 20m2 stops Orlando Austin Bergstrom
$539Southwest
Thu, Nov 19 - Fri, Nov 27
Air Canada Logo
5:05 am - 4:25 pmHRL  Harlingen Valley Intl-AUA Oranjestad Reina Beatrix
33h 20m2 stops Houston George Bush Intcntl Toronto Pearson Intl
Air Canada Logo
5:25 pm - 7:47 pmAUA  Oranjestad Reina Beatrix-HRL Harlingen Valley Intl
28h 22m2 stops Toronto Pearson Intl Houston George Bush Intcntl
$1,230Air Canada
Mon, Feb 1 - Thu, Feb 4
WestJet Logo
2:00 pm - 4:33 pmHRL  Harlingen Valley Intl-POP Puerto Plata La Union
24h 33m2 stops Minneapolis St Paul Toronto Pearson Intl
WestJet Logo
5:30 pm - 1:31 pmPOP  Puerto Plata La Union-HRL Harlingen Valley Intl
22h 01m2 stops Toronto Pearson Intl Minneapolis St Paul
$3,759WestJet
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 May, when tickets cost $309 (return) on average. On the other hand, the most expensive months are December and October, when the average cost of round-trip tickets is $1,051 and $1,032 respectively.

Good to know

Low season

March

Cheapest flight

$179
Best time to beat the crowds but there is an average 18% 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 4216 reviews
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

8.0 ExcellentSean, Jul 2026
Read more Southwest reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

Great job! My family doesnt fly often but we felt safe 100%

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

I don't know why flying out of Sarasota requires two plane changes.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

The experience with United Airlines was excellent; however, the experience with Houston Intercontinental Airport (IAH) was horrible. Although our flight departed from Terminal B, we had to go through security in Terminal C and then get on a train for travel to Terminal B. Additionally, there was significant walking required to get to the boarding location.

Unbelievably smooth boarding at IAH and the flight attendants were top notch.

We flew business fares. Was amazing. However, the check in didn't offer business fares preboarding which is less hectic. 8/10 due to this. Staff compared to Canadian carriers go above and beyond. Would gladly fly United again.

Comfortable seating POS to IAH. Food options were satisfactory. Good seat from IAH to ANC. Food options could be better.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

There could have been better food options in economy on the long 7hr trip from IAH to AM.

It was terribly delayed with zero support from united airlines. I reached at 1 am in the night. They did not provide any option to change the flights.

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

Pilot main message was to "be nice to her crew". Crew only instructed passenger to "move out of the aisles" rather than helping passengers place their luggage. Some passengers needed to exit early to make their connections yet cleaning crews rushed onboard to make their way past rushing outgoing passengers. AA needs better protocols and better customer service for the price paid for trips.

Delayed couple hours due to airplane maintenance issues, we boarded and then asked to unboard, but cmon!! Can they do the whole maintenance prior to boarding?

Boarding was horrendous! Took absolutely forever… and the delay from the broken coffee pot was really kind of ridiculous

The flight was over an hour delayed. The problem was they had the wrong aircraft at the gate, Joe in the world does that happen?

Delays and multiple changes in gates. In accurate info sent to phone. Worst flight in years. With no apologies or recompense.

No AC, no beverage service and no explanation from the captain. 4 flight legs in 2 days with no internet service.

The flight I booked was conveniently timed, had one brief stop and was going to be quick. The flight I ended up getting was delayed, took longer, had a far longer layover and arrived hours later than planned. Thanks for nothing.

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}.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports