$87 Find Cheap Flights from Houston 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 Houston to Caribbean Islands departing on 2/21. 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 Houston to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Caribbean Islands.
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Cheap Flights from Houston to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$299
Santo Domingo
Santo Domingo1 stop$256
Montego Bay
Montego Bay1 stop$255
Oranjestad
Oranjestad1 stop$277
Nassau
Nassau1 stop$381
Kingston
Kingston1 stop$410
Simpson Bay
Simpson Bay1 stop$233
Providenciales
Providenciales1 stop$267
Port of Spain
Port of Spain1 stop$433
Bridgetown
Bridgetown1 stop$642
George Town
George Town1 stop$257
Willemstad
Willemstad2 stops$490
St. John's
St. John's1 stop$620
Puerto Plata
Puerto Plata1 stop$549
Aguadilla
Aguadilla1 stop$178
Punta Cana
Punta Cana1 stop$299
Santo Domingo
Santo Domingo1 stop$256
Montego Bay
Montego Bay1 stop$255
Oranjestad
Oranjestad1 stop$277
Nassau
Nassau1 stop$381
Kingston
Kingston1 stop$410
Simpson Bay
Simpson Bay1 stop$233
Providenciales
Providenciales1 stop$267
Port of Spain
Port of Spain1 stop$433
Bridgetown
Bridgetown1 stop$642
George Town
George Town1 stop$257
Willemstad
Willemstad2 stops$490
St. John's
St. John's1 stop$620
Puerto Plata
Puerto Plata1 stop$549
Aguadilla
Aguadilla1 stop$178

Book Cheap Houston 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 Houston 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 Houston to Caribbean Islands

Sat, Feb 28 - Tue, Mar 3
Multiple Airlines Logo
8:18 pm - 2:53 am
IAH
-
SJU
28h 35m
1 stop
Multiple Airlines Logo
11:52 am - 11:59 pm
SJU
-
IAH
14h 07m
1 stop
$185Multiple Airlines
Fri, Feb 6 - Thu, Feb 12
Multiple Airlines Logo
8:35 pm - 9:47 am
IAH
-
SJU
11h 12m
1 stop
Multiple Airlines Logo
4:11 pm - 10:51 pm
SJU
-
IAH
8h 40m
1 stop
$186Multiple Airlines
Sun, Feb 1 - Sat, Feb 14
Spirit Airlines Logo
8:35 pm - 9:47 am
IAH
-
SJU
11h 12m
1 stop
Spirit Airlines Logo
4:36 pm - 12:18 am
SJU
-
IAH
9h 42m
1 stop
$187Spirit Airlines
Wed, Mar 11 - Tue, Mar 17
Spirit Airlines Logo
9:16 am - 4:32 pm
IAH
-
SJU
6h 16m
1 stop
Spirit Airlines Logo
11:07 am - 11:49 pm
SJU
-
IAH
13h 42m
1 stop
$188Spirit Airlines
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
1:35 pm - 12:35 am
HOU
-
SJU
9h 00m
2 stops
Southwest Logo
5:40 am - 12:50 pm
SJU
-
HOU
9h 10m
2 stops
$364Southwest
Wed, Mar 4 - Tue, Mar 10
Southwest Logo
11:15 am - 11:10 pm
HOU
-
SJU
9h 55m
2 stops
Southwest Logo
5:55 am - 1:40 pm
SJU
-
HOU
8h 45m
2 stops
$382Southwest
Mon, Mar 9 - Wed, Mar 11
American Airlines Logo
6:00 am - 2:04 pm
HOU
-
MBJ
8h 04m
1 stop
American Airlines Logo
3:04 pm - 11:58 pm
MBJ
-
HOU
8h 54m
1 stop
$438American Airlines
Wed, Mar 25 - Tue, Mar 31
Delta Logo
6:00 am - 3:28 pm
HOU
-
MBJ
9h 28m
1 stop
Delta Logo
11:15 am - 10:42 pm
MBJ
-
HOU
11h 27m
1 stop
$440Delta
Mon, Feb 23 - Thu, Mar 5
Delta Logo
5:25 am - 2:25 pm
HOU
-
PUJ
7h 00m
1 stop
Delta Logo
4:55 pm - 10:28 pm
PUJ
-
HOU
7h 33m
1 stop
$443Delta
Fri, Feb 20 - Mon, Feb 23
American Airlines Logo
6:00 am - 2:53 pm
HOU
-
MBJ
7h 53m
1 stop
American Airlines Logo
3:53 pm - 11:48 am
MBJ
-
HOU
20h 55m
1 stop
$447American Airlines
Booking Insights

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

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

What is the cheapest Houston to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Houston found in the last 72 hours was to San Juan, at $371 round-trip. The most popular route is from Houston George Bush Intcntl Airport (IAH) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $371.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Houston 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 Houston to Caribbean Islands is April, when tickets cost $282 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $490 and $432 respectively.

What’s the cheapest day of the week to fly from Houston to Caribbean Islands?

The average price of all round-trip flights from Houston to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

For Houston to Caribbean Islands, Sunday is the cheapest day to fly on average and Friday is the most expensive. Flying from Caribbean Islands back to Houston, the best deals are generally found on Thursday, with Sunday being the most expensive.

How far in advance should I book a flight from Houston to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Houston to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Houston to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Cheapest flight$87
Flight from Houston George Bush Airport to San Juan

Flights from Houston to Caribbean Islands: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Houston to Caribbean Islands 
JoseFlew with United Airlines
IAH
-
SJU
Sep 2024
Eat before your boarding. Buy snacks or anything you like before departure, also download a movie, music or an audio book to enjoy during your flight.
KerryFlew with United Airlines
IAH
-
POS
Dec 2023
There was no internet and it seems like there never is. Charge your devices and pre-download your movies or audio.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Houston 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 Houston to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Houston 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 Houston 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 Houston 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 Houston 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 Houston to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $253 on average. Morning departures are around 17% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $486.

Reviews of the top 5 airlines serving from Houston to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Houston 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 Houston 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.
8.0
SouthwestOverall score based on 4268 reviews
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

I like flying first class, and United has a nice one

Unbelievably poor service from flight attendants. They didn’t even do water service on a four hour flight. Just disrespectful.

Seats had less pitch than a regional jet. Food was OK. Have to buy alcohol on US based carriers flying international. Boarding was a mess. Did not have bags but overhead space was gone quick. Would like to see the airlines enforce the one bag over and one bag under policy

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Crew was excellent. This was a relatively long flight though and had very little leg room, and no entertainment.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Plane was crowded and even when we hit altitude, the plane was hot, not enough air flow.

Flight was delayed and missed my connection Lufthansa didn’t respond.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

The seat cushions were very worn so they were extremely uncomfortable.

Delayed, no updates, had a rewards number but was not working

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The professionals have excellent customer service, the seats don´t have enough space.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

Seats were much more cramped then on the 737. Narrower and rows closer together. Flight was absolutely packed and the plugs under the seats didn't work. Was forced to check my bag even though previous flight had no issue with it.

Good food & refreshment. The seats and entrainment screens are modern compared to others. The staff though pleasant serve and attend to passengers based on nationality. Some get served first others last regardless of their seating positions.

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Sadly there was a crew member very rude with my kid and with me.

They canceled the flight and didn't assist in getting a new flight on any airline. I had to spend 10 hrs in the airport after getting a ticket On Delta for twice as much. I've flown Spirit many times and this was my worst experience I've had.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

We had too many delays for the crew not the plane

Awful!!! Spirit cancelled my flight just 4 hours before departure- with no alternative flights available. I ended up missing a huge family gathering because I wasn’t able to get out. Such An awful experience. And on top of that, all the buckle and dime-ing for bags. I will never book with Spirit EVER

I'd have like to check my bag and not toss my hair products.sears are very uncomfortable. And that even water isn't free really sucks. The ticket was almost $400

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

Flight was canceled and instead of rescheduling at the gate we had to go out to the ticket counter. Unruly kids kicking the back of my rows chair with staff to inattentive to say something.

Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Houston

Cabin classes available on flights to Houston. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.