$90 Find Cheap Flights from Houston 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 Houston to Caribbean Islands departing on 10/6. 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.
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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 Cana2 stops$520
Santo Domingo
Santo Domingo1 stop$431
Montego Bay
Montego Bay1 stop$398
Oranjestad
Oranjestad1 stop$455
Nassau
Nassau1 stop$383
Kingston
Kingston1 stop$546
Simpson Bay
Simpson Bay1 stop$403
Providenciales
Providenciales1 stop$410
Port of Spain
Port of Spain1 stop$465
Bridgetown
Bridgetown1 stop$460
George Town
George Town1 stop$406
Willemstad
Willemstad1 stop$441
Aguadilla
Aguadilla1 stop$316
St. John's
St. John's1 stop$665
Puerto Plata
Puerto Plata2 stops$615
Punta Cana
Punta Cana2 stops$520
Santo Domingo
Santo Domingo1 stop$431
Montego Bay
Montego Bay1 stop$398
Oranjestad
Oranjestad1 stop$455
Nassau
Nassau1 stop$383
Kingston
Kingston1 stop$546
Simpson Bay
Simpson Bay1 stop$403
Providenciales
Providenciales1 stop$410
Port of Spain
Port of Spain1 stop$465
Bridgetown
Bridgetown1 stop$460
George Town
George Town1 stop$406
Willemstad
Willemstad1 stop$441
Aguadilla
Aguadilla1 stop$316
St. John's
St. John's1 stop$665
Puerto Plata
Puerto Plata2 stops$615

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

Thu, Sep 10 - Sun, Sep 13
Frontier Logo
2:18 pm - 2:13 amIAH  Houston George Bush Intcntl-SJU San Juan Luis Munoz Marin Intl
10h 55m1 stop Miami
Frontier Logo
7:50 am - 7:17 amSJU  San Juan Luis Munoz Marin Intl-IAH Houston George Bush Intcntl
24h 27m2 stops Jacksonville Atlanta Hartsfield-Jackson
$324Frontier
Sun, Aug 23 - Thu, Aug 27
Frontier Logo
8:11 pm - 12:43 amIAH  Houston George Bush Intcntl-SJU San Juan Luis Munoz Marin Intl
27h 32m1 stop Miami
Frontier Logo
7:30 am - 8:44 amSJU  San Juan Luis Munoz Marin Intl-IAH Houston George Bush Intcntl
26h 14m1 stop Miami
$325Frontier
Mon, Oct 12 - Sat, Oct 17
JetBlue Logo
4:42 pm - 9:02 amIAH  Houston George Bush Intcntl-SJU San Juan Luis Munoz Marin Intl
15h 20m1 stop Fort Lauderdale
JetBlue Logo
9:00 am - 11:02 pmSJU  San Juan Luis Munoz Marin Intl-IAH Houston George Bush Intcntl
15h 02m1 stop Fort Lauderdale
$329JetBlue
Mon, Oct 12 - Sat, Oct 17
JetBlue Logo
4:42 pm - 9:02 amIAH  Houston George Bush Intcntl-SJU San Juan Luis Munoz Marin Intl
15h 20m1 stop Fort Lauderdale
JetBlue Logo
6:25 am - 11:47 amSJU  San Juan Luis Munoz Marin Intl-IAH Houston George Bush Intcntl
6h 22m1 stop Fort Lauderdale
$331JetBlue
Fri, Sep 11 - Tue, Sep 15
Multiple Airlines Logo
6:15 am - 3:23 pmIAH  Houston George Bush Intcntl-SJU San Juan Luis Munoz Marin Intl
8h 08m1 stop Fort Lauderdale
Multiple Airlines Logo
10:42 am - 9:14 pmSJU  San Juan Luis Munoz Marin Intl-IAH Houston George Bush Intcntl
11h 32m1 stop Orlando
$336Multiple Airlines
Sat, Sep 5 - Tue, Sep 8
Multiple Airlines Logo
1:00 pm - 8:27 pmIAH  Houston George Bush Intcntl-SJU San Juan Luis Munoz Marin Intl
6h 27m1 stop Fort Lauderdale
Multiple Airlines Logo
7:14 pm - 10:30 amSJU  San Juan Luis Munoz Marin Intl-IAH Houston George Bush Intcntl
16h 16m1 stop Chicago O'Hare Intl
$336Multiple Airlines
Mon, Sep 7 - Thu, Sep 10
American Airlines Logo
7:15 am - 1:36 pmIAH  Houston George Bush Intcntl-NAS Nassau Intl
5h 21m1 stop Miami
American Airlines Logo
12:34 pm - 5:17 pmNAS  Nassau Intl-IAH Houston George Bush Intcntl
5h 43m1 stop Miami
$396American Airlines
Thu, Nov 5 - Mon, Nov 9
American Airlines Logo
6:28 pm - 9:30 amIAH  Houston George Bush Intcntl-NAS Nassau Intl
14h 02m1 stop Miami
American Airlines Logo
6:45 pm - 11:58 pmNAS  Nassau Intl-IAH Houston George Bush Intcntl
6h 13m1 stop Miami
$396American Airlines
Sun, Oct 25 - Wed, Nov 4
Delta Logo
6:09 am - 3:29 pmHOU  Houston Hobby-MBJ Montego Bay Sangster Intl
9h 20m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:26 pm - 11:03 pmMBJ  Montego Bay Sangster Intl-HOU Houston Hobby
8h 37m1 stop Atlanta Hartsfield-Jackson
$450Delta
Sun, Oct 25 - Thu, Nov 5
Delta Logo
6:09 am - 11:51 amHOU  Houston Hobby-MBJ Montego Bay Sangster Intl
5h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:16 pm - 11:03 pmMBJ  Montego Bay Sangster Intl-HOU Houston Hobby
9h 47m1 stop Atlanta Hartsfield-Jackson
$450Delta
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 5 days was to San Juan, at $367 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 5 days was $367.

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

The average price for all round-trip flights from Houston to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $582 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $587.

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 October, when tickets cost $576 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $743 and $743 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, Tuesday 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 7 weeks before departure.

Good to know

Cheapest flight

$90
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-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-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.

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 4216 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
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 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.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

My experience was find with Southwest. The only issue I have is...at the exact time for me to check in...I don't understand how I always end up in C.

Very helpful, convenient, nice crew members, no extra fees, helped us saving 4 hrs of travel by booking is on an earlier flight

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

It was a very good experience. No major issues at all.

overall the crew onboarding and providing service during our flight was great; they were friendly and helpful. I said ok to the entertainment because there was none, but the crew explained why which was very helpful. I am a diabetic and the type of snacks are not diabetic friendly (full of carbs and sugar). However, I am always prepared because I know the catering is for the larger population.

No tv. No free wifi. They need to ipgrade these planes - especially on a 2 hour flight.

delta wifi wouldn’t work boarding was not in sequence flight crew spent most of their time on the phone with the lights off pretending no one wanted or needed anything

Flight was 2 hr. delay, making me miss my connection to my final flight home to Roanoke. Now 12:38am in the morning and I just got the first available ticket at 5:30 pm tomorrow evening. Sleeping in the airport.

I am a die hard Delta flyer, but they missed it on this flight. It was on their very dated 717-200 aircraft, which I knew when I booked it so I knew it wouldn’t have seatback screens. However, the internet was awful and it wouldn’t even send texts a lot of the time, much less even connect to the delta app. It was also very hot while in the air, which never happens. What was even more disappointing is that the crew only gave me cheezits and a beverage, even though I was in Delta Comfort. The main cabin fare gets these items. I didn’t get any kind of improved snacks and that was unacceptable. The crew wasn’t very visible at all either. If this was my first delta flight, it would be my last. I am just going to assume it was a one-off flight.

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

bulkhead seat had very little legroom - even in bsiness class.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

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.

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

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

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.

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

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

They changed my seat from one that I had paid for as an upgrade to a regular seat at the last minute.

Very aggressive and unhelpful ground crew. Wanted to check my hand luggage for 3 flights. I had lots of delicate items and computer equipment. So the silly lady wanted to rebook 3 international flights because of a carry on. What nonsense. The baggage handler suggested I put it under my seat - so I did. And this was during the rebooking chaos of the Microsoft crash. She was the most arrogant annoying and aggressive ground staff member I’ve met in 20yrs. (AA flight out of Houston).

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

Was as expected. Good leg room on planes - much appreciated.

I know that there is nothing than can be done about rude customers. I did find a couple of them were very rude and inconsiderate In my case the guy who was sitting in the same row as I was in, was trying to watch a movie with no headphones, a crew member did ask him to turn it down or off (thumbs up for that.) Another thing, as we were about to land another young man must have taken his phone off airplane mode was talking with his friends and using fowl language which I found inappropriate to the ppl who were sitting in the same row as him and other ppl around him. I understand how no one wanted to address this person and not get involved. We all just wanted to get home safely with out any incident.

The food service was limited and not good. For a seven hour flight they could do better.

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

The flight was on time the crew was courteous that makes for a good flight.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

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.