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Cheap Flights from Houston to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stops$528
Santo Domingo
Santo Domingo1 stop$409
Montego Bay
Montego Bay1 stop$415
Oranjestad
Oranjestad1 stop$417
Nassau
Nassau1 stop$405
Kingston
Kingston1 stop$540
Providenciales
Providenciales1 stop$426
Aguadilla
Aguadilla1 stop$296
Puerto Plata
Puerto Plata2 stops$606
Punta Cana
Punta Cana2 stops$528
Santo Domingo
Santo Domingo1 stop$409
Montego Bay
Montego Bay1 stop$415
Oranjestad
Oranjestad1 stop$417
Nassau
Nassau1 stop$405
Kingston
Kingston1 stop$540
Providenciales
Providenciales1 stop$426
Aguadilla
Aguadilla1 stop$296
Puerto Plata
Puerto Plata2 stops$606
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?

The cheapest ticket to Caribbean Islands from Houston found in the last 5 days was to San Juan, at $344 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 $344.

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

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $583 on average. Morning departures are around 1% more expensive than evening flights, on average. 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?

The cheapest month for flights from Houston to Caribbean Islands is January, when tickets cost $598 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $755 and $742 respectively.

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

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 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 6 weeks before departure.

Good to know

Cheapest flight

$95
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

 
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 4199 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
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.

Everything went smooth from check in, thru TSA, then boarding, and a smooth flight to ATL.

I had an extensive delay on my previous flight and we had another delay due to the crew not being there. We were scheduled to have a late arrival but due to the delay it was even longer.

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.

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. ❤️

Really old place. Not as clean as it should be, tray tables needed better cleaning. The items, trays and some other items need to b6 engineered. Anything task you or crew may do is incredibly load, seriously engineer for quiet smooth, easy. Just opening and closing the tray table is actually dangerous and can easily injure a finger. I'm sure it happens as it happened to me! First time I used United and likely will be the last!

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.

Platinum status. 65 people in the upgrades list. When everyone is special No one is

Great for a small Commuter. Quiet and relaxing. Seats were better than most.

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.

Poor, had a 5+ hours delay. Kept sitting in the aircraft with three kids. It was terrible

The plane was filthy and worn - the seat pockets were stuffed with tattered food and torn pamphlets. The cleaning crew that came on as we were deboarding were grabbing handfulls of trash and perfunctorily wiping down tables with dishrags. It's been a while since I flew Jetblue and it used to be a great experience. After this flight I will avoid flying Jetblue again if there is any alternative.

I have flown Jet Blue many times between JFK and SFO. I appreciate how clean the planes are, the ability to select my onboard entertainment and the flight crews have always been amazing! Unfortunately, my trip from SFO to JFK on August 23 was unusual. I arrived early at SFO for the 12:00 noon scheduled boarding. The flight was supposed to take off at 12:45pm but after sitting for a while, the plane had to return to the gate to have a generator inspected. After deplaning and then reboarding, we eventually took off around 3:30 pm. It was explained to the passengers that because the plane was using a backup generator, additional fuel was needed and the flight would take longer than originally scheduled. We were originally supposed to arrive at JFK at 9:32 pm but instead, arrived at midnight. Unfortunately, I was exhausted for the funeral I attended the next morning. As a passenger, I have always expected that the plane will be in good mechanical order and that all parts will function as expected. I'm not entirely certain that if I fly Jet Blue in the future, that I will have the same level of confidence that I had become accustomed to. Thanks for the opportunity to provide this feedback. Kathy Nigro

The series of delays were very unfortunately - first the captain timed out, then the new captain didn't show up when we were told he would, then the first officer timed out. Those delays were compounded by after boarding, weather came in - obviously that's out of JB's control but it was frustrating after all of the other delays that seemed avoidable.

3 hours late JetBlue flight made me miss my connecting flight to Nairobi Kenya, they did not even offer me hotel accommodation, I paid out of my pocket, they did not know where my luggage was, let say my experience with JetBlue was nightmare.

JFK is the worst airport and JetBlue is the worst airline

Crew at first tried to SELL snack boxes (for an hour-long flight?!?), and it was the only leg of four on which I was charged for a hard seltzer. 😕 Spent extra to select seats in Row 8 for quicker disembarking only to be seated in Row 25. Someone owes me $38 for that!

My screen didn’t work, my seat didn’t recline, the flight attendant was rude and completely dismissive, the airplane was freezing, the seats are way old, slanted and uncomfortable. I payed for a full ticket and got a horrific experience, with a flight attendant who dismissed me even though I was calm respectful and polite.

The wifi didn't work and I needed to do some work. This was a business trip.

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