Find cheap flights from Houston to Caribbean Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals
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 $407 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 $407.

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 $585 on average. Morning departures are around 5% 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 $620.

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

The cheapest month for flights from Houston to Caribbean Islands is February, when tickets cost $607 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $794 and $746 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 3 weeks before departure, which saves you about 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

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.
7.9
SouthwestOverall score based on 4209 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

It’s too cold like fridge and they don’t offer a blanket with expensive price

6.0 GoodJiana, Oct 2026
Read more Southwest reviews

It’s too cold like fridge and they don’t offer a blanket with expensive price

Horrible communication from Southwest. No accountability. Flight was delayed for 4 hours and TSA closed in the interim. We were not allowed to our gate. Southwest knew this information and did not relay to their customers to arrive to the airport earlier.

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.

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.

On time, quick boarding, so nice of them to honor active and retired military with early boarding. Attendants were nice . Plane was clean. A bit crowded like all flights.

Everything was great except the fact that catering did not restock the flight from ATL to GRB and we were only offered water.

The WiFi on the plane was out. I also thought movie options were lacking.

These Delta 717 jets are ancient. No entertainment and you have to pay for WiFi that barely works and goes in and out the whole flight. Delta should be ashamed flying this garbage.

My seat was changed without my consent. It wasn’t a major deal but annoying.

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

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.

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. ❤️

- delayed because video screens not working - delayed getting a gate at DCA Just continued bad experience IAH to DCA.

I couldn’t give an honest evaluation, because the Houston airport has a problem and I was stand up for several hours and after a long trip from Munich I feel really very tired

The experience was good overall; however, my United Airlines Mileage Plus Account didn't reflect my flights to Houston from Newark. In essence, my mileage rewards points do not reflect my actual travel. This should be corrected.

Good flight, even though there was a delay, still got back on time

First class flight crew was barely available. They came through 3 times while we were on the plane for nearly 4 hours.

It was partially ok .. not anything like from Orlando to Houston... first the flight attendant was not so nice and insisted on have a small backpack down when really was not to put in danger anyone, also the beverages they were not so good... not big chance to select other tea.. the seat was partially ok could not have those flips to hold your head.. and finally when it land off in Guadalajara, it was raining and the flight was going to the main area then go back and drop us out of nowhere with the rain.

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.

I am always very pleased with the service u receive from JetBlue employees

Your Jet Blue representative at the check in desk in Boston on Sunday morning, October 13, was unkind and unhelpful. For that reason alone I will avoid JetBlue airlines in the future. No food or beverage on the flight due to turbulence (not your fault). However I paid extra to sit in the upgraded section in the front and did not benefit from most amenities.

we used to fly with a different airline but it shut down. We had to find an alternative airline that we like in order to make domestic trips and this fits the bill. Not only is it a similar price but the customer service and the experience overall is much much better. We will be using JetBlue again.

Uncomfortable seat. No help for my disability. Staff refused to help me put my carry-on in the overhead bin. So I had to check the bag.

Terrible. Quality has gone down significantly. Plane was delayed. No instructions from the staff. Will try to avoid in the future!

The flight left unexpectedly early. Although I checked in at the gate, the crew made no attempt to contact me to inform me that what had been a delayed flight was now departing before the scheduled departure time. No announcement on the PA, no phone call. When I checked back at the gate for the delay status just before the scheduled departure time, I was told the doors were already locked and the flight had left.

Late boarding, had to check the bag even though there was space on the flight and I was I row 7

Our seats were moved for no reason. The plane was old and wifi and tv were slow. The flight was delayed over an hour for a paperwork issue. Only bright spot was the flight attendants good service.

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!

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.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental