$107 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 7/11. 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 Cana2 stops$499
Santo Domingo
Santo Domingo1 stop$380
Montego Bay
Montego Bay1 stop$461
Oranjestad
Oranjestad1 stop$396
Nassau
Nassau1 stop$322
Kingston
Kingston1 stop$418
Simpson Bay
Simpson Bay1 stop$325
Providenciales
Providenciales1 stop$554
Port of Spain
Port of Spain1 stop$478
Bridgetown
Bridgetown1 stop$563
George Town
George Town1 stop$413
Willemstad
Willemstad2 stops$569
Aguadilla
Aguadilla1 stop$296
Puerto Plata
Puerto Plata1 stop$625
St. John's
St. John's1 stop$670
Punta Cana
Punta Cana2 stops$499
Santo Domingo
Santo Domingo1 stop$380
Montego Bay
Montego Bay1 stop$461
Oranjestad
Oranjestad1 stop$396
Nassau
Nassau1 stop$322
Kingston
Kingston1 stop$418
Simpson Bay
Simpson Bay1 stop$325
Providenciales
Providenciales1 stop$554
Port of Spain
Port of Spain1 stop$478
Bridgetown
Bridgetown1 stop$563
George Town
George Town1 stop$413
Willemstad
Willemstad2 stops$569
Aguadilla
Aguadilla1 stop$296
Puerto Plata
Puerto Plata1 stop$625
St. John's
St. John's1 stop$670

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, Aug 29 - Wed, Sep 2
JetBlue Logo
7:24 am - 5:22 pm
IAH
-
NAS
8h 58m
1 stop
JetBlue Logo
10:42 am - 3:47 pm
NAS
-
IAH
6h 05m
1 stop
$322JetBlue
Sun, Sep 13 - Thu, Sep 17
JetBlue Logo
6:35 am - 4:00 pm
IAH
-
NAS
8h 25m
1 stop
JetBlue Logo
5:57 pm - 10:07 pm
NAS
-
IAH
5h 10m
1 stop
$329JetBlue
Wed, Jul 22 - Wed, Jul 29
Frontier Logo
9:09 am - 12:23 am
IAH
-
SJU
14h 14m
1 stop
Frontier Logo
6:00 am - 2:50 pm
SJU
-
IAH
9h 50m
1 stop
$359Frontier
Wed, Jul 22 - Fri, Jul 31
Frontier Logo
10:53 am - 1:55 pm
IAH
-
SJU
26h 02m
2 stops
Frontier Logo
7:30 am - 8:24 am
SJU
-
IAH
25h 54m
1 stop
$362Frontier
Wed, Aug 12 - Wed, Aug 19
Southwest Logo
8:00 am - 10:00 pm
HOU
-
SJU
13h 00m
1 stop
Southwest Logo
5:15 am - 1:50 pm
SJU
-
HOU
9h 35m
2 stops
$376Southwest
Sun, Aug 30 - Wed, Sep 2
Southwest Logo
5:00 am - 12:15 pm
HOU
-
NAS
6h 15m
1 stop
Southwest Logo
1:10 pm - 7:20 pm
NAS
-
HOU
7h 10m
1 stop
$390Southwest
Wed, Sep 23 - Sun, Sep 27
American Airlines Logo
6:04 am - 8:47 pm
HOU
-
SJU
13h 43m
2 stops
American Airlines Logo
4:19 pm - 8:56 am
SJU
-
HOU
17h 37m
1 stop
$431American Airlines
Thu, Sep 24 - Sun, Sep 27
American Airlines Logo
8:18 pm - 2:45 pm
HOU
-
SJU
17h 27m
1 stop
American Airlines Logo
4:19 pm - 8:56 am
SJU
-
HOU
17h 37m
1 stop
$438American Airlines
Wed, Oct 14 - Wed, Oct 21
Delta Logo
6:00 am - 1:20 pm
HOU
-
MBJ
7h 20m
1 stop
Delta Logo
1:32 pm - 9:43 pm
MBJ
-
HOU
8h 11m
1 stop
$502Delta
Sun, Sep 13 - Thu, Sep 17
Delta Logo
6:00 am - 1:25 pm
HOU
-
PUJ
6h 25m
1 stop
Delta Logo
4:00 pm - 10:40 pm
PUJ
-
HOU
7h 40m
1 stop
$550Delta
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 Montego Bay, at $485 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 $523.

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 $558 on average. Morning departures are around 2% 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?

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 May, when tickets cost $674 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $1,019 and $1,008 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$107
Flight from Houston George Bush Airport to Nassau

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.

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.
7.9
SouthwestOverall score based on 4246 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

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.

2.0 MediocreMarcela, Jun 2026
DAL - COS
Read more Southwest reviews

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.

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.

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

We departed and landed early which was a nice surprise. The boarding process was slow.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

The WiFi was not working. That made for a long flight.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Flight was delayed due to crew being not on time

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. ❤️

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.

Boarded early, left early, arrived 40 mins early! A win win for me!

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

We had a delay, but thankfully I made it to my connection. Overall it went smooth

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

It's a long flight and I would have liked better snacks between lunch and the arrival meal. It's fine to have fruit and nuts but I really don't like ramen because it's salty junk soup. I'd suggest sandwiches. They're not expensive nor are they hard to store for a long flight. The FA's had a couple of big services and they were super busy preparing, executing and then cleaning up. Then they disappeared.

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

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.

Left 40 mins late; we were fine on our connection but many on our flight were not.

Pros: "The crew member who is close to my seat did not even offer to help with my luggage which was very unprofessional."
Cons: "The crew members needs to be helpful, and customer service to their passengers!"

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

Domestic flights are good. Just stay away from international travel

Flight left 2 hours late with no explanation as to the delay

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

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.