$99 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 9/12. 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$498
Santo Domingo
Santo Domingo1 stop$436
Montego Bay
Montego Bay2 stops$513
Oranjestad
Oranjestad2 stops$478
Nassau
Nassau1 stop$408
Kingston
Kingston1 stop$458
Simpson Bay
Simpson Bay2 stops$441
Providenciales
Providenciales1 stop$519
Port of Spain
Port of Spain2 stops$468
Bridgetown
Bridgetown1 stop$475
George Town
George Town1 stop$398
Willemstad
Willemstad2 stops$571
Aguadilla
Aguadilla1 stop$310
St. John's
St. John's1 stop$620
Puerto Plata
Puerto Plata1 stop$630
Punta Cana
Punta Cana2 stops$498
Santo Domingo
Santo Domingo1 stop$436
Montego Bay
Montego Bay2 stops$513
Oranjestad
Oranjestad2 stops$478
Nassau
Nassau1 stop$408
Kingston
Kingston1 stop$458
Simpson Bay
Simpson Bay2 stops$441
Providenciales
Providenciales1 stop$519
Port of Spain
Port of Spain2 stops$468
Bridgetown
Bridgetown1 stop$475
George Town
George Town1 stop$398
Willemstad
Willemstad2 stops$571
Aguadilla
Aguadilla1 stop$310
St. John's
St. John's1 stop$620
Puerto Plata
Puerto Plata1 stop$630

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

Fri, Aug 21 - Sun, Aug 23
Frontier Logo
3:25 pm - 2:15 am
IAH
-
SJU
9h 50m
1 stop
Frontier Logo
7:30 am - 8:44 am
SJU
-
IAH
26h 14m
1 stop
$362Frontier
Mon, Oct 12 - Sat, Oct 17
JetBlue Logo
4:42 pm - 9:02 am
IAH
-
SJU
15h 20m
1 stop
JetBlue Logo
9:00 am - 11:02 pm
SJU
-
IAH
15h 02m
1 stop
$364JetBlue
Thu, Nov 5 - Thu, Nov 12
Multiple Airlines Logo
8:36 am - 12:38 am
IAH
-
SJU
14h 02m
1 stop
Multiple Airlines Logo
6:25 am - 3:47 pm
SJU
-
IAH
11h 22m
1 stop
$364Multiple Airlines
Thu, Nov 5 - Wed, Nov 11
Multiple Airlines Logo
8:36 am - 12:38 am
IAH
-
SJU
14h 02m
1 stop
Multiple Airlines Logo
5:10 pm - 11:02 pm
SJU
-
IAH
7h 52m
1 stop
$364Multiple Airlines
Sat, Aug 8 - Sun, Aug 23
Frontier Logo
8:37 pm - 12:28 am
IAH
-
SJU
26h 51m
1 stop
Frontier Logo
6:35 am - 7:20 am
SJU
-
IAH
25h 45m
2 stops
$364Frontier
Fri, Sep 11 - Mon, Sep 14
United Airlines Logo
3:06 pm - 8:38 pm
IAH
-
SJU
4h 32mnonstop
United Airlines Logo
7:00 am - 10:45 am
SJU
-
IAH
4h 45mnonstop
$367United Airlines
Sat, Sep 12 - Sun, Sep 20
United Airlines Logo
10:10 am - 3:42 pm
IAH
-
SJU
4h 32mnonstop
United Airlines Logo
7:00 am - 10:45 am
SJU
-
IAH
4h 45mnonstop
$367United Airlines
Wed, Nov 18 - Wed, Dec 2
JetBlue Logo
1:00 pm - 11:04 pm
IAH
-
SJU
8h 04m
1 stop
JetBlue Logo
6:10 pm - 10:53 pm
SJU
-
IAH
6h 43m
1 stop
$367JetBlue
Sun, Sep 20 - Fri, Sep 25
Delta Logo
6:00 am - 4:49 pm
HOU
-
SJU
9h 49m
1 stop
Delta Logo
2:59 pm - 10:39 pm
SJU
-
HOU
8h 40m
1 stop
$376Delta
Sat, Sep 26 - Tue, Sep 29
Delta Logo
11:08 am - 10:19 pm
HOU
-
SJU
10h 11m
1 stop
Delta Logo
2:59 pm - 10:39 pm
SJU
-
HOU
8h 40m
1 stop
$381Delta
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 $369 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 $369.

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 $579 on average. Morning departures are around 1% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $588.

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 $554 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $745 and $742 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 6 weeks before departure.

Good to know

Cheapest flight

$99
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.

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 4227 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

8.0 ExcellentSean, Jul 2026
HOU - LGB
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.

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

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.

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. ❤️

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.

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

Horrible. No AC. No Air inside the plane. We had to deplane twice! It is late almost 5 hrs in total. I almost passed out and about to call 911. I asked the crew to be honest and open the door. The lady next to me was lay down in the floor due to heat and no air inside the plane. I got headaches, can’t wait the replacement flight about midnight Dallas time. I end it up rebook for next day flight and stay overnight using my own pocket in a hotel nearby due to headaches and can’t breath. I still have a headache this morning. Still not decided yes how to file this issue to AA and/or FAA.

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.

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.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

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.