$123 Find Cheap Flights from Houston to Caribbean Islands

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 9/15. 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 Cana1 stop$477
Santo Domingo
Santo Domingo1 stop$346
Montego Bay
Montego Bay1 stop$457
Oranjestad
Oranjestad1 stop$456
Nassau
Nassau1 stop$284
Kingston
Kingston1 stop$441
Simpson Bay
Simpson Bay1 stop$433
Providenciales
Providenciales1 stop$608
Port of Spain
Port of Spain1 stop$518
Bridgetown
Bridgetown1 stop$522
George Town
George Town1 stop$439
Willemstad
Willemstad2 stops$571
Aguadilla
Aguadilla1 stop$336
Puerto Plata
Puerto Plata2 stops$605
St. John's
St. John's1 stop$652
Punta Cana
Punta Cana1 stop$477
Santo Domingo
Santo Domingo1 stop$346
Montego Bay
Montego Bay1 stop$457
Oranjestad
Oranjestad1 stop$456
Nassau
Nassau1 stop$284
Kingston
Kingston1 stop$441
Simpson Bay
Simpson Bay1 stop$433
Providenciales
Providenciales1 stop$608
Port of Spain
Port of Spain1 stop$518
Bridgetown
Bridgetown1 stop$522
George Town
George Town1 stop$439
Willemstad
Willemstad2 stops$571
Aguadilla
Aguadilla1 stop$336
Puerto Plata
Puerto Plata2 stops$605
St. John's
St. John's1 stop$652

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

Wed, Jul 29 - Sat, Aug 22
Delta Logo
5:40 am - 3:20 pm
IAH
-
STT
8h 40m
1 stop
Delta Logo
2:49 pm - 11:52 pm
STT
-
IAH
10h 03m
1 stop
$250Delta
Tue, Sep 1 - Sat, Sep 5
JetBlue Logo
7:24 am - 5:14 pm
IAH
-
NAS
8h 50m
1 stop
JetBlue Logo
6:24 pm - 11:02 pm
NAS
-
IAH
5h 38m
1 stop
$284JetBlue
Tue, Aug 18 - Tue, Aug 25
Frontier Logo
8:29 am - 3:58 pm
IAH
-
SJU
30h 29m
1 stop
Frontier Logo
6:41 pm - 11:34 am
SJU
-
IAH
17h 53m
1 stop
$296Frontier
Tue, Aug 18 - Wed, Aug 26
Frontier Logo
8:29 am - 3:58 pm
IAH
-
SJU
30h 29m
1 stop
Frontier Logo
6:41 pm - 11:34 am
SJU
-
IAH
17h 53m
1 stop
$301Frontier
Tue, Aug 25 - Wed, Aug 26
Southwest Logo
6:25 am - 12:15 pm
HOU
-
NAS
4h 50m
1 stop
Southwest Logo
1:10 pm - 7:20 pm
NAS
-
HOU
7h 10m
1 stop
$330Southwest
Tue, Aug 25 - Wed, Aug 26
Southwest Logo
6:25 am - 12:15 pm
HOU
-
NAS
4h 50m
1 stop
Southwest Logo
1:10 pm - 8:05 pm
NAS
-
HOU
7h 55m
2 stops
$410Southwest
Sat, Oct 10 - Fri, Oct 16
Multiple Airlines Logo
7:00 am - 1:31 pm
IAH
-
MBJ
6h 31m
1 stop
Multiple Airlines Logo
3:10 pm - 11:02 pm
MBJ
-
IAH
7h 52m
1 stop
$458Multiple Airlines
Tue, Jul 28 - Mon, Aug 3
Multiple Airlines Logo
7:24 am - 4:42 pm
IAH
-
MBJ
9h 18m
1 stop
Multiple Airlines Logo
1:32 pm - 7:20 am
MBJ
-
IAH
17h 48m
1 stop
$464Multiple Airlines
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
5:41 am - 2:54 pm
HOU
-
SJU
8h 13m
1 stop
American Airlines Logo
3:44 pm - 8:59 am
SJU
-
HOU
18h 15m
1 stop
$471American Airlines
Sat, Sep 26 - Tue, Sep 29
American Airlines Logo
12:01 pm - 11:59 pm
HOU
-
SJU
10h 58m
2 stops
American Airlines Logo
6:30 am - 3:58 pm
SJU
-
HOU
10h 28m
2 stops
$476American Airlines
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 7 days was to Montego Bay, 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 7 days was $457.

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 in the afternoon, when round-trip flights cost $394 on average. Morning departures are around 11% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $539.

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 June, when tickets cost $675 (return) on average. On the other hand, the most expensive months are September and November, when the average cost of round-trip tickets is $1,190 and $1,056 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 Monday 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 5 weeks before departure.

Good to know

Cheapest flight$123
Flight from Houston Hobby Airport to Saint Thomas Island

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 4276 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

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!

We had excellent customer service despite the chaos at George Bush airport in Houston!

It isvvery small flight. No leg room . No space to put my personal item at feet.

Didn't make the flight because the first leg of my flight was canceled and the next leg was already booked.

Terrible because it was cancelled due to volcanic ash clouds in Guatemala while all other airlines kept flying. Had to pay for a hotel to stay overnight in Houston and try to fly next day.

Overall we had a good experience during our flight from San Francisco to Houston.

Cancelled BOYH legs of our flight home 30 min before initial boarding

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

The staff was nice. I appreciated that I was able to take an earlier flight, even though it was last minute. The boarding process felt rather chaotic.

My flight got delayed a total of five times. And the boarding gate changed four times. most of the time the platform was not up-to-date with the changes taking place. The most discouraging part of the entire trip by far.

Returned home with a blood clot from flight homes and the uncomfortable aircraft I was on.

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

Everything was delayed and the staff sent me to the wrong gate, causing me to miss one of my flights. I arrived at my destination 6 hours later than I was supposed to.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

It was really a terrific experience both going and returning on AA. Staff and crew were professional.

It would have been better IF IT HAD NOT BEEN CANCELED!!!!

Shut down without prior notice End up with spending lots of extra $$$

The company went out of business and now I'm stuck in Ft. Lauderdale. Would not recommend.

The repeated flight delays—this time nearly three hours without any weather-related cause—are unacceptable. Yet, passengers are penalized heavily even for being a minute late. It is unreasonable that there is no compensation for such significant delays, nor even basic provisions like water during the wait or in flight. This imbalance in accountability is deeply frustrating and needs to be addressed.

They didn’t put my luggage on my transfer so I had to spend the night in Detroit. They said my luggage would be here in the morning and they’re still searching for it. It did not arrive apparently.

Great just wish they always had WiFi on every flight couldn’t even purchase it

They keep delaying and cancel at last moment and height was for you to get refund need to be in chat line for two hours. I complained to DOT. Never recommend this airline on Kayak please

We had to take a bus to the plane with a old woman and carry on bags, and at landing at the airport we have to wait one hour seating on the plane waiting for a gate. We came back from Australia Bussines class Quantas 16 hours traveling, then wait in Dallas 7 hours for connection...honestly waiting 1 hour more at the plane was the worst part.

Flight delayed twice (not Spirit fault) No food served* No entertainment * *in response to my choices in the rating. None was provided so couldn’t rate properly

The flight was a big joke very uncomfortable I had a horrible experience and I will never fly with them again everything about the flight was bogus and I’m not happy with it at all this experience makes me not want to fly ever again

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.