$55 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 5/6. 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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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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Best Caribbean Islands Flight Deals from Houston

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$246
Santo Domingo
Santo Domingo1 stop$310
Montego Bay
Montego Bay1 stop$298
Oranjestad
Oranjestad1 stop$308
Nassau
Nassau1 stop$416
Kingston
Kingston1 stop$327
Simpson Bay
Simpson Bay1 stop$348
Providenciales
Providenciales2 stops$570
Bridgetown
Bridgetown1 stop$621
Port of Spain
Port of Spain1 stop$463
George Town
George Town1 stop$453
Willemstad
Willemstad2 stops$553
St. John's
St. John's2 stops$424
Puerto Plata
Puerto Plata2 stops$519
Aguadilla
Aguadilla1 stop$368
Punta Cana
Punta Cana1 stop$246
Santo Domingo
Santo Domingo1 stop$310
Montego Bay
Montego Bay1 stop$298
Oranjestad
Oranjestad1 stop$308
Nassau
Nassau1 stop$416
Kingston
Kingston1 stop$327
Simpson Bay
Simpson Bay1 stop$348
Providenciales
Providenciales2 stops$570
Bridgetown
Bridgetown1 stop$621
Port of Spain
Port of Spain1 stop$463
George Town
George Town1 stop$453
Willemstad
Willemstad2 stops$553
St. John's
St. John's2 stops$424
Puerto Plata
Puerto Plata2 stops$519
Aguadilla
Aguadilla1 stop$368

Cheap Flight Deals from Houston to Caribbean Islands

 
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.

Recent round-trip flight deals from Houston to Caribbean Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Houston to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
United Airlines Logo
10:02 am - 3:40 pmIAH-SJU
4h 38mnonstop
United Airlines Logo
1:05 am - 10:50 amSJU-IAH
10h 45m1 stop
$145United Airlines
Find Deal
Tue, May 13 - Tue, May 13
United Airlines Logo
3:02 pm - 8:38 pmIAH-SJU
4h 36mnonstop
United Airlines Logo
1:25 pm - 11:47 pmSJU-IAH
11h 22m1 stop
$151United Airlines
Find Deal
Tue, May 13 - Wed, May 14
Spirit Airlines Logo
4:55 pm - 10:17 pmIAH-SJU
4h 22mnonstop
Spirit Airlines Logo
8:12 pm - 7:53 amSJU-IAH
12h 41m1 stop
$157Spirit Airlines
Find Deal
Sun, May 11 - Sat, May 17
Spirit Airlines Logo
6:50 am - 12:54 amIAH-SJU
17h 04m1 stop
Spirit Airlines Logo
11:50 am - 3:50 pmSJU-IAH
5h 00mnonstop
$167Spirit Airlines
Find Deal
Thu, May 15 - Thu, May 29
American Airlines Logo
8:52 am - 8:09 pmIAH-SJU
10h 17m2 stops
American Airlines Logo
6:10 am - 4:03 pmSJU-IAH
10h 53m1 stop
$215American Airlines
Find Deal
Tue, May 13 - Wed, May 14
Delta Logo
6:00 am - 4:50 pmHOU-SJU
9h 50m1 stop
Delta Logo
2:39 pm - 9:35 pmSJU-HOU
7h 56m1 stop
$215Delta
Find Deal
Sun, Aug 17 - Fri, Sep 5
Delta Logo
12:50 pm - 10:23 pmHOU-SJU
8h 33m1 stop
Delta Logo
6:15 am - 12:01 pmSJU-HOU
6h 46m1 stop
$255Delta
Find Deal
Sat, Jul 12 - Tue, Jul 15
American Airlines Logo
6:13 pm - 10:59 amIAH-SJU
15h 46m1 stop
American Airlines Logo
11:50 am - 5:19 pmSJU-IAH
6h 29m1 stop
$260American Airlines
Find Deal
Fri, May 16 - Tue, May 20
Southwest Logo
4:30 pm - 11:55 pmHOU-SJU
6h 25m1 stop
Southwest Logo
5:50 pm - 9:30 pmSJU-HOU
4h 40mnonstop
$336Southwest
Find Deal
Wed, May 21 - Thu, Jun 5
Southwest Logo
1:00 pm - 11:55 pmHOU-SJU
9h 55m2 stops
Southwest Logo
5:50 pm - 9:30 pmSJU-HOU
4h 40mnonstop
$350Southwest
Find Deal
Wed, May 21 - Thu, Jun 5
Useful Info

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 price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Houston to Caribbean Islands.

The cheapest ticket to Caribbean Islands from Houston found in the last 72 hours was to San Juan, at $137 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 72 hours was $137.

Can I save money by flying with a layover from Houston to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $664 on average.

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 September, when tickets cost $271 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $481 and $372 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, Monday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Caribbean Islands back to Houston, the best deals are generally found on Friday, 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 4 weeks before departure.


Good to know

Cheapest flight$55
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 AirlinesIAH-SJUSep 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 AirlinesIAH-POSDec 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.

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

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $260 on average. Morning departures are around 4% cheaper 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 $552.

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 4293 reviews
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
8.2Boarding
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

My suitcase was completed destroyed. The top part is broken and unusable now.

We boarded but then sat there waiting on some missed connection people to get on so we sat for about 15 minutes for that. Then we sat again because the passenger manifest was wrong and they had to figure it out before we could leave. That took about another 20 minutes or so. The crew was working hard to figure it out so it’s not their fault. It ended up being a system glitch where someone was upgraded to first class while another person was also in the same seat and it just created a mess that took a little while to figure out. They literally went to every person on the plane asking their names to see who was sitting in the wrong seat. I also hate the entertainment that must be watched on your phone or tablet. Just give us setback screens. It’s so much better. Almost every Delta flight has this now and it is so nice to have them. The crew did a great job. I have no complaints from them. They were very hard working, even with the mishap and a disgruntled passenger.

My priority checked bag was not loaded on the flight. I had to sit in baggage claim in Las Vegas for 2 1/2 hours waiting for the next flight. All baggage staff were very helpful, tracking showed it as scanned for loading. Nobody told me why it wasn't on my flight.

All male crew was just too woke for me. I felt like a sardine. I will never take a window seat or the rearmost seat again. I booked early and did not pay for seat selection and that was a mistake. The security at IAH was atrocious. I was violated and radiated as I was in a hurry to connect to my other flight. I may have lost items under the seat in front of me that I couldn't see nor bend over to look.

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

In general ok, my only issue is that they had no hot items for purchase. I had very little time in my connection due to baggage/customs/TSA, thag I barely even had a chance for a stop at the washroom and buy water, to make it to my gate when they started boarding. I had nothing to eat because the trip started early, so I was ready to purchase, and they had nothing except for dry items like snacks. I had to purchase a mediocre, overpriced cheese and fruit board, instead of at least a pizza or sliders that I was planning on getting. Other than that, it was fine. But that’s typical Air Canada, to not have enough.

How badly can you screw up baggage claim? We were told to go to baggage claim too for our bags from this flight. Another flights bags were there. They finished up. More bags from a different flight arrived. Our bags did not Finally the baggage claim belt stopped working and and are flight was still listed on the arrivals for that baggage claim 2. And then nothing It turns out that they had been delivered not only the United baggage claim but far away on a Delta baggage claim No I never told us. It was only the people looking around who had been on the flight But I’m sure there was plenty of time for the employees to raffle through the bags and steal whatever they wanted

Long wait before take off without an update for 20 minutes. Flight was good otherwise.

Flight delayed over 2 hours . I was flying bussiness never got food cause they ran out of what i wanted

Took off on time and successfully avoided weather that looked to be a problem along the way

I liked everything. Except that my neck was hurting on the seat. I couldn't sleep.

We were delayed Al ost / hours after boarding so that maintenance had to add oil to the engines. Then the oil they grabbed had been left out in the Dallas record cold and was frozen. They had to go back to the hanger and grab some that was not frozen.

They changed my seat from one that I had paid for as an upgrade to a regular seat at the last minute.

Flight was empty so had a whole row to myself. Still had to wait to get the bag due to the negligence at Palm Springs departure.

Everything was on time, we arrived early, everything worked well.

Angela was the best fa ever. She made that 8 hour flight a breeze

This was a pleasant, short flight and the crew was friendly.

The service and food needs to improve to catch up with other international flights

Small plane, so no entertainment. Hour delay! Nobody explained wht the delay was all about.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

The flight was on time. The seats are very narrow.

Unclear pricing; ended up being charged an extra $52 just to get onboard

Seats are poor. They do not lean back. They do not even have pockets on the back, making it impossible to store a phone or a coke bottle. If you opt for basic economy cheap seats, they stick you always in the middle or window seat, even though there are unoccupied seats on the aisle. And then there is the nickel and diming. No carry-ons. And checking your carry-on is $70. At the end there is no price advantage but there is plenty of aggravation.

Flight crew was great. Spirit leaves a lot to be desired in terms of comfort.

Worst Airplane ride I ever have taken... My purchased seat was changed without my consent

would be great to get basic water, soda at least and stop charging for carry ons

They changed our departure time 6 times before I even reached the airport. Delayed, Ontime, Delayed Back on time, Then Delayed. We finally boarded the plane and then we had to sit on the runway for over an hour only to be told they were taking us back to the gate for an additional 2 hour delay. Lack of communication and a complete waste of time! Never 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.

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