$103 Find Cheap Flights from Houston Hobby Airport 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 Hobby to Caribbean Islands departing on 1/24. 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 Hobby to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$498
Santo Domingo
Santo Domingo1 stop$563
Montego Bay
Montego Bay1 stop$419
Oranjestad
Oranjestad1 stop$616
Nassau
Nassau1 stop$535
Kingston
Kingston1 stop$595
Simpson Bay
Simpson Bay2 stops$582
Providenciales
Providenciales1 stop$525
Port of Spain
Port of Spain2 stops$563
Bridgetown
Bridgetown1 stop$601
George Town
George Town1 stop$484
Willemstad
Willemstad2 stops$553
St. John's
St. John's1 stop$629
Puerto Plata
Puerto Plata2 stops$572
Punta Cana
Punta Cana1 stop$498
Santo Domingo
Santo Domingo1 stop$563
Montego Bay
Montego Bay1 stop$419
Oranjestad
Oranjestad1 stop$616
Nassau
Nassau1 stop$535
Kingston
Kingston1 stop$595
Simpson Bay
Simpson Bay2 stops$582
Providenciales
Providenciales1 stop$525
Port of Spain
Port of Spain2 stops$563
Bridgetown
Bridgetown1 stop$601
George Town
George Town1 stop$484
Willemstad
Willemstad2 stops$553
St. John's
St. John's1 stop$629
Puerto Plata
Puerto Plata2 stops$572

Book Cheap Hobby 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 Hobby 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 Hobby to Caribbean Islands

Sun, Jan 18 - Tue, Jan 27
Delta Logo
5:35 am - 5:17 pmHOU-SJU
9h 42m1 stop
Delta Logo
7:30 am - 4:12 pmSJU-HOU
10h 42m1 stop
$224Delta
Find Deal
Tue, Dec 9 - Sat, Dec 13
Southwest Logo
11:30 am - 9:30 pmHOU-SJU
8h 00m2 stops
Southwest Logo
8:20 am - 2:40 pmSJU-HOU
8h 20m1 stop
$270Southwest
Find Deal
Tue, Dec 2 - Thu, Dec 4
Southwest Logo
1:35 pm - 12:35 amHOU-SJU
9h 00m2 stops
Southwest Logo
3:55 pm - 8:55 pmSJU-HOU
7h 00m1 stop
$280Southwest
Find Deal
Tue, Dec 9 - Sat, Dec 13
American Airlines Logo
9:02 am - 9:25 pmHOU-SJU
10h 23m1 stop
American Airlines Logo
6:54 am - 5:59 pmSJU-HOU
13h 05m1 stop
$290American Airlines
Find Deal
Sun, Jan 18 - Thu, Jan 22
Delta Logo
5:35 am - 5:17 pmHOU-SJU
9h 42m1 stop
Delta Logo
3:55 pm - 10:35 pmSJU-HOU
8h 40m1 stop
$310Delta
Find Deal
Sat, Nov 15 - Fri, Nov 21
Southwest Logo
11:05 am - 5:15 pmHOU-SJU
4h 10mnonstop
Southwest Logo
6:40 am - 1:35 pmSJU-HOU
8h 55m1 stop
$311Southwest
Find Deal
Mon, Jan 19 - Wed, Jan 28
Delta Logo
5:35 am - 2:30 pmHOU-SJU
6h 55m1 stop
Delta Logo
7:30 am - 4:12 pmSJU-HOU
10h 42m1 stop
$313Delta
Find Deal
Sat, Nov 15 - Fri, Nov 21
Southwest Logo
10:55 am - 6:40 pmHOU-SJU
5h 45m1 stop
Southwest Logo
6:40 am - 1:35 pmSJU-HOU
8h 55m1 stop
$315Southwest
Find Deal
Sun, Dec 7 - Fri, Dec 12
American Airlines Logo
6:29 pm - 5:19 amHOU-SJU
8h 50m1 stop
American Airlines Logo
7:00 am - 5:59 pmSJU-HOU
12h 59m1 stop
$329American Airlines
Find Deal
Sat, Nov 29 - Fri, Dec 5
British Airways Logo
6:22 pm - 3:52 pmHOU-UVF
19h 30m2 stops
British Airways Logo
4:00 pm - 9:38 amUVF-HOU
19h 38m2 stops
$753British Airways
Find Deal
Booking Insights

KAYAK's insights & trends for Hobby to Caribbean Islands flights

Get data-powered insights and trends into flights from Hobby to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Houston Hobby Airport 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 Hobby Airport found in the last 72 hours was to Punta Cana, at $661 round-trip. The most popular route is from Houston Hobby Airport (HOU) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $829.

Can I save money by flying with a layover from Houston Hobby Airport 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.

No, with an average price for the route of $407, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Houston Hobby Airport 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 Hobby Airport 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 Hobby Airport to Caribbean Islands is April, when tickets cost $282 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $485 and $393 respectively.

What’s the cheapest day of the week to fly from Houston Hobby Airport to Caribbean Islands?

The average price of all round-trip flights from Houston Hobby Airport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Houston Hobby Airport to Caribbean Islands, look for departures on Sundays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean Islands, Saturday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Houston Hobby Airport 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 Hobby Airport 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 Hobby Airport 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

Low seasonSeptember
Cheapest flight$103
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Houston Hobby Airport to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Houston Hobby Airport 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 Hobby Airport to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Houston Hobby Airport to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Houston Hobby Airport 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 Hobby Airport 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 Hobby Airport 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 Hobby Airport 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 Hobby Airport 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 $253 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 $500.

Reviews of the top 5 airlines serving from Hobby 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 Hobby 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 4241 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Crew was excellent. This was a relatively long flight though and had very little leg room, and no entertainment.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Plane was crowded and even when we hit altitude, the plane was hot, not enough air flow.

Flight was delayed and missed my connection Lufthansa didn’t respond.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

Overall it was good. I missed my connection but I was put on another flight.

Although the flight was delayed the crew and the flight itself were very good. Couldn't fault anything and after the disappointment of being abandoned in the US by BA it was a welcome relief to travel with United

Boarding experience was smooth. Flight attendants were friendly and helpful. Entertainment system on the Houston-Edmonton flight did not function for passengers on the left side of the aisle. On the bird's eye flight from Quito to Houston, they should not serve a meal. No one needs to eat after midnight and it is disturbing for those passengers trying to sleep.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

The only thing to like was that we eventually got to our destination

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

We were delayed for a “couple of maintenance issues.” They were resolved rather quickly but a computer glitch caused someone in the airport to have to bring a physical copy of the paperwork so we could leave. I don’t know where they had to drive from to get to our plane but it took forever & we were 1 1/2 hrs late in leaving. The flight itself was fine.

We didn't take off until an hour after we boarded.

The flight was fine. This survey is not. There is no option for N/A so items which don’t apply to my experience still must be rated. In those instances I give a “3” rating which ultimately skews the results.

The actual trip was fine, however, the changes made to our flights and the layovers were had to endure were awful.

Flight from Dallas to OKC was good, but my trip was interrupted due to a delayed flight from Austin to DFW, which happens all the time. I frequently miss my connection from DFW and American can never seem to make this work!

Because the plane was 90 degrees F, they would not let us board. I wish they had, because it meant we were delayed. It's Texas, of course it's hot. We would have survived.

Always comes in handy when I want a quick weekend getaway.

The entire staff from check in agents to flight attendants were pleasant and professional. Would suggest a complimentary water.

Spirit is low fare air line. Food also cost you. No free food.

Everyone was kind for the most part. I did travel with children and paid for seats and even then it was not as suitable. I tried calling their customer service prior to check in and I was told they couldn't help me because I didn't purchase my tickets with them.

I think the staff was nice. They took time to explain safety protocols. Boarding was great. They started early and our flight left a little early which was convenient. Having free games to play would have been better

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

Better than my las vagas experience, but still dissapointed with the airline support service.

Unfortunately, spirits crew had us boarding and parking the plane often, would wait long periods of time before allowing the people attending the flight on the plane to know what was going on this caused for my plane to not only get diverted but then canceled at an airport 2 hours away and basically stranded with charter buses MAYBE being hired. I was left with no choice but to stay overnight and use a comp room in Altantic City to then arrive home the next day. This trip was the first time seeing my partner since he joined the Air Force and this stressful ride caused unwarranted tears on what was supposed to be an east flight home. I understand weather is unpredictable but to have passengers deboard to then reboard an hour later to taxi on the runway for another hour to then basically leave an entire fight stranded. I waited almost 30 minutes at the airport and not one employee could tell me about a charter bus so I had to leave and make accommodations to stay overnight and get a ride home.

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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