$182 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 4/14. 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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Flight Deals

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$425
Santo Domingo
Santo Domingo1 stop$653
Montego Bay
Montego Bay1 stop$460
Oranjestad
Oranjestad2 stops$533
Nassau
Nassau1 stop$520
Kingston
Kingston1 stop$684
Simpson Bay
Simpson Bay1 stop$521
Providenciales
Providenciales1 stop$471
Port of Spain
Port of Spain2 stops$634
Bridgetown
Bridgetown1 stop$692
George Town
George Town1 stop$467
Willemstad
Willemstad2 stops$643
Puerto Plata
Puerto Plata2 stops$628
St. John's
St. John's2 stops$655
Punta Cana
Punta Cana1 stop$425
Santo Domingo
Santo Domingo1 stop$653
Montego Bay
Montego Bay1 stop$460
Oranjestad
Oranjestad2 stops$533
Nassau
Nassau1 stop$520
Kingston
Kingston1 stop$684
Simpson Bay
Simpson Bay1 stop$521
Providenciales
Providenciales1 stop$471
Port of Spain
Port of Spain2 stops$634
Bridgetown
Bridgetown1 stop$692
George Town
George Town1 stop$467
Willemstad
Willemstad2 stops$643
Puerto Plata
Puerto Plata2 stops$628
St. John's
St. John's2 stops$655

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, May 3 - Sun, May 10
Southwest Logo
8:35 pm - 9:10 am
HOU
-
SJU
11h 35m
1 stop
Southwest Logo
12:50 pm - 9:50 pm
SJU
-
HOU
10h 00m
1 stop
$364Southwest
Thu, May 14 - Sun, May 17
Southwest Logo
8:00 am - 8:00 pm
HOU
-
SJU
11h 00m
1 stop
Southwest Logo
9:45 pm - 8:35 am
SJU
-
HOU
11h 50m
1 stop
$382Southwest
Tue, Apr 28 - Mon, May 4
Southwest Logo
2:50 pm - 11:40 pm
HOU
-
SJU
7h 50m
1 stop
Southwest Logo
1:00 pm - 9:10 pm
SJU
-
HOU
9h 10m
1 stop
$384Southwest
Sun, May 3 - Sat, May 16
American Airlines Logo
9:57 am - 11:02 pm
HOU
-
SJU
12h 05m
1 stop
American Airlines Logo
11:59 pm - 9:26 am
SJU
-
HOU
10h 27m
1 stop
$391American Airlines
Mon, Apr 20 - Sat, Apr 25
American Airlines Logo
4:18 pm - 4:32 am
HOU
-
SJU
11h 14m
1 stop
American Airlines Logo
11:59 pm - 9:26 am
SJU
-
HOU
10h 27m
1 stop
$409American Airlines
Sun, May 3 - Sat, May 16
American Airlines Logo
9:57 am - 11:02 pm
HOU
-
SJU
12h 05m
1 stop
American Airlines Logo
11:59 pm - 9:26 am
SJU
-
HOU
10h 27m
1 stop
$416American Airlines
Fri, May 8 - Tue, May 12
American Airlines Logo
6:01 am - 4:25 pm
HOU
-
PUJ
9h 24m
1 stop
American Airlines Logo
5:25 pm - 9:26 am
PUJ
-
HOU
17h 01m
2 stops
$425American Airlines
Sun, Apr 26 - Fri, May 8
Delta Logo
6:00 am - 12:54 pm
HOU
-
MBJ
6h 54m
1 stop
Delta Logo
1:18 pm - 10:26 pm
MBJ
-
HOU
9h 08m
1 stop
$460Delta
Sat, May 16 - Thu, May 21
Delta Logo
6:00 am - 3:34 pm
HOU
-
MBJ
9h 34m
1 stop
Delta Logo
2:21 pm - 10:26 pm
MBJ
-
HOU
8h 05m
1 stop
$493Delta
Wed, May 6 - Tue, May 12
Delta Logo
6:00 am - 11:48 am
HOU
-
NAS
4h 48m
1 stop
Delta Logo
1:16 pm - 10:26 pm
NAS
-
HOU
10h 10m
1 stop
$576Delta
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 San Juan, at $466 round-trip. The most popular route is from Houston Hobby Airport (HOU) 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 $466.

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

The average price for all round-trip flights from Houston Hobby Airport 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 $252 on average. Morning departures are around 21% 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 $498.

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 $434, 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 $315 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $494 and $415 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, Thursday is the cheapest day to fly and Monday 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 2 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$180
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Houston Hobby Airport to Montego Bay

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.

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 4317 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

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

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

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

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

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.

Airport terminal was outdated, flight was on a small jet with no wifi

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

The power at the seat didn't work and the seat itself was difficult to adjust - this was a business class seat. Flight attendant gave me miles to compensate. The attendant was very professional and on top of his game the entire flight.

I like flying first class, and United has a nice one

Unbelievably poor service from flight attendants. They didn’t even do water service on a four hour flight. Just disrespectful.

Seats had less pitch than a regional jet. Food was OK. Have to buy alcohol on US based carriers flying international. Boarding was a mess. Did not have bags but overhead space was gone quick. Would like to see the airlines enforce the one bag over and one bag under policy

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.

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Poor communication ahead of time about flight delays and old planes/other equipment.

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

The crew was excellent and overall the flight was good. No complaints.

Like all of the flights I took to get down to Dallas. They were delayed

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

When I arrived at the airport at 4:00 in the morning, I was notified that I "hadn't paid" for my ticket (I had paid and had a boarding pass). Then I was told that while I had paid, the ticket was $600 more than it actually was, and that I needed to pay that so I could board. None of this was true, of course, but it took 20 minutes, two crew members behind the desk, and one on the phone to clear up.

First off, I had a conversation with a flight attendant that was working this flight. I overheard her telling another flight attendant while we were in line for Chic-Fil-A that the flight was not going to land until 12:47 pm. I found this odd since the flight was to take off at 1:03. I commented to the flight attendant that was going to mess up the on-time take-off She said. if you fly alot you will notice that it's a good thing if the flight even arrives at all. I said that was a low bar. I think that flight attendants represent their airlines whether on board or in the airport ordering food. I was surprised to hear such negativity. However, I have noticed that Spirit flight attendants are usually in a sour mood.. Eventually the flight arrived and I boarded and the flight took off an hour late. There was no direction about the on-board wi-fi. Nor was there any info in the seat back pocket. I don't know if there was wi-fi or not, There were no complimentary snacks or drinks for my row 36 as there was turbulence and the captain asked the flight attendants to stop serving just as they were close to my row. When the turbulence stopped, they did have time to serve us but they did not. Upon arriving, the flight attendant asked anyone not having to catch a flight to Ft. Laudersle which was a tight connection to sit down and let those people pass. I complied but I could not help thinking that if Spirit would have took off on time that they would not have to inconvenience their passengers. All in all, I think Spirit is a mediocre airline at best. There are so many things they could do to improve. Yet, since I only fly Spirit infrequently preferring Southwest and Delta, I like to see if they are improving and sadly no, they are not. One good thing - nice modern seats and interiors.

My flight was cancelled I missed time at work and got a parking ticket

Went as planned. No wifi included and no screens. No free snacks. Didn't buy food so can't rate that. Unable to charge devices on plane. Staff were friendly and flight was fast, cheap and convenient.

I purchased extra legroom so I will be comfortable but the guy behind me is a big guy who keeps on moving and since he is big I can feel his movement at the back of my chair.

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Sadly there was a crew member very rude with my kid and with me.

They canceled the flight and didn't assist in getting a new flight on any airline. I had to spend 10 hrs in the airport after getting a ticket On Delta for twice as much. I've flown Spirit many times and this was my worst experience I've had.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

We had too many delays for the crew not the plane

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports