$180 Find Cheap Flights from Caribbean to Houston Hobby Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Houston departing on 5/23. 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

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Cheap Flights from Caribbean to Houston

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Houston 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 Caribbean to Houston

Fri, May 8 - Sun, May 10
Southwest Logo
6:50 am - 6:35 pm
SJU
-
HOU
12h 45m
2 stops
Southwest Logo
5:05 am - 12:00 pm
HOU
-
SJU
5h 55m
1 stop
$364Southwest
Fri, Apr 24 - Sun, Apr 26
Southwest Logo
2:00 pm - 11:10 pm
SJU
-
HOU
10h 10m
2 stops
Southwest Logo
8:45 pm - 12:10 pm
HOU
-
SJU
14h 25m
1 stop
$382Southwest
Thu, May 7 - Mon, May 11
Southwest Logo
1:00 pm - 9:10 pm
SJU
-
HOU
9h 10m
1 stop
Southwest Logo
1:20 pm - 11:25 pm
HOU
-
SJU
9h 05m
2 stops
$384Southwest
Fri, Apr 24 - Sun, Apr 26
Southwest Logo
2:00 pm - 11:55 pm
SJU
-
HOU
10h 55m
2 stops
Southwest Logo
2:35 pm - 11:45 pm
HOU
-
SJU
8h 10m
2 stops
$400Southwest
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
11:59 pm - 9:26 am
SJU
-
HOU
10h 27m
1 stop
American Airlines Logo
4:18 pm - 4:32 am
HOU
-
SJU
11h 14m
1 stop
$402American Airlines
Wed, Apr 1 - Wed, Apr 8
Delta Logo
1:00 pm - 10:42 pm
SJU
-
HOU
10h 42m
1 stop
Delta Logo
2:13 pm - 11:15 pm
HOU
-
SJU
8h 02m
1 stop
$405Delta
Wed, Apr 8 - Wed, Apr 15
American Airlines Logo
11:59 pm - 9:26 am
SJU
-
HOU
10h 27m
1 stop
American Airlines Logo
8:21 pm - 4:32 am
HOU
-
SJU
7h 11m
1 stop
$407American Airlines
Fri, May 1 - Tue, May 5
Delta Logo
3:28 pm - 11:07 pm
NAS
-
HOU
8h 39m
1 stop
Delta Logo
10:53 am - 4:33 pm
HOU
-
NAS
4h 40m
1 stop
$567Delta
Thu, Apr 16 - Wed, Apr 22
WestJet Logo
3:30 pm - 4:28 pm
KIN
-
HOU
24h 58m
2 stops
WestJet Logo
5:23 pm - 2:30 pm
HOU
-
KIN
21h 07m
2 stops
$992WestJet
Fri, May 22 - Mon, May 25
WestJet Logo
3:30 pm - 4:09 pm
KIN
-
HOU
24h 39m
2 stops
WestJet Logo
5:02 pm - 2:30 pm
HOU
-
KIN
45h 28m
2 stops
$1,365WestJet
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$180
Most popular time to fly with an average 11% increase in price.
Flight from San Juan to Houston Hobby Airport

FAQs for booking Caribbean to Houston Hobby Airport flights

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

    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 Caribbean to Houston Hobby Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Houston Hobby Airport from Caribbean 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 Caribbean to Houston Hobby Airport?

    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 to Houston Hobby Airport with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Houston Hobby Airport?

    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 to Houston Hobby Airport from Caribbean 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 Caribbean to Houston

 
Need help choosing which airline to fly with from Caribbean to Houston? 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
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

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

6.0 GoodChris, Mar 2026
DAL - SAT
Read more Southwest reviews

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

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

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

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

No delays and arrived to destination 30 min early. Staff was super friendly.

Everything a cheap airline should be at normal airline rates.

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!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

I wish the inflight entertainment system options were broader, but overall this was a fantastic crew and I can’t express how cheerful, welcoming, and attentive they were.

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Crew was tired as we all were. Pretty abrupt. Flight was delayed. Not as enjoyable as the other 3 legs we flew.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Good until I was put on air canada flight Houston Vancouver not even one cookie

Very old flight - time to retire it for newer airplanes

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

I guess if you don't run the AC it saves on fuel? Everyone complained the entire trip about how hot the cabin was. Also, extremely cramped. AA allows a little space per passenger as is legal. Not cheap, ticket prices were high.

The flight attendants and the service is getting worse by the day.

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

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

The flight attendants as well as the gate agent were out to lunch. Nothing extraordinary about their service. American just keeps getting worse every year.

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

I am an AA flyer for a very long time... AA has yet to disappoint.

Arriving plane went to wrong gate. Flight Attendant was late. Was in no Hurry when he arrived. Flight was fine. Plane had to wait 20 minutes to get assigned a gate due to designated gate tied up. barely connected.. Boarded extremely late on final leg of trip.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

My flight was delayed by over an hour and the turbulance was horrible.

This flight cancelled. I am in the airport right now and my kids sleep on the floor. We are waiting for information in the line 4 hours and rude woman from spirit airline offers us flight to Austin on 23 February. No water no food offer. The offer to book hotel and they will refund 150$. The nearest hotel 450$ per night. So I got flight to San Antonio 02/22 at 7am. I hate this company, they are rude and no empathy. So many people with kids were there. And I don’t sleep and it is cold here. I don’t have warm clothes for me and my kids. And I don’t have money for transport from San Antonio to my Austin.

The flight was delayed over an hour which got us into DFW at approximately 2:20 am

Terrible. Spirit cancelled the flight with 3 hours notice and were absolutely no help getting another flight. Had to make my own reservation on another airline and arrived in Dallas 12 hours later.

They cancelled the flight due to crew unavailability. The next day they cancelled the flight again.

That gate is like a ducking shelter at Newark No where to sit Outlets that don’t work Bathrooms that are dirty

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

Horrible experience. First and last time using this airline. Made an announcement that boarding will start in 15 minutes, canceled the flight 5 minutes later due to no airline staff. Had to book another flight on Delta since Spirit had no other flights arriving to my original destination the same day. I wouldn't recommend anyone to fly with Spirit. No wonder why it consistently ranks high among worst airlines.

The plane was supposed to leave at 12:59 Amma and another plane took us around 9:30 am. There were 7 delay announcements. We were to receive a voucher of $12 back to pay for food at any place in the airport. One passenger tried to use the voucher was denied. I did not receive the voucher for me, my son, and grandson. I went to the desk and informed them and they took my phone # and email and they told me to wait. I did and was never sent. The plane was uncomfortable, the crew was dismissive of anyone beyond the last two seats. I will NEVER fly or recommend Spirit Airlines again.

I knew what I was getting into, but never again. Hour long bag drop. 1.5 hour delay. 1 hr 45 mins sitting on the tarmac after landing. They lost a bunch of bags but luckily not mine. Awful experience.

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