$188 Find Cheap Flights from Caribbean to Houston Hobby Airport - Compare and Save

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 9/16. 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, Aug 21 - Mon, Aug 24
Southwest Logo
6:00 am - 11:05 am
SJU
-
HOU
6h 05m
1 stop
Southwest Logo
4:50 pm - 11:50 pm
HOU
-
SJU
6h 00m
1 stop
$381Southwest
Fri, Aug 21 - Mon, Aug 24
Southwest Logo
5:30 am - 8:00 pm
SJU
-
HOU
15h 30m
2 stops
Southwest Logo
5:05 am - 1:45 pm
HOU
-
SJU
7h 40m
1 stop
$381Southwest
Fri, Aug 21 - Mon, Aug 24
Southwest Logo
5:30 am - 8:00 pm
SJU
-
HOU
15h 30m
2 stops
Southwest Logo
10:00 am - 10:50 pm
HOU
-
SJU
11h 50m
2 stops
$381Southwest
Fri, Sep 4 - Sun, Sep 6
Delta Logo
2:59 pm - 10:05 pm
SJU
-
HOU
8h 06m
1 stop
Delta Logo
6:00 am - 1:42 pm
HOU
-
SJU
6h 42m
1 stop
$386Delta
Thu, Sep 3 - Mon, Sep 7
Delta Logo
7:00 am - 4:25 pm
SJU
-
HOU
10h 25m
1 stop
Delta Logo
6:00 am - 1:42 pm
HOU
-
SJU
6h 42m
1 stop
$386Delta
Thu, Sep 3 - Thu, Sep 10
Delta Logo
7:00 am - 4:25 pm
SJU
-
HOU
10h 25m
1 stop
Delta Logo
2:25 pm - 10:19 pm
HOU
-
SJU
6h 54m
1 stop
$386Delta
Thu, Oct 8 - Mon, Oct 12
American Airlines Logo
6:00 am - 4:36 pm
SJU
-
HOU
11h 36m
1 stop
American Airlines Logo
6:00 am - 11:20 pm
HOU
-
SJU
16h 20m
1 stop
$411American Airlines
Tue, Sep 22 - Sat, Sep 26
American Airlines Logo
6:00 am - 3:43 pm
SJU
-
HOU
10h 43m
2 stops
American Airlines Logo
6:04 am - 2:45 pm
HOU
-
SJU
7h 41m
1 stop
$411American Airlines
Fri, Nov 20 - Sat, Nov 28
JetBlue Logo
11:20 am - 5:20 pm
SJU
-
HOU
8h 00m
1 stop
JetBlue Logo
11:00 am - 5:10 pm
HOU
-
SJU
4h 10mnonstop
$527JetBlue
Wed, Nov 25 - Mon, Nov 30
JetBlue Logo
5:35 am - 4:05 pm
SJU
-
HOU
12h 30m
1 stop
JetBlue Logo
12:30 pm - 9:45 pm
HOU
-
SJU
7h 15m
1 stop
$531JetBlue
Useful Info

Good to know

Low season

February

Cheapest flight

$188
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 6% 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 4228 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

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!

4.0 OkayAnonymous, May 2026
MSY - HOU
Read more Southwest reviews

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!

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

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

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.

Was good. I miss the free 2 checked bags. That was part of what made Southwest special

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

Easy to book and to get check in and get on and off.

First time I’ve ever missed a flight and it was an international flight.. Southwest put me on the next flight and it was the best experience possible.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Smaller plane for a longer flight than my first one. Doesn’t make sense.

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.

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Only freetext wifi was available in flight; browsing WiFi required payment. Since the seats had no in flight entertainment, Delta should revisit this policy on this longer flight.

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

The entertainment screens were not working and there was no air condition the entire flight. Very uncomfortable.

Lounge in Lagos is terrible, food on board from Lagos to Atlanta was horrible. Only bright spot the cabin crew were awesome.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Great!! I haven’t had a bad experience with them.

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

The international portion was good. Food and beverage options were good. The sustainable wooden eatery was less than desirable. Your Star Alliance partner ANA provided real silverware. I'm 6'3" & 198 lbs and felt cramped in the exit row. How can that be? Flight attendant all had a pleasant disposition which is always good.

The staff were polite and professional. I found the boarding for First Class Business customers not great. They didn't offer me pre- boarding. Just regular zone 1 boarding which didn't feel great. On board and throughout all of our United Flights we found the staff wonderful. We'll definitely fly United again.

Boarded from a very small gate at LAX. Staff at gate had us line up, then waited 25 minutes to board without a word of explanation. Plane arrived on time then waited 20 minutes for a plane to vacate our gate. Majority of bags arrived after 15 minutes but it took an hour for a small number of remaining bags to be off-loaded despite my “priority” bag tag.

The boarding process on the departure from LA was rather slow even though I was in Group 1. For first class, I was not expecting to have to pay for Wi-fi but I did and then the wi-fi was spotty. The entree was surprisingly good and so that was a pleasant surprise. However, once I got to Houston, it was terrible. Unfortunately there was bad weather but the constant gate changes for my connecting flight was difficult to manage due to having to navigate back and forth between different terminals.

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

The flight was delayed, they didn’t even have water for the toilets or for drinks

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

The flight had a delay but I made it to my connection. Flight was smooth overall

The flight to Houston the agents were not very helpful

The flight was ok, i understand Houston-Dallas is a short distance. The plane is really small: no TV, no snacks, but other than that, all was good. We had a bid delay but luckily it did not affect my connection

My flight was delayed by 8 hours I arrived at airport 4hrs earlier but to see if they can reroute me to get my connecting flt to Hong Kong. They auto rebooked my flt. With no chance. Which I missed this entire reservation through kayak. My next flt they got me on was at 6 am. Misses an entire day of my trip abroad all my accommodations seat assignments were missed and missed adding my TSA precheck to my ticket as well as my vegan meal request so I didnt have meals on any of the flight....so not a comfortable experience. Please help me with accommodations upon my return.

Not good. Flight crew, was not friendly and just shoved stuff at us. Not the way I like to travel.

They kept us on the tarmac for 6 hours after already delaying our flight by 2 hours. No one had any answers. They sent our gate checked stroller to baggage claim instead of giving it back at the gate.

The plane was very creaky and lots of ringing. Plane was dirty and dingy. I couldn't hear the captain's announcements from the flight deck. Not sure if it was the captain or the audio equipment, but good thing there wasn't an emergency where we needed clear instructions. The overhead compartments were clearly full, but the flight crew allowed people to stand in the back with their carry on luggage. Then after everyone boarded, they had to go to the front to gate check their luggage because there was no room for their bags and then they returned to their seats...such a waste of time when clearly the overhead compartments were full when they originally boarded.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Awful. We had an 8 hour mechanical delay- no vouchers and no kind/courtesy/professional representatives in the entire airport. Not only was it a terrible experience for both my 7 year old and myself, I still have not heard back from American about how they’re going to correct it- I’ve sent 2 or 3 emails about our experience- which was just awful. Not to mention according to national traveling laws, we should be reimbursed… but of course they’re not responding.

Overall it was good but not great. The aircraft was an old and seats didn’t recline in business class unless you kept playing around with it.

The plane was subbed for another last minute, the gate was changed last minute. Could live with that but we boarded and there was a delay which totaled an hour in the end. There was a technical issue which meant wheels needed to remain out for ten mins after take off. My USB phone charger was broken as was the headphone jack which meant I could t enjoy the IFE and could use my phone after a few hours. Even the map function on the plane failed to work after a few hours.

The flight was delayed and we were told the airplane is on its way to the gate from the hangar. We were told this for 2 hours and the flight was continually delayed in ~30 minute increments. Then we ended up having a new airplane. The issue wasn’t clearly communicated and it left everyone feeling confused about when we would actually be leaving. Whenever they communicated a new boarding time it felt arbitrary and random. The boarding process was a mess and disorganized, which made it last longer than necessary. Landing was rough. Seats were uncomfortable.

Terrible. Delayed my family flight for several hours affecting family plans

Flight was delayed and then my second leg was completely canceled. Had to get a refund

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

My flight was canceled I was promised a reginf still not received.

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

Very delayed with little to no communication from the captain or flight crew. All announcements made were not audibly understood by passengers. Very poor communication. After arrival it took approximately 20 minutes to get a jet bridge to the plane.

I fly Frontier often and generally don't have any issues. For some reason, the Denver to Houston's George Bush Intercontinental (IAH) flight always needs to wait on the tarmac in Houston because a gate is not available after landing. I've been stuck for as little as 15 minutes and as much as a little over an hour. I know only fly the Frontier Denver to IAH route when there is not an available flight to Houston Hobby (HOU).

Terrible Y lost my connection to Mexico, nobody of your company help me And y pay a lot of money for my baggage Until now I continue in the Houston airport I vneed you return my money

Everything was good, 20/30 minutes late waiting on a crew member. It’s hard to keep employees. Or serious employees I know. I remember one flight from Houston of Frontiers was almost 18 hours late. And another 4 hours late very poor. But I would rather be late and safe than the on the news. Thank you.

Good - Leg spar, cleanliness, and on time performance. Bad - No snacks and entertainment.

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