$88 Find Cheap Flights from Caribbean Islands 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 Hobby departing on 9/11. 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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1 adult, Economy

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Cheap Flights from Caribbean Islands to Hobby

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

Thu, Nov 13 - Sun, Nov 16
Southwest Logo
2:10 pm - 9:35 pmSJU-HOU
9h 25m1 stop
Southwest Logo
5:25 am - 5:05 pmHOU-SJU
9h 40m1 stop
$175Southwest
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Thu, Oct 2 - Tue, Oct 7
American Airlines Logo
1:37 pm - 11:48 pmSJU-HOU
11h 11m2 stops
American Airlines Logo
6:00 am - 2:25 pmHOU-SJU
7h 25m1 stop
$179American Airlines
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Thu, Oct 2 - Tue, Oct 7
Delta Logo
2:26 pm - 10:37 pmSJU-HOU
9h 11m1 stop
Delta Logo
6:00 am - 1:19 pmHOU-SJU
6h 19m1 stop
$225Delta
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Thu, Aug 14 - Sun, Aug 17
American Airlines Logo
6:00 am - 3:50 pmSJU-HOU
10h 50m2 stops
American Airlines Logo
6:00 am - 2:25 pmHOU-SJU
7h 25m1 stop
$240American Airlines
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Tue, Sep 30 - Tue, Oct 7
American Airlines Logo
6:10 am - 6:10 pmSJU-HOU
13h 00m2 stops
American Airlines Logo
6:00 am - 2:25 pmHOU-SJU
7h 25m1 stop
$245American Airlines
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Wed, Nov 12 - Sun, Nov 16
Southwest Logo
6:40 am - 7:45 pmSJU-HOU
15h 05m2 stops
Southwest Logo
5:25 am - 5:05 pmHOU-SJU
9h 40m1 stop
$263Southwest
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Thu, Aug 21 - Sun, Aug 24
Southwest Logo
11:10 am - 8:15 pmSJU-HOU
10h 05m2 stops
Southwest Logo
5:45 pm - 12:45 amHOU-SJU
6h 00m1 stop
$269Southwest
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Thu, Aug 14 - Sun, Aug 17
American Airlines Logo
1:36 pm - 10:12 pmSJU-HOU
9h 36m2 stops
American Airlines Logo
8:25 pm - 2:25 pmHOU-SJU
17h 00m1 stop
$280American Airlines
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Fri, Oct 10 - Tue, Oct 14
Delta Logo
7:15 am - 5:48 pmSJU-HOU
11h 33m1 stop
Delta Logo
6:00 am - 4:33 pmHOU-SJU
9h 33m1 stop
$293Delta
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Fri, Nov 14 - Sun, Nov 30
WestJet Logo
4:30 pm - 12:12 pmKIN-HOU
20h 42m2 stops
WestJet Logo
5:35 pm - 3:33 pmHOU-KIN
20h 58m2 stops
$1,832WestJet
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Good to know

Low seasonFebruary
Cheapest flight$88
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from San Juan to Houston Hobby Airport

FAQs for booking Caribbean Islands to Houston Hobby Airport flights

  • How does KAYAK find such low prices on flights from Caribbean Islands 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 Islands 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 Islands 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 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 Caribbean Islands 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 Islands with another airline.

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

 
Need help choosing which airline to fly with from Caribbean Islands to Hobby? 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 4246 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

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!

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Check in process was terrible. Lady at counter didn’t know what she was doing

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

The crew was amazing; Von, Vera and Guadalupe were very friendly and attentive throughout the entire flight. They were friendly and welcoming to everyone. A solid and dedicated team for sure!

Terrible. I was bumped off of my original flight and spent the next six days fighting to get back on it. I lost hours of my vacation trying to get this situation corrected.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

The woman gate agent in Phoenix was none too sympathetic about my check-in process as I am relatively new with using apps. I almost did not get on because she said I did not check-in. I thought I had via Kayak where I purchased a very expensive ticket. Lesson learned but to be told I may not get on as a matter of factly was difficult to hear.

Flight was on time. Boarding was smooth. Flight attendants were friendly and efficient. Entertainment system was broken for all passengers on the left side of the aisle. I would prefer if meals were not served on red eye flights. No one should need to dine at that time and it is disturbing for those passengers trying to sleep.

Gate agent did not hold flight for connection, provided no assistance to get new flight

I always appreciate when everything is on time! In this flight you have a short connection and it could be stressful , but is was easy and fast. They even ask people to wait so the ones that have a short connection could leave before. It was the fist time that something like this happened.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My suitcase was destroyed. The top part where the handle is is completed broken. And unusable now.

Since when do I have to pay for my checked bag? I have a United Explorer mileage plus silver card and I was charged for my checked bags. This also is an international flight. So I would like an explanation to be clear before I choose an airline please?

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

Pretty bad gate mgmt upon arrival. No open gates and we had to wait at midnight. Shouldn’t be a surprise that an aircraft is coming in.

Comfortable plane ride however on delays disappointment no real details as to why the delays when other flights are leaving the airport

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

EVERYTHING! It was so bad that I will be filing a claim for reimbursement for my seat as I could not fully sit in it due to an obese person being next to me and spilling over into my "space." And my personal item in the overhead been got crushed between two suitcases, so now my business laptop has been damaged beyond repair. Also, it was expensive! Since you pay for EVERYTHING, the cost of the trip was probably more than if you I used an airline that was not discounted. I will NEVER fly Spirit Airlines again!

One of worst experienc my family have every had with this airline. I was informed my Kayak that my flight was delayed and that my family will not make it to houston for our connecting flight. I contacted Spirit customer service to get my family on a later flight due to the delay in Vagas and them not making their connecting flight. The customer rep keep telling me that the flight from vagas is on time and not delayed. She even make to go to the spirit app on my phone and show me how to look up weather or not the flight was delayed. The app showed "on time" 20 minutes later when my family arrived at the airport for their flight, they were told that the flight was delayed and she will not make her connecting flight. I call spirit airline customer support again that night and spoke to another rep who apologize for his collegue and he told me that my family will receive a credit for this, this was on Saturday I still have not received the credit or an email letting me know when I will be credited for this inconvenience. This is not good business and it need to be fixed.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

Flight delayed over 3 or 4 hours because no captain to fly plane. I couldn’t make a connection and had to wait 9 hours for another flight. Had to fly red eye flight. Sucks

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

We had an almost 7 hour flight delay. We left the gate twice and taxi-ed and then returned the gate twice. Finally we got a new flight crew (our third one) and then left the gate to the final time before departing at 6:45pm (original flight time was 12pm). Out of Newark.

First off, i received an e-mail to allow me to check in for our flight. I folllowed the link, when it came to the seat selection, I was unable to select any "free" seats ( meaning without any additional charge) because everything was " unavailable". My Husband and I were ttavelling with our 3 children hence, i wanted to be assured that we were all seated next to each other. I tried 3 times and everytime I click the selection it said " error loading". What the system wants is for me to buy the seats ( anywhere from $25 to $50 dollars each passenger) like I did on our flight bound to L.A. I called customer service and the guy was unhelpful all he kept repeating was to come really early at the airport and we will be assigned seats there. Imagine my anxiety!!! Spirit says they are a budget airline but they are actually the opposite!! And just before our flight, the flight attendant KEPT announcing/ selling the seats that were not purchased for a cheaper price!! Like it was a bidding/ bargaining game! This was our first and last time to fly Spirit.

My flight got cancelled by Spirit airlines, it was bad experience to me

Spirit gets you there; it's no worse than any other aircraft, all things considered. (It's not like everyone else is such a hero). But - holy moses - do they nickel and dime you to absolutely every nickel - I was really expecting to have to pay to use the bathroom. And when the captain comes on with a 5 minute sales pitch about getting "points", that was like something on Bizarro world. Other than that, everyone else was professional and worked hard to get us from point A to point B. I'm not loving all the "self-service" stuff but there it is - just when the machines don't work you don't have anyone to talk to.

Easy boarding and good flight. Need to work on the beverage and snack situation

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