$178 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 5/9. 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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Everything you should know

Cheapest round-trip
$364
Overall average: $385
Southwest
Tue 2/24Wed 2/25
SJU - HOU • 1 stop
Cheapest non-stop
$407
Typical prices: $238-$485
Southwest
Wed 7/1Sun 7/5
SJU - HOU • Non-stop
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Flight Deals
Useful Info
Flight Deals

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

Tue, Feb 24 - Wed, Feb 25
Southwest Logo
9:05 am - 7:45 pm
SJU
-
HOU
12h 40m
1 stop
Southwest Logo
1:35 pm - 12:35 am
HOU
-
SJU
9h 00m
2 stops
$364Southwest
Fri, May 8 - Fri, May 15
Delta Logo
7:30 am - 4:26 pm
SJU
-
HOU
9h 56m
1 stop
Delta Logo
1:00 pm - 10:54 pm
HOU
-
SJU
8h 54m
1 stop
$390Delta
Sat, Apr 25 - Mon, Apr 27
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
$395American Airlines
Sat, Apr 25 - Mon, Apr 27
American Airlines Logo
6:47 am - 7:51 pm
SJU
-
HOU
14h 04m
1 stop
American Airlines Logo
8:21 pm - 4:32 am
HOU
-
SJU
7h 11m
1 stop
$401American Airlines
Wed, Jul 1 - Sun, Jul 5
Southwest Logo
6:30 am - 10:05 am
SJU
-
HOU
4h 35mnonstop
Southwest Logo
6:30 pm - 11:55 pm
HOU
-
SJU
4h 25mnonstop
$407Southwest
Wed, Jul 1 - Sun, Jul 5
Southwest Logo
5:00 am - 1:15 pm
SJU
-
HOU
9h 15m
1 stop
Southwest Logo
6:30 pm - 11:55 pm
HOU
-
SJU
4h 25mnonstop
$412Southwest
Thu, Apr 9 - Tue, Jun 30
Southwest Logo
6:50 am - 10:50 pm
SJU
-
HOU
17h 00m
2 stops
Southwest Logo
5:00 am - 2:55 pm
HOU
-
SJU
8h 55m
1 stop
$416Southwest
Tue, Mar 3 - Sun, Mar 8
JetBlue Logo
3:42 pm - 10:28 pm
SDQ
-
HOU
8h 46m
1 stop
JetBlue Logo
6:00 am - 1:10 pm
HOU
-
SDQ
6h 10m
1 stop
$811JetBlue
Sat, Mar 21 - Thu, Mar 26
JetBlue Logo
2:35 pm - 10:42 pm
SDQ
-
HOU
9h 07m
1 stop
JetBlue Logo
6:00 am - 1:10 pm
HOU
-
SDQ
6h 10m
1 stop
$858JetBlue
Fri, Feb 27 - Tue, Mar 3
WestJet Logo
3:50 pm - 3:03 pm
BGI
-
HOU
25h 13m
2 stops
WestJet Logo
5:19 pm - 2:53 pm
HOU
-
BGI
19h 34m
2 stops
$5,084WestJet
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$178
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 7% increase in price.
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 4 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.
7.9
DeltaOverall score based on 8126 reviews
7.9Comfort
8.1Boarding
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

10.0 ExcellentDr. Simon, Jan 2026
LAX - JFK
Read more Delta reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Very convenient considering that is a non-stop flight, but the Aeromexico still has old model planes, so the entertainment was very poor and the space for carry-on luggage was very limited.

Flight taking off must have been behind, because there was no pre-departure drink for first class like normal. Also, person in front of mine’s seat got stuck in the as far back as it normally goes position for the whole flight even during landing, flight attendant unable to fix it. Gate was not empty when we arrived, but that is MSP’s fault since was overdue for push back, not Delta’s, so had to sit on tarmac for a while and international flight so then still had to go through customs. Flight crew was excellent throughout though!

Delayed, toilets did not flush, pilot parked to far away from Gate

Check-in, boarding and the flight from Phoenix to Houston was quick and easy. The flight from Houston to Shreveport was delayed 5 hours. It was frustrating but I think United handled it the best they could.

The staff was hospitable and professional. The seat had a bit of wear. The winner shade was stuck 1/4 open. I received the best of both worlds. The morning sun was able to come in and blind the screen i was trying to use while at the same time it was too low to look out and enjoy the view. Rather embarrassing for a 1st class ticket.

In Liberia airport 5 min before our departure the airport was closed for takeoff for 30 min. Upon arrival to IAH we didn’t have any available gate and waited taxing another 40 min. As a result we arrived for 1+ h later. The walkway to the passport control in IAH is about 1-2 ml long. After the passport control you have to pass the security check again. Only 3 out of 16 checkpoints were open and the line was enormously long. As a result, even though we supposed to have 2.5 hrs gap in between the flights we missed our transfer. United rebooked us for the next available flight early morning and provided free hotel and meal vouchers through.

United is an incompetent airline. They parked the plane on the tarmac for an hour after arriving because they “didn’t have a gate available” it was actually some sort of lie because as we de planed there were approximately 9 open and manned and empty gates that we walked past. Many people on the flight missed connections for the hour long sit on the tarmac. Utterly baffling and incompetent behavior from United flight ops.

I boarded flight UA#1318 at Sacramento International Airport going back to Houston TX. The flight was scheduled at 5:10am. I was able to check in virtually using the United Airlines app. When I entered the airport, there was no one outside assisting with checked bags as it was for Delta Airlines. Immediately upon entering, there was a LONG, EXTREMELY LONG line to the kiosks to get boarding passes. I stand in line to get boarding passes then had to move to ANOTHER EXTREMELY LONG line to get my bags checked in. While standing in this line, we noticed an agent taking customers to 3 at a time to her station to check their bags in. Lucky for me, she called me back, checked my bags for me and I was on my way. I then encountered another long line at the TSA check and to avoid I ending up having to sign up for CLEAR to bypass it. So glad, I did.,...Both of my flights were great with no issues, butthe check in progress at Bush Airport was so much smoother. Check-in at SMF airport needs to be anaylzed and corrected. Do better United, I know you can....thanks

everything was pretty good. Houston airport is awful. Unnecessarily inefficient; people working there are rude. Badly run

Staff on board was excellent. Positive upbeat helpful- like it used to be.

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Crew was clearly not loving their jobs at any point of the entire trip. Flight back from Mexico, I asked if they had food for sale for the 2.5+hr flight and they did not have any. The business class trip to Mexico also had noted that the catering company forgot to load food. The last leg of trip back had a similarly unhappy crew, a broken toilet, and my seat was broken (reclining would not lock which made landing a crossfit like event). This was a bad week for AA.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

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.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Lower WiFi prices; allow us to see our flight on a map; more variety of drink choices.

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.

Loved that all flights were om time or early. Hated all the additional costs for a seat and luggage.

Our flight got rescheduled 48 hours later, the airline didn’t pay a penny for our expenses.

My baby was crying uncontrollably for the longest time and the entire crew was SO supportive, I’m so appreciative of them. Thank you so much for the support during an exhausting moment. We got very lucky.

Uncomfortable seats and tiny tray table. Expensive snacks. Flight was on time and crew was pleasant but take me back to Southwest!

Boarding and unboarding processes were pretty smooth. I gave a low score for Boarding because of how my flight was missing from all the boards at the airport, and when I checked the flight status on the Spirit website, it said it would be departing from Terminal E, gate D15. There are no "D" gates in terminal E.

The flight was on time and the crew was very professional and accommodating. When other airlines are canceling flights Spirit is still flying with on time flights. I have no complaints and will continue to choose Spirit when it is the best option for me.

Traveling to a place near Hobby?

Book flights to Hobby if you plan to visit one of these locations
Pearland
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