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Find cheap flights from Houston Hobby Airport to Caribbean from $109

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 departing on 5/1. 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
0 bags
Do 4/18
Do 4/25

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$269
Montego Bay
Montego Bay2 stops$325
Santo Domingo
Santo Domingo2 stops$620
Nassau
Nassau1 stop$425
Oranjestad
Oranjestad1 stop$556
Kingston
Kingston2 stops$666
Providenciales
Providenciales1 stop$582
Simpson Bay
Simpson Bay1 stop$595
Port of Spain
Port of Spain2 stops$576
Bridgetown
Bridgetown2 stops$644
George Town
George Town2 stops$583
Aguadilla
Aguadilla1 stop$784
Willemstad
Willemstad2 stops$556
St. John's
St. John's2 stops$754
Port Au Prince
Port Au Prince2 stops$1,102

Good to know

Low season

January

High season

June

Cheapest flight

$109
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Houston Hobby Airport to San Juan

FAQs - booking Caribbean flights

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

    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.

  • 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?

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

    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 Caribbean with an airline and back to Houston Hobby Airport 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?

    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 Caribbean from Houston Hobby Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 17% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Hobby to Caribbean

Need help choosing which airline to fly with from Hobby to Caribbean? 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 KAYAK reviews.
8.0
DeltaOverall score based on 11551 reviews
81overall
79comfort
82boarding
81entertainment
75food
86crew
Airline reviews

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Read more about Delta

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

Please see my lengthy description on MSP to Atlanta survey. Tailbone is killing me from old hard seats. Seat would not recline and were not near exit row. Entertainment did not work properly and couldn’t use. No audio and touch screen failed. 3 plus hours of discomfort in narrower seats than previous flight not in comfort plus. Very dissatisfied and deserve comfort plus charges refunds, at the very least, for both my wife and I. The plane needs to be retired. Please feel free to contact me directly for further details.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

It wasn't really their fault it was the horrible winds and we just got unlucky.

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

The helpful attitude of the staff, and being a wheelchair passenger everyone was helpful and understanding. The trip was made comfortable by the upgraded seat which was given without my request, that was a great surprise. Thank you Delta.

Over two hours wait to get wheelchair assistance from arrival to the departure gate for LA was unreasonable even though there appreared to be heavy demand.

The seats were uncomfortable. The flight was almost 9 hours and they didn’t serve lunch

Got automatically assigned a middle seat, unless I fork out extra money for seat assigment.

The crew was nice but the people going to Orange County are so entitled. Everyone thinks everything is suppose for be perfect for them. Tough crowd.

Flight canceled due to weather. Rescheduled flight canceled due to maintenance. I’m stuck!

Cramped and uncomfortable seats. Not enough room for 6’2” person such as myself.

There was either a baby who pooped themself in the seat in front of me or someone who kept farting. It smelled like human fecal matter for the last hour of the flight.

Apparently the WiFi you buy on on one flight doesn't carry on with connecting flights.

It was ok until we got to DC and I wanted to use my United Club pass and the snobbish receptionist said that they don’t take one pass. It took me everything itch of patience not to tell her off

Nothing went smooth. From being threatened to pay $400 for omitting my middle name by agents in India or somewhere. In addition, I couldn't get an answer on how much a third bag would cost despite numerous calls to Lufthansa. Then I couldn't check in online because they wanted evidence of residency. I told them I have dual citizenship but that didn't help. Last but not least, my luggage didn't make it to my destination. I had Christmas presents that didn't get to family members on time. I also had to wait the entire day to have it delivered. I have never had such a bad experience with an airline. This is how you loose customers

My previous flight was late and did not connect properly. The gate was closed and I missed this flight.

The flight was 6 hr late and then they blamed it on the weather. All of the other planes were coming and going fine.

Overall okay. Ipgrades ate worthless anymore. Wish I’d not been so loyal To them for so many years. Platinum many years. Gold for life. Usually 20th-30th on upgrade list.

Well, flight times cause some wait, but there were not times available and we understood. I didn't check any luggage, because it has become too expensive. I was able to add any extra items to my co-travellers check bags. [Luckily, this trip wasn't international.] Last, I hadn't flown AA domestically for a while, but partners and coworkers had warned me in advance that not all planes have monitors at every seat. Luckily, I was mostly prepared to use the in-flight entertainment and happy I was. The great: AA staff is always kind and comfort is way better than the budget airlines that I sometimes have to fly. I know my points and vouchers all expired over the last couple of years, but I still enjoy AA when I do fly with them. I also appreciate all of the locations we can go directly from pur home airport. Since we are traveling more now, I hope to take advantage.

Our gate number was changed but nobody alerted us until we tried to board the wrong flight then they told us almost missed another flight. Very bad service.

The flight attended didn't ask one everyone in our party if they wanted a drink or snack. The one attended appeared to hate her job which is the one that attended to us.

Flight was delayed, I tried to leave 2days earlier was told to report to airport for standby only to be turned away after paying for an Uber both way from Little Elm TX.

Ground crew forced me to double pay for infant international charges, when I complained about this and told them, with proof, I already paid they threaten to not allow me on the plane because I was “being rude”. Horrible ground management, horrible airline.

Flight was changed last min. Had a screaming infant a row in front of me and a parent who did nothing to calm the child.

Flight was delayed over an hour due to flight crew issues, making difficult flight connection

Cancelled my flight last minute and had to end up driving to Texas from Atlanta last minute. I’m going to miss another day of work, drive back to Atlanta , in my own car and spirit doesn’t want to refund the money. First time I tried flying anyone else but delta and I get ripped off . And I had. To pay for seats for a flight that didn’t happen. Usually you could say you get what you pay for but in this case, didn’t get anything and paid for everything never flying spirit again, or even attempting it or thinking about it.

Flight from Tampa to Houston was canceled. SPIRIT rebooked me and they double booked my seat. Conclusion I COULD NOT TRAVEL TO HOUSTON. I MISSED MY GRANDDAUGHTER BIRTHDAY. I would not recommend this company. I will file a complaint. I will never consider SPIRIT as an airline . It’s a faker.

My flight was cancelled and I am stranded in another state

Had to board plan 2x due to lack of security check after 1st boarding

Bad weather is one thing but repeatedly changing gates AND terminals after several hours of delays was horrible. Additionally after the long delays, gate agents were delaying us evening further by being overly picky with personal item bag sizes. Get a grip.

Horrendous. Wish they would have just shot me in the leg instead.

Spirit cancels my flight and I have been stuck here at the airline since March 3rd 2pm and still here everything is close they didn’t accommodate me with a room or nothing they rebooked my flight for 7:25pm to New Orleans then from New Orleans to Fort Lauderdale I Wang Arrive Homw Until The 5th of March I am missing work I hav e kids to get home to and I am currently stuck with no food nowhere to stay no renter cause everything close I spent all my money and I’m very disappointed trying to get home I’m very very mad frustrated and very disappointed

Horrible. Delay after delay. People yelling and making obseen gestures!

It would have been no e to have the option of a mid day flight and not super early or super late in the day.

My experience was better than expected. What I did find not so great was the seats. Very little room, they did not recline and the tray table was the size of a post card. There was no food to try, just standard snacks that you had to pay for and I don’t know of any entertainment. I would fly again even though everything was an upcharge. Flight was on time with little disturbance

There was no wifi, there was no usb charger on the planes Frontier lowered the weight limit on suitcases from 50 to 40 pounds Frontier now charges for a seat...really? If i don't pay for a basic seat, do i stand the whole flight? Frontier now charges for the carry on, just like for the checked suitcase The bundle pricing is way over priced.

I am HIGHLY unhappy with the amount of money I spent on the flight. Paid in advance only to find the flight at a discount price a week or so before the flight. I will not fly frontier again and have bad mouthed your business since to anyone I have spoken with about flying (which has been many a people). Crew was mediocre and instead of moving me to a spot where I could gain some leg room they sat their flight attendant there. Won’t be flying frontier in the future.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Plane was clean but they do not allow bag drop until 1 hour before flight. Just encouraging late fees and other issues. The worst I have experienced. Total hostage situation, pay or you miss your flight.

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.

Well, I didn’t have food! So NA wasn’t an option. I’ll be back!

Bought seats on the flight and they were supposed to be 2 and a jumpseat. Plane clearly changed and it was a regular 3 seat row. Asked for a refund and was denied. If I wanted to sit next to someone else I wouldn't have bought the seats..

I dunno. Depressing, uncomfortable (I’m poor), but on time and efficient.

Everything was good, and most importantly on time. They have been extremely tardy in some of my flights

First time flying with Frontier . From buying tickets ,getting boarding pass and boarding plane was super easy. Definitely would fly again with Frontier .

Book cheap flights from Houston to Caribbean

Recent round-trip flight deals

4/12Fr
1 stopFrontier
21h 49mHOU-SJU
4/17Mi
1 stopFrontier
8h 35mSJU-HOU
$222
4/17Mi
1 stop
28h 41mHOU-SJU
4/24Mi
1 stop
8h 35mSJU-HOU
$224
4/15Mo
1 stopFrontier
16h 38mHOU-SJU
4/22Mo
1 stopFrontier
13h 58mSJU-HOU
$239
5/7Di
1 stopDelta
7h 43mHOU-SJU
5/14Di
1 stopDelta
7h 27mSJU-HOU
$274
5/8Mi
1 stopDelta
7h 43mHOU-SJU
5/14Di
1 stopDelta
7h 27mSJU-HOU
$369
4/30Di
2 stopsAmerican Airlines
9h 35mHOU-SJU
5/6Mo
1 stopAmerican Airlines
10h 00mSJU-HOU
$442
5/15Mi
1 stopAmerican Airlines
9h 23mHOU-SJU
5/18Sa
1 stopAmerican Airlines
10h 00mSJU-HOU
$464
4/7So
2 stopsRoyal Air Maroc
10h 10mHOU-PUJ
4/16Di
2 stopsRoyal Air Maroc
10h 19mPUJ-HOU
$697
6/25Di
2 stopsBritish Airways
10h 49mHOU-MBJ
7/5Fr
2 stopsBritish Airways
19h 36mMBJ-HOU
$786
3/31So
2 stopsBritish Airways
21h 20mHOU-PUJ
4/4Do
2 stopsBritish Airways
12h 31mPUJ-HOU
$1,016

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Recent one-way flight deals

5/1Mi
1 stop
28h 41mHOU-SJU
$109
4/15Mo
1 stopFrontier
13h 35mHOU-SJU
$120
4/19Fr
1 stopFrontier
16h 28mHOU-SJU
$121
5/6Mo
1 stopFrontier
13h 35mHOU-SJU
$123
5/8Mi
2 stops
25h 16mHOU-SJU
$136
4/24Mi
1 stopDelta
9h 20mHOU-SJU
$187
7/28So
1 stopDelta
16h 24mHOU-MBJ
$221
4/9Di
1 stopAmerican Airlines
16h 49mHOU-SJU
$232
4/28So
1 stopAmerican Airlines
7h 14mHOU-SJU
$239
6/21Fr
2 stopsWestJet
20h 18mHOU-NAS
$1,763

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Last minute flights from Hobby to Caribbean

Last minute flight, train and bus deals

3/20Mi
multi-stopFrontier
25h 20mHOU-PUJ
3/25Mo
multi-stopFrontier
27h 01mPUJ-HOU
$480
3/23Sa
multi-stopAmerican Airlines
10h 03mHOU-SJU
3/30Sa
multi-stopAmerican Airlines
10h 14mSJU-HOU
$664
3/22Fr
multi-stopAmerican Airlines
16h 30mHOU-SJU
3/26Di
multi-stopAmerican Airlines
11h 05mSJU-HOU
$699
3/22Fr
multi-stopDelta
10h 41mHOU-SJU
3/26Di
multi-stopDelta
9h 01mSJU-HOU
$714
3/20Mi
multi-stopDelta
6h 35mHOU-PUJ
3/25Mo
multi-stopDelta
18h 09mPUJ-HOU
$740
3/21Do
multi-stopDelta
8h 47mHOU-MBJ
3/26Di
multi-stopDelta
8h 08mMBJ-HOU
$743
3/20Mi
multi-stopAmerican Airlines
10h 11mHOU-PUJ
3/25Mo
multi-stopAmerican Airlines
10h 36mPUJ-HOU
$743
3/21Do
multi-stopAmerican Airlines
6h 50mHOU-SJU
3/25Mo
multi-stopAmerican Airlines
19h 21mSJU-HOU
$754
3/19Di
multi-stopDelta
8h 47mHOU-MBJ
3/26Di
multi-stopDelta
15h 31mMBJ-HOU
$766
3/20Mi
multi-stopWestJet
31h 10mHOU-SXM
3/29Fr
multi-stopWestJet
25h 13mSXM-HOU
$3,978

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Houston Hobby Airport - Caribbean Flights

Departure:

Houston Hobby Airport (HOU)United States

Return flight deals:

Caribbean - Houston Hobby Airport

Cabin classes: