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Find cheap flights from Houston Hobby Airport to Caribbean from $112

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 5/11. 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.
1 adult
0 bags
Sat 5/25
Sat 6/1

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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$357
Montego Bay
Montego Bay1 stop$466
Santo Domingo
Santo Domingo1 stop$284
Oranjestad
Oranjestad2 stops$639
Nassau
Nassau1 stop$463
Kingston
Kingston2 stops$643
Simpson Bay
Simpson Bay2 stops$559
Providenciales
Providenciales1 stop$632
Port of Spain
Port of Spain2 stops$776
Bridgetown
Bridgetown2 stops$825
George Town
George Town1 stop$603
Aguadilla
Aguadilla1 stop$398
Willemstad
Willemstad2 stops$556
St. John's
St. John's2 stops$794

Good to know

Low season

January

High season

June

Cheapest flight

$112
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 3% 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 verified KAYAK customer reviews.
8.0
DeltaOverall score based on 11004 reviews
7.5food
7.9comfort
8.0entertainment
8.6crew
8.2boarding
Airline reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

6.0 GoodDan, Apr 2024LGA - DEN
Read more about Delta reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

Trip was smooth bumpy from the wind but no issues at all the crew attendant was very pleasant and had great customer service

I liked everything about the flight. The service was excellent!

Delayed a day due to snow storm. Was upgraded. That kind of made up for significant delays from FLL to COS with no compensation or acknowledgement.

The Polaris experience is top notch. From departure lounge to arrival lounge. Everything was top notch. One of the best first class experience

The leg space between me and the seat in front of me was excellent.

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!

Missed the flight because of them and up geting a rental car

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

I arrived to the airport 2 hours before my American Airlines flight was scheduled to take off. I have TSA pre-check. The airport was crazy packed when I arrived. After momentarily standing in the pre-check line, the TSA agent said that I am not pre-check. Of course I said that I am because I entered my KTN number on all my traveling sites and programs. I had to get out of line and go back to the AA counter to discover that American Airlines did not add my KTN to my boarding pass. I had to call TSA to find out my number, then have AA enter it onto my boarding pass. The emblem would not load onto my boarding pass. By this time, I decided to use my Clear in order to get through TSA but the line was ridiculous long. By the time I made through TSA, I missed my 11:08am flight and was re-booked for the 5:30pm. This is after the AA employee told me I should have gotten to the airport early. AA use to be a dependable airline not I use them only if I have too.

Flight from SBP to DFW 1. They rerouted us through PHX 2. Delayed flight out of SBP for 3 hrs so we missed our connection Downgrade on rerouted flight. Back of the plane, center seats, didn't sit together 4. Return flight out of DFW same exact thing. Delayed, missed connection, Downgrade + they lost our luggage! A complete mess.

Do not eat the bagel! Otherwise, good albeit late, breakfast in first. Boarding downgrade only because flight was delayed due to plane change due to undisclosed problem with original aircraft. I did not use entertainment.

Was as expected. Good leg room on planes - much appreciated.

Fight crew was not very attentive and the bastions were gross!

I don’t think the flight attendants are happy. They do not seem to be friendly or welcoming.

Gossipy flight attendants talked the whole flight about bar hopping and dating.

Didn't like the 6 hour delay as it caused me to miss all of my connections. Still, I did get home safely 14 hours late but exhausted.

The crew was courteous and are very well prepared for the job.

Terrible as usual!!!! Very unprofessional and rude flight attendants! You get what you pay for! HORRIBLE

The text told me it was changed to Terminal E and Gate D5. But with no one on site to ask questions there was confusion on where to go as all the gates were E's. Then we took the skyline to the D area. We left to get something to eat. No announcement was made but my daughter happened to asked and they told her our gate was moved to D12. I will not fly Spirit again.

Unnecessary announcements through out flight. WiFi on plane is terrible and overpriced

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.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Houston to Caribbean

Recent round-trip flight deals

5/10Fri
1 stopFrontier
28h 47mHOU-SJU
5/12Sun
1 stopFrontier
17h 05mSJU-HOU
$189
5/10Fri
1 stopFrontier
28h 47mHOU-SJU
5/15Wed
1 stopFrontier
12h 23mSJU-HOU
$195
5/8Wed
1 stopAmerican Airlines
11h 30mHOU-SJU
5/10Fri
1 stopAmerican Airlines
12h 07mSJU-HOU
$224
5/6Mon
1 stopFrontier
16h 38mHOU-SJU
5/9Thu
1 stopFrontier
24h 30mSJU-HOU
$235
5/8Wed
1 stop
29h 30mHOU-SDQ
5/15Wed
1 stop
11h 21mSDQ-HOU
$284
5/8Wed
2 stops
17h 43mHOU-SDQ
5/15Wed
1 stop
11h 21mSDQ-HOU
$302
5/7Tue
2 stopsAmerican Airlines
9h 45mHOU-SJU
5/10Fri
1 stopAmerican Airlines
10h 00mSJU-HOU
$344
5/22Wed
1 stopDelta
9h 28mHOU-NAS
5/29Wed
1 stopDelta
8h 43mNAS-HOU
$463
10/14Mon
1 stopDelta
16h 18mHOU-MBJ
10/18Fri
1 stopDelta
17h 16mMBJ-HOU
$466
5/9Thu
2 stopsBritish Airways
11h 20mHOU-SDQ
5/15Wed
2 stopsBritish Airways
17h 32mSDQ-HOU
$817

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Recent one-way flight deals

5/11Sat
1 stopAmerican Airlines
7h 25mHOU-SJU
$112
5/6Mon
1 stopFrontier
16h 38mHOU-SJU
$121
5/1Wed
1 stopFrontier
16h 58mHOU-SJU
$122
4/29Mon
1 stopFrontier
13h 35mHOU-SJU
$133
6/3Mon
1 stopFrontier
7h 08mHOU-SJU
$145
5/21Tue
1 stopAmerican Airlines
15h 45mHOU-SJU
$187
7/28Sun
1 stopDelta
16h 12mHOU-MBJ
$211
5/21Tue
1 stopDelta
15h 37mHOU-NAS
$263
8/23Fri
2 stopsWestJet
46h 42mHOU-MBJ
$1,648
7/31Wed
2 stopsWestJet
23h 44mHOU-PUJ
$1,655

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Last minute flights from Hobby to Caribbean

Last minute flight, train and bus deals

4/29Mon
multi-stopFrontier
16h 38mHOU-SJU
5/12Sun
multi-stopFrontier
17h 05mSJU-HOU
$248
4/29Mon
multi-stopFrontier
13h 35mHOU-SJU
5/6Mon
multi-stopFrontier
13h 58mSJU-HOU
$256
4/29Mon
multi-stopFrontier
16h 38mHOU-SJU
5/5Sun
multi-stopFrontier
17h 05mSJU-HOU
$268
4/28Sun
multi-stopAmerican Airlines
9h 35mHOU-SJU
4/30Tue
multi-stopAmerican Airlines
9h 52mSJU-HOU
$674
4/25Thu
multi-stopAmerican Airlines
16h 49mHOU-SJU
4/29Mon
multi-stopAmerican Airlines
10h 10mSJU-HOU
$694
4/29Mon
multi-stopDelta
7h 40mHOU-PUJ
4/30Tue
multi-stopDelta
8h 23mPUJ-HOU
$735
4/26Fri
multi-stopDelta
17h 21mHOU-PUJ
5/4Sat
multi-stopDelta
10h 25mPUJ-HOU
$785
4/28Sun
multi-stop
18h 20mHOU-NAS
5/1Wed
multi-stop
7h 53mNAS-HOU
$922
4/28Sun
multi-stopWestJet
12h 34mHOU-MBJ
4/29Mon
multi-stopWestJet
23h 25mMBJ-HOU
$4,472
4/28Sun
multi-stopWestJet
12h 34mHOU-MBJ
4/29Mon
multi-stopWestJet
29h 39mMBJ-HOU
$4,491

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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: