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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 5/15. 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
Thu 6/6
Thu 6/13

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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$433
Montego Bay
Montego Bay1 stop$486
Santo Domingo
Santo Domingo1 stop$495
Oranjestad
Oranjestad1 stop$641
Nassau
Nassau1 stop$483
Kingston
Kingston1 stop$741
Simpson Bay
Simpson Bay1 stop$555
Providenciales
Providenciales2 stops$585
Port of Spain
Port of Spain2 stops$671
Bridgetown
Bridgetown2 stops$713
George Town
George Town1 stop$578
Aguadilla
Aguadilla1 stop$333
Willemstad
Willemstad2 stops$721
St. John's
St. John's2 stops$749

Good to know

Low season

February

High season

June

Cheapest flight

$109
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 14% 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 14% 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 10810 reviews
8.6Crew
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

There was a group of school age passengers that were very loud and unruly with their chaperones were no where to be found.

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.

Flight was cancelled had to move to another gate late again no internet paid for the month and never can use it waste of money

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

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.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

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

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

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.

Book cheap flights from Houston to Caribbean

Recent round-trip flight deals

9/7Sat
1 stopDelta
10h 39mHOU-SJU
9/11Wed
1 stopDelta
8h 50mSJU-HOU
$274
6/12Wed
1 stopFrontier
10h 29mHOU-SJU
6/17Mon
1 stopFrontier
10h 01mSJU-HOU
$290
6/26Wed
1 stopFrontier
10h 29mHOU-SJU
6/27Thu
2 stopsFrontier
20h 50mSJU-HOU
$297
8/14Wed
1 stopDelta
10h 39mHOU-SJU
8/20Tue
1 stopDelta
11h 06mSJU-HOU
$329
9/3Tue
1 stopAmerican Airlines
8h 49mHOU-SJU
9/11Wed
2 stopsAmerican Airlines
8h 36mSJU-HOU
$384
8/28Wed
2 stopsAmerican Airlines
10h 40mHOU-SJU
9/1Sun
1 stopAmerican Airlines
9h 13mSJU-HOU
$419
6/13Thu
2 stopsBritish Airways
17h 12mHOU-GCM
6/17Mon
2 stopsBritish Airways
11h 13mGCM-HOU
$760
5/23Thu
2 stopsBritish Airways
19h 32mHOU-MBJ
5/27Mon
2 stopsBritish Airways
13h 20mMBJ-HOU
$1,315
6/3Mon
2 stopsWestJet
19h 49mHOU-NAS
6/10Mon
2 stopsWestJet
23h 24mNAS-HOU
$1,436
7/19Fri
2 stopsWestJet
23h 35mHOU-GCM
7/21Sun
2 stopsWestJet
25h 57mGCM-HOU
$1,473

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Recent one-way flight deals

5/15Wed
1 stopFrontier
6h 26mHOU-SJU
$109
5/13Mon
1 stopFrontier
16h 38mHOU-SJU
$113
6/3Mon
1 stopFrontier
7h 08mHOU-SJU
$145
5/13Mon
2 stopsAmerican Airlines
18h 13mHOU-SJU
$163
8/30Fri
1 stopAmerican Airlines
17h 16mHOU-SJU
$187
5/30Thu
2 stops
26h 55mHOU-SJU
$212
7/28Sun
1 stopDelta
16h 12mHOU-MBJ
$221
8/20Tue
1 stopDelta
15h 32mHOU-PUJ
$231
6/28Fri
1 stopSun Country Air
19h 44mHOU-SJU
$246
5/30Thu
3 stops
30h 10mHOU-SJU
$289

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Last minute flights from Hobby to Caribbean

Last minute flight, train and bus deals

5/10Fri
multi-stopFrontier
11h 46mHOU-SJU
5/15Wed
multi-stopFrontier
7h 05mSJU-HOU
$278
5/10Fri
multi-stopFrontier
13h 45mHOU-SJU
5/14Tue
multi-stopFrontier
15h 30mSJU-HOU
$285
5/10Fri
multi-stopAmerican Airlines
15h 13mHOU-SJU
5/13Mon
multi-stopAmerican Airlines
15h 56mSJU-HOU
$334
5/10Fri
multi-stopFrontier
11h 46mHOU-SJU
5/12Sun
multi-stopFrontier
17h 05mSJU-HOU
$338
5/8Wed
multi-stopFrontier
16h 43mHOU-SJU
5/12Sun
multi-stopFrontier
17h 05mSJU-HOU
$358
5/8Wed
multi-stopAmerican Airlines
11h 30mHOU-SJU
5/10Fri
multi-stopAmerican Airlines
10h 00mSJU-HOU
$489
5/8Wed
multi-stop
13h 40mHOU-SJU
5/11Sat
multi-stop
27h 54mSJU-HOU
$522
5/8Wed
multi-stop
13h 40mHOU-SJU
5/11Sat
multi-stop
27h 54mSJU-HOU
$533
5/11Sat
multi-stopDelta
7h 44mHOU-PUJ
5/15Wed
multi-stopDelta
10h 15mPUJ-HOU
$780
5/11Sat
multi-stopDelta
8h 44mHOU-PUJ
5/13Mon
multi-stopDelta
19h 21mPUJ-HOU
$810

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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: