$98 Find Cheap Flights from Houston Hobby Airport to Caribbean Islands

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 Islands departing on 10/28. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Hobby to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$432
Santo Domingo
Santo Domingo1 stop$516
Montego Bay
Montego Bay1 stop$437
Oranjestad
Oranjestad2 stops$524
Nassau
Nassau1 stop$519
Simpson Bay
Simpson Bay2 stops$592
Kingston
Kingston1 stop$631
Providenciales
Providenciales1 stop$506
Port of Spain
Port of Spain2 stops$563
Bridgetown
Bridgetown1 stop$621
George Town
George Town2 stops$550
Willemstad
Willemstad2 stops$575
St. John's
St. John's2 stops$603
Puerto Plata
Puerto Plata2 stops$571
Punta Cana
Punta Cana2 stops$432
Santo Domingo
Santo Domingo1 stop$516
Montego Bay
Montego Bay1 stop$437
Oranjestad
Oranjestad2 stops$524
Nassau
Nassau1 stop$519
Simpson Bay
Simpson Bay2 stops$592
Kingston
Kingston1 stop$631
Providenciales
Providenciales1 stop$506
Port of Spain
Port of Spain2 stops$563
Bridgetown
Bridgetown1 stop$621
George Town
George Town2 stops$550
Willemstad
Willemstad2 stops$575
St. John's
St. John's2 stops$603
Puerto Plata
Puerto Plata2 stops$571

Book Cheap Hobby to Caribbean Islands Plane Tickets

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

Tue, Oct 21 - Sat, Oct 25
Delta Logo
10:13 am - 9:59 pmHOU-SJU
10h 46m1 stop
Delta Logo
7:15 am - 5:48 pmSJU-HOU
11h 33m1 stop
$215Delta
Find Deal
Tue, Sep 30 - Fri, Oct 3
American Airlines Logo
6:00 am - 6:14 pmHOU-SJU
11h 14m2 stops
American Airlines Logo
3:05 pm - 8:31 amSJU-HOU
18h 26m1 stop
$280American Airlines
Find Deal
Sun, Sep 28 - Sat, Oct 4
American Airlines Logo
8:32 pm - 2:15 pmHOU-SJU
16h 43m1 stop
American Airlines Logo
3:05 pm - 8:29 amSJU-HOU
18h 24m1 stop
$292American Airlines
Find Deal
Sun, Oct 5 - Thu, Oct 9
Southwest Logo
10:05 am - 8:40 pmHOU-SJU
9h 35m1 stop
Southwest Logo
1:05 pm - 9:35 pmSJU-HOU
9h 30m1 stop
$295Southwest
Find Deal
Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
6:00 am - 5:52 pmHOU-SJU
9h 52m2 stops
American Airlines Logo
7:15 am - 3:54 pmSJU-HOU
10h 39m1 stop
$315American Airlines
Find Deal
Sun, Oct 5 - Wed, Oct 8
American Airlines Logo
6:00 am - 2:15 pmHOU-SJU
7h 15m1 stop
American Airlines Logo
3:34 pm - 8:29 amSJU-HOU
17h 55m1 stop
$325American Airlines
Find Deal
Thu, Oct 16 - Thu, Oct 30
Southwest Logo
3:05 pm - 9:55 pmHOU-SJU
5h 50m1 stop
Southwest Logo
1:05 pm - 9:35 pmSJU-HOU
9h 30m1 stop
$340Southwest
Find Deal
Tue, Nov 4 - Sat, Nov 15
American Airlines Logo
6:00 am - 3:06 pmHOU-SJU
7h 06m1 stop
American Airlines Logo
7:15 am - 5:54 pmSJU-HOU
12h 39m1 stop
$350American Airlines
Find Deal
Thu, Oct 16 - Thu, Oct 30
Southwest Logo
11:30 am - 9:55 pmHOU-SJU
9h 25m2 stops
Southwest Logo
5:50 am - 4:40 pmSJU-HOU
11h 50m2 stops
$366Southwest
Find Deal
Sat, Nov 29 - Wed, Dec 3
Delta Logo
6:00 am - 4:34 pmHOU-MBJ
9h 34m1 stop
Delta Logo
5:59 pm - 9:44 amMBJ-HOU
16h 45m1 stop
$464Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Hobby to Caribbean Islands flights

Get data-powered insights and trends into flights from Hobby to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Houston Hobby Airport to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Houston Hobby Airport found in the last 72 hours was to Montego Bay, at $508 round-trip. The most popular route is from Houston Hobby Airport (HOU) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $886.

Can I save money by flying with a layover from Houston Hobby Airport to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $358, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Houston Hobby Airport to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Houston Hobby Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Houston Hobby Airport to Caribbean Islands is October, when tickets cost $280 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $480 and $387 respectively.

What’s the cheapest day of the week to fly from Houston Hobby Airport to Caribbean Islands?

The average price of all round-trip flights from Houston Hobby Airport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Houston Hobby Airport to Caribbean Islands, look for departures on Sundays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean Islands, Saturday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Houston Hobby Airport to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Houston Hobby Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Houston Hobby Airport to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$98
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Houston Hobby Airport to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

  • 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 Islands?

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

    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 from Houston Hobby Airport to Caribbean Islands with an airline and back 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 Islands?

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

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $247 on average. Morning departures are around 7% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $503.

  • How many flights are there between Houston Hobby Airport and Caribbean Islands per day?

    There is a maximum of 1 nonstop flight a day that takes off from Houston Hobby Airport and lands in Caribbean Islands, with an average flight time of 3h 10m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 1 flights.

Reviews of the top 5 airlines serving from Hobby to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Houston to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hobby to Caribbean Islands? 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 4242 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Plane was crowded and even when we hit altitude, the plane was hot, not enough air flow.

Flight was delayed and missed my connection Lufthansa didn’t respond.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

Overall it was good. I missed my connection but I was put on another flight.

Although the flight was delayed the crew and the flight itself were very good. Couldn't fault anything and after the disappointment of being abandoned in the US by BA it was a welcome relief to travel with United

Boarding experience was smooth. Flight attendants were friendly and helpful. Entertainment system on the Houston-Edmonton flight did not function for passengers on the left side of the aisle. On the bird's eye flight from Quito to Houston, they should not serve a meal. No one needs to eat after midnight and it is disturbing for those passengers trying to sleep.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

My suitcase was completed destroyed. The top part is broken and unusable now.

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Our bags took a long time to get unloaded once we landed.

My flight was delayed for several hours. Sitting at gate 16 for several hours, I got a text from Kayak the gate changed to 9 before it was announced. Very bad communication at each gate from American Airlines employees. I received 10 notifications of delay from Kayak. My vacation started off horrible! I will write to American Airlines corporate office also.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

Delayed flight that lead to a missed connection and a 5-hour trip became a 12-hour flight 🙄

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Great flight. No issues at all. I still think boarding could be more efficient but otherwise, a good experience.

Crew should be nicer and emphatic with customers. Same cookies as the past 20 years. Seat are ok and the plane was clean though it was delayed.

Spirit is low fare air line. Food also cost you. No free food.

Everyone was kind for the most part. I did travel with children and paid for seats and even then it was not as suitable. I tried calling their customer service prior to check in and I was told they couldn't help me because I didn't purchase my tickets with them.

I think the staff was nice. They took time to explain safety protocols. Boarding was great. They started early and our flight left a little early which was convenient. Having free games to play would have been better

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

Better than my las vagas experience, but still dissapointed with the airline support service.

Unfortunately, spirits crew had us boarding and parking the plane often, would wait long periods of time before allowing the people attending the flight on the plane to know what was going on this caused for my plane to not only get diverted but then canceled at an airport 2 hours away and basically stranded with charter buses MAYBE being hired. I was left with no choice but to stay overnight and use a comp room in Altantic City to then arrive home the next day. This trip was the first time seeing my partner since he joined the Air Force and this stressful ride caused unwarranted tears on what was supposed to be an east flight home. I understand weather is unpredictable but to have passengers deboard to then reboard an hour later to taxi on the runway for another hour to then basically leave an entire fight stranded. I waited almost 30 minutes at the airport and not one employee could tell me about a charter bus so I had to leave and make accommodations to stay overnight and get a ride home.

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

I will never fly with Spirit again. I was late getting through TSA after dealing with traffic and getting on the wrong shuttle. I got to the gate 2 minutes before the ticket said the gate closes and they agents were gone and doors were closed. They rescheduled my flight for 12 hours later and the agent had the nerve to tell me, “Be on time next time”. I was already upset from nothing going right for me that morning. I booked another flight through Alaska Airlines and they were very accommodating, nerer again Spirit Airlines!!!!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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