$83 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 8/25. 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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Caribbean Islands.
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Flights Deals

Best Caribbean Islands Flight Deals from Hobby

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$335
Santo Domingo
Santo Domingo2 stops$519
Montego Bay
Montego Bay2 stops$345
Oranjestad
Oranjestad2 stops$560
Nassau
Nassau1 stop$512
Kingston
Kingston1 stop$601
Simpson Bay
Simpson Bay2 stops$617
Providenciales
Providenciales2 stops$493
Port of Spain
Port of Spain2 stops$583
Bridgetown
Bridgetown2 stops$626
George Town
George Town1 stop$538
Willemstad
Willemstad2 stops$575
St. John's
St. John's2 stops$643
Puerto Plata
Puerto Plata2 stops$529
Punta Cana
Punta Cana1 stop$335
Santo Domingo
Santo Domingo2 stops$519
Montego Bay
Montego Bay2 stops$345
Oranjestad
Oranjestad2 stops$560
Nassau
Nassau1 stop$512
Kingston
Kingston1 stop$601
Simpson Bay
Simpson Bay2 stops$617
Providenciales
Providenciales2 stops$493
Port of Spain
Port of Spain2 stops$583
Bridgetown
Bridgetown2 stops$626
George Town
George Town1 stop$538
Willemstad
Willemstad2 stops$575
St. John's
St. John's2 stops$643
Puerto Plata
Puerto Plata2 stops$529

Cheap Flights from Hobby to Caribbean Islands

 
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 - Tue, Oct 28
Southwest Logo
4:55 pm - 11:50 pmHOU-SJU
5h 55m1 stop
Southwest Logo
7:40 am - 8:15 pmSJU-HOU
13h 35m2 stops
$165Southwest
Find Deal
Sun, Aug 31 - Sat, Sep 6
Delta Logo
10:22 am - 10:07 pmHOU-SJU
10h 45m1 stop
Delta Logo
7:30 am - 5:39 pmSJU-HOU
11h 09m1 stop
$215Delta
Find Deal
Fri, Sep 26 - Sat, Oct 4
Delta Logo
6:00 am - 4:08 pmHOU-SJU
9h 08m1 stop
Delta Logo
2:28 pm - 9:40 pmSJU-HOU
8h 12m1 stop
$255Delta
Find Deal
Fri, Aug 22 - Thu, Aug 28
Southwest Logo
7:55 am - 8:45 pmHOU-SJU
11h 50m1 stop
Southwest Logo
11:10 am - 8:15 pmSJU-HOU
10h 05m2 stops
$270Southwest
Find Deal
Tue, Sep 16 - Sat, Sep 20
Southwest Logo
7:05 am - 5:25 pmHOU-SJU
9h 20m2 stops
Southwest Logo
5:00 am - 1:25 pmSJU-HOU
9h 25m2 stops
$280Southwest
Find Deal
Mon, Sep 1 - Fri, Sep 12
American Airlines Logo
8:25 pm - 2:25 pmHOU-SJU
17h 00m1 stop
American Airlines Logo
3:05 pm - 8:34 amSJU-HOU
18h 29m1 stop
$294American Airlines
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Mon, Sep 22 - Wed, Oct 1
Delta Logo
6:00 am - 1:23 pmHOU-SJU
6h 23m1 stop
Delta Logo
2:28 pm - 9:40 pmSJU-HOU
8h 12m1 stop
$295Delta
Find Deal
Mon, Jul 14 - Wed, Jul 16
American Airlines Logo
8:23 pm - 5:06 amHOU-SJU
7h 43m1 stop
American Airlines Logo
12:59 am - 9:40 amSJU-HOU
9h 41m1 stop
$335American Airlines
Find Deal
Mon, Jul 14 - Sat, Jul 19
WestJet Logo
6:00 am - 12:45 pmHOU-GCM
30h 45m2 stops
WestJet Logo
1:45 pm - 5:55 pmGCM-HOU
28h 10m2 stops
$1,515WestJet
Find Deal
Sat, Aug 9 - Tue, Aug 12
WestJet Logo
5:00 pm - 10:23 amHOU-NAS
16h 23m2 stops
WestJet Logo
11:15 am - 10:31 pmNAS-HOU
12h 16m2 stops
$1,560WestJet
Find Deal
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Houston Hobby Airport to Caribbean Islands.

The cheapest ticket to Caribbean Islands from Houston Hobby Airport found in the last 72 hours was to San Juan, at $506 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 $506.

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 $388, 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 September, when tickets cost $264 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $480 and $378 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 Saturdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Caribbean Islands, Friday 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 5 weeks before departure.


Good to know

Low seasonSeptember
High seasonJuly
Cheapest flight$83
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 6% 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 $254 on average. Morning departures are around 3% 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 $515.

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 4278 reviews
8.6Crew
7.6Entertainment
8.2Boarding
7.1Food
8.0Comfort
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

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.

We boarded but then sat there waiting on some missed connection people to get on so we sat for about 15 minutes for that. Then we sat again because the passenger manifest was wrong and they had to figure it out before we could leave. That took about another 20 minutes or so. The crew was working hard to figure it out so it’s not their fault. It ended up being a system glitch where someone was upgraded to first class while another person was also in the same seat and it just created a mess that took a little while to figure out. They literally went to every person on the plane asking their names to see who was sitting in the wrong seat. I also hate the entertainment that must be watched on your phone or tablet. Just give us setback screens. It’s so much better. Almost every Delta flight has this now and it is so nice to have them. The crew did a great job. I have no complaints from them. They were very hard working, even with the mishap and a disgruntled passenger.

My priority checked bag was not loaded on the flight. I had to sit in baggage claim in Las Vegas for 2 1/2 hours waiting for the next flight. All baggage staff were very helpful, tracking showed it as scanned for loading. Nobody told me why it wasn't on my flight.

All male crew was just too woke for me. I felt like a sardine. I will never take a window seat or the rearmost seat again. I booked early and did not pay for seat selection and that was a mistake. The security at IAH was atrocious. I was violated and radiated as I was in a hurry to connect to my other flight. I may have lost items under the seat in front of me that I couldn't see nor bend over to look.

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

In general ok, my only issue is that they had no hot items for purchase. I had very little time in my connection due to baggage/customs/TSA, thag I barely even had a chance for a stop at the washroom and buy water, to make it to my gate when they started boarding. I had nothing to eat because the trip started early, so I was ready to purchase, and they had nothing except for dry items like snacks. I had to purchase a mediocre, overpriced cheese and fruit board, instead of at least a pizza or sliders that I was planning on getting. Other than that, it was fine. But that’s typical Air Canada, to not have enough.

How badly can you screw up baggage claim? We were told to go to baggage claim too for our bags from this flight. Another flights bags were there. They finished up. More bags from a different flight arrived. Our bags did not Finally the baggage claim belt stopped working and and are flight was still listed on the arrivals for that baggage claim 2. And then nothing It turns out that they had been delivered not only the United baggage claim but far away on a Delta baggage claim No I never told us. It was only the people looking around who had been on the flight But I’m sure there was plenty of time for the employees to raffle through the bags and steal whatever they wanted

Long wait before take off without an update for 20 minutes. Flight was good otherwise.

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

At the beginning of the flight there was some turbulence and the announcement was made that there would be no beverage service. The turbulence only last about 5 minutes then it was smooth sailing. I noticed that first class got their service, but the rest of us did not.

Update departure times in a more timely manner. We are not boarding on time if the plane isn’t arriving until after our scheduled departure time.

Update.us on flight information in a more timely manner. Don’t say we are boarding on time ten minutes before the boarding time when the aircraft isn’t arriving for another forty minutes.

Took off on time and successfully avoided weather that looked to be a problem along the way

I liked everything. Except that my neck was hurting on the seat. I couldn't sleep.

We were delayed Al ost / hours after boarding so that maintenance had to add oil to the engines. Then the oil they grabbed had been left out in the Dallas record cold and was frozen. They had to go back to the hanger and grab some that was not frozen.

They changed my seat from one that I had paid for as an upgrade to a regular seat at the last minute.

Flight was empty so had a whole row to myself. Still had to wait to get the bag due to the negligence at Palm Springs departure.

Everything was on time, we arrived early, everything worked well.

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!!!!

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

The flight was on time. The seats are very narrow.

Unclear pricing; ended up being charged an extra $52 just to get onboard

Seats are poor. They do not lean back. They do not even have pockets on the back, making it impossible to store a phone or a coke bottle. If you opt for basic economy cheap seats, they stick you always in the middle or window seat, even though there are unoccupied seats on the aisle. And then there is the nickel and diming. No carry-ons. And checking your carry-on is $70. At the end there is no price advantage but there is plenty of aggravation.

Flight crew was great. Spirit leaves a lot to be desired in terms of comfort.

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