$150 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 7/7. 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, 0 bags

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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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 Cana1 stop$512
Santo Domingo
Santo Domingo1 stop$610
Montego Bay
Montego Bay2 stops$515
Oranjestad
Oranjestad1 stop$448
Nassau
Nassau1 stop$382
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$389
Providenciales
Providenciales2 stops$429
Port of Spain
Port of Spain2 stops$654
Bridgetown
Bridgetown2 stops$697
George Town
George Town1 stop$406
Willemstad
Willemstad2 stops$673
Puerto Plata
Puerto Plata2 stops$680
St. John's
St. John's2 stops$675
Punta Cana
Punta Cana1 stop$512
Santo Domingo
Santo Domingo1 stop$610
Montego Bay
Montego Bay2 stops$515
Oranjestad
Oranjestad1 stop$448
Nassau
Nassau1 stop$382
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$389
Providenciales
Providenciales2 stops$429
Port of Spain
Port of Spain2 stops$654
Bridgetown
Bridgetown2 stops$697
George Town
George Town1 stop$406
Willemstad
Willemstad2 stops$673
Puerto Plata
Puerto Plata2 stops$680
St. John's
St. John's2 stops$675

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

Wed, Aug 19 - Tue, Aug 25
Southwest Logo
2:45 pm - 10:00 pm
HOU
-
SJU
6h 15m
1 stop
Southwest Logo
1:20 pm - 7:50 pm
SJU
-
HOU
7h 30m
1 stop
$376Southwest
Sat, Aug 29 - Wed, Sep 2
Southwest Logo
6:40 am - 12:30 pm
HOU
-
NAS
4h 50m
1 stop
Southwest Logo
1:10 pm - 7:20 pm
NAS
-
HOU
7h 10m
1 stop
$382Southwest
Fri, Aug 7 - Sun, Aug 16
Southwest Logo
5:05 am - 2:05 pm
HOU
-
SXM
8h 00m
1 stop
Southwest Logo
3:05 pm - 11:15 pm
SXM
-
HOU
9h 10m
1 stop
$389Southwest
Sun, Aug 16 - Fri, Aug 21
Delta Logo
6:00 am - 1:42 pm
HOU
-
SJU
6h 42m
1 stop
Delta Logo
2:59 pm - 10:05 pm
SJU
-
HOU
8h 06m
1 stop
$466Delta
Sun, Jul 12 - Thu, Jul 16
American Airlines Logo
6:03 am - 11:50 pm
HOU
-
SJU
16h 47m
1 stop
American Airlines Logo
12:58 am - 3:44 pm
SJU
-
HOU
15h 46m
1 stop
$469American Airlines
Sun, Aug 23 - Sat, Aug 29
Delta Logo
6:00 am - 1:42 pm
HOU
-
SJU
6h 42m
1 stop
Delta Logo
7:00 am - 4:25 pm
SJU
-
HOU
10h 25m
1 stop
$471Delta
Sun, Aug 16 - Mon, Aug 24
Delta Logo
6:00 am - 1:42 pm
HOU
-
SJU
6h 42m
1 stop
Delta Logo
2:59 pm - 10:05 pm
SJU
-
HOU
8h 06m
1 stop
$476Delta
Fri, Aug 21 - Mon, Aug 24
American Airlines Logo
6:14 pm - 11:32 am
HOU
-
MBJ
17h 18m
2 stops
American Airlines Logo
2:52 pm - 9:03 am
MBJ
-
HOU
18h 11m
2 stops
$515American Airlines
Fri, Aug 21 - Mon, Aug 24
American Airlines Logo
6:14 pm - 11:32 am
HOU
-
MBJ
17h 18m
2 stops
American Airlines Logo
2:52 pm - 9:03 am
MBJ
-
HOU
18h 11m
2 stops
$540American Airlines
Fri, Jul 31 - Sat, Aug 22
American Airlines Logo
6:03 am - 4:14 pm
HOU
-
MBJ
10h 11m
1 stop
American Airlines Logo
12:47 pm - 9:02 am
MBJ
-
HOU
20h 15m
1 stop
$542American Airlines
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 5 days was to Montego Bay, at $503 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 5 days was $536.

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

The average price for all round-trip flights from Houston Hobby Airport to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $552 on average. Morning departures are around 1% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $580.

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 $451, 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 $82 (return) on average. On the other hand, the most expensive months are May and July, when the average cost of round-trip tickets is $1,083 and $973 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 Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean Islands, Thursday 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 7 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$150
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Houston Hobby Airport to Simpson Bay

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.

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.
7.9
SouthwestOverall score based on 4235 reviews
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

10.0 ExcellentAnonymous, Jun 2026
DEN - ORF
Read more Southwest reviews

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Boarded early, left early, arrived 40 mins early! A win win for me!

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

We had a delay, but thankfully I made it to my connection. Overall it went smooth

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

It's a long flight and I would have liked better snacks between lunch and the arrival meal. It's fine to have fruit and nuts but I really don't like ramen because it's salty junk soup. I'd suggest sandwiches. They're not expensive nor are they hard to store for a long flight. The FA's had a couple of big services and they were super busy preparing, executing and then cleaning up. Then they disappeared.

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

We had excellent customer service despite the chaos at George Bush airport in Houston!

It isvvery small flight. No leg room . No space to put my personal item at feet.

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

Another uncoordinated American experience. Always surprises me at DFW for them of all places. Have to take this flight as there are no other good time options. We knew from the start that something was wrong, but the pilot wouldn't tell us. I just watched my Kayak app grow the delay by 10 minutes as it went to 3.5 hours. They were uncoordinated with maintenance (as maintenance, when finally arriving, knew within 15 minutes the plane wasn't going. No 'sorry' or 'this is what is going on' comment. The pilot seemed unfazed / didn't care about the process we were going through.

The seats. The seat in front of me was awful and when the guy sat down, it flew back and hit my head when I was putting my backpack under the seat, It didn't make for a pleasant experience,

The flight back to Dallas was delayed, which has happened to me several times with American Airlines. There was no announcement, no update sent out, no compensation offered for the inconvenience.

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

The flight from Dallas to Tokyo was not on Japan Airlines. It was on American Airlines. Very disappointed that we did not fly on Japan Airlines. Will not be using you liars again. I’ll just book direct from the airline next time. Wish you could make this right and has us fly on Japan Air when heading back home to the US.

They made nearly everyone check their bag because the overhead bins are way too small. Extremely inconvenient

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

Movies on my phone are great. It would be nice to have a gluten free snack option.

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports