$170 Find Cheap Flights from Caribbean Islands to Houston Hobby Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Hobby departing on 8/16. 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 Houston Hobby Airport

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean Islands to Hobby

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

jue., sep. 17 - mar., sep. 22
Southwest Logo
1:10 pm - 6:15 pm
NAS
-
HOU
6h 05m
1 stop
Southwest Logo
6:25 am - 12:15 pm
HOU
-
NAS
4h 50m
1 stop
$401Southwest
sáb., sep. 19 - mar., sep. 22
Southwest Logo
1:25 pm - 8:40 pm
NAS
-
HOU
8h 15m
1 stop
Southwest Logo
6:25 am - 12:15 pm
HOU
-
NAS
4h 50m
1 stop
$424Southwest
jue., sep. 17 - mar., sep. 22
Southwest Logo
1:10 pm - 9:20 pm
NAS
-
HOU
9h 10m
2 stops
Southwest Logo
6:25 am - 12:15 pm
HOU
-
NAS
4h 50m
1 stop
$432Southwest
mié., jul. 22 - mié., jul. 29
Southwest Logo
8:45 am - 7:10 pm
NAS
-
HOU
11h 25m
1 stop
Southwest Logo
10:25 am - 6:35 pm
HOU
-
NAS
7h 10m
1 stop
$460Southwest
mié., jul. 22 - mié., jul. 29
Southwest Logo
8:45 am - 7:10 pm
NAS
-
HOU
11h 25m
1 stop
Southwest Logo
10:25 am - 6:35 pm
HOU
-
NAS
7h 10m
2 stops
$464Southwest
jue., ago. 20 - dom., ago. 23
Delta Logo
2:59 pm - 10:05 pm
SJU
-
HOU
8h 06m
1 stop
Delta Logo
6:00 am - 4:38 pm
HOU
-
SJU
9h 38m
1 stop
$466Delta
mar., nov. 3 - dom., nov. 8
American Airlines Logo
4:02 pm - 11:57 pm
MBJ
-
HOU
8h 55m
1 stop
American Airlines Logo
6:00 am - 2:59 pm
HOU
-
MBJ
7h 59m
1 stop
$474American Airlines
sáb., sep. 12 - lun., sep. 14
American Airlines Logo
3:35 pm - 8:56 am
SJU
-
HOU
18h 21m
1 stop
American Airlines Logo
6:04 am - 2:45 pm
HOU
-
SJU
7h 41m
1 stop
$485American Airlines
vie., ago. 14 - dom., ago. 23
Delta Logo
2:59 pm - 10:05 pm
SJU
-
HOU
8h 06m
1 stop
Delta Logo
6:00 am - 4:38 pm
HOU
-
SJU
9h 38m
1 stop
$496Delta
mié., jul. 15 - dom., jul. 26
Multiple Airlines Logo
10:05 pm - 7:14 pm
POS
-
HOU
22h 09m
3 stops
Multiple Airlines Logo
6:10 pm - 12:15 am
HOU
-
POS
29h 05m
3 stops
$1,605Multiple Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$170
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 9% increase in price.
Flight from San Juan to Houston Hobby Airport

FAQs for booking Caribbean Islands to Houston Hobby Airport flights

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

    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 Caribbean Islands to Houston Hobby Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Houston Hobby Airport?

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

    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 Houston Hobby Airport with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Houston Hobby Airport?

    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 Houston Hobby Airport from 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 3 airlines serving from Caribbean Islands to Hobby

 
Need help choosing which airline to fly with from Caribbean Islands to Hobby? 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
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

4.0 OkayAnonymous, May 2026
MSY - HOU
Read more Southwest reviews

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

The seat was not comfortable. 1D. My back was sore all night and the next day.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

The flight was delayed, they didn’t even have water for the toilets or for drinks

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

The flight had a delay but I made it to my connection. Flight was smooth overall

The flight to Houston the agents were not very helpful

Horrible, absolutely horrible. The airline overbooked the flight, did NOT assign seats and boarding was a hot mess with lots of confused passengers. There was no "large plane" gate for us, the 500+ passengers were squeezed in a small hold room area, and multiple busses had to shuttle us to the other side of the airfield, where boarding of the plane, that was parked on the ramp, took place in rain. The old plane had a broken seat, that the technicians tried to fix - with no success - resulting in a 50min delay. The flight attendant with heart shaped earnings with German flag was screaming on the passengers without a reason, was extremely rude and entitled the entire flight. The food was junk. I hope I don't have to fly United ever again.

No screens or meal options. Freezing cold. Dirty seats. Left late.

It was terrible. sat on airplane 2 hours then flight was canceled. made to pick up bags and go through Panama immagration to rebook another flight. worst experice ever at a airport.

Good but airlines getting smaller. I didn't like the meal but the service was fine. Flight was fine and luggage arrived. So good.

Lounges are packed and very poor, food is really bad, for business class in an airline is well below expectations

Leave on time. We waited on the plane for hour hours and it was hot and smelly

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

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.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

Food is what you expect on a plane. Nothing gluten free. But that is expected. Drinks, apple juice, was fine. Seat, what I expected. Fine.

The flight took off an hour late which made the connection concerning

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

Traveling to a place near Hobby?

Book flights to Hobby if you plan to visit one of these locations
Pearland
Rosenberg
Stafford
Seabrook
West University Place
Freeport
La Marque
Nassau Bay

Everything you need to know for your flight to Hobby

Information on your arrival and departure airports