HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$108+ Cheap flights from Hobby (HOU) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hobby to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Hobby to Caribbean Islands

Cheapest flights from Hobby to Caribbean Islands
Explore the most affordable flight options available from Hobby to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This American Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:44 amHOU - SJU
1 stop7h 00mAmerican Airlines
Tue 12/167:00 amSJU - HOU
1 stop15h 18mAmerican Airlines
Deal found 11/12$280
This American Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:44 amHOU - SJU
1 stop7h 00mAmerican Airlines
Sat 12/136:54 amSJU - HOU
1 stop15h 24mAmerican Airlines
Deal found 11/11$305
This American Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:08 amHOU - SJU
1 stop9h 17mAmerican Airlines
Thu 12/113:45 pmSJU - HOU
1 stop10h 13mAmerican Airlines
Deal found 11/11$325
This Delta deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/202:32 pmHOU - SJU
1 stop6h 41mDelta
Thu 12/41:55 pmSJU - HOU
1 stop10h 53mDelta
Deal found 11/12$334
This Southwest deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/81:35 pmHOU - SJU
2 stops9h 00mSouthwest
Thu 12/113:55 pmSJU - HOU
1 stop7h 00mSouthwest
Deal found 11/11$370
This Southwest deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:50 pmHOU - SJU
1 stop9h 45mSouthwest
Tue 12/165:45 amSJU - HOU
1 stop10h 50mSouthwest
Deal found 11/12$395
This Southwest deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/121:55 pmHOU - SJU
1 stop6h 25mSouthwest
Tue 12/1611:20 amSJU - HOU
1 stop9h 40mSouthwest
Deal found 11/12$405
This American Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2412:09 pmHOU - MBJ
1 stop23h 43mAmerican Airlines
Sun 12/286:00 pmMBJ - HOU
1 stop15h 32mAmerican Airlines
Deal found 11/12$405
This Southwest deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:45 pmHOU - MBJ
2 stops18h 10mSouthwest
Fri 12/121:00 pmMBJ - HOU
2 stops9h 35mSouthwest
Deal found 11/11$409
This American Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:44 amHOU - SJU
1 stop7h 00mAmerican Airlines
Thu 12/113:45 pmSJU - HOU
1 stop10h 13mAmerican Airlines
Deal found 11/12$410
This Southwest deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:30 amHOU - SJU
2 stops9h 05mSouthwest
Mon 12/89:40 amSJU - HOU
1 stop11h 55mSouthwest
Deal found 11/11$415
This American Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/145:44 amHOU - MBJ
1 stop8h 11mAmerican Airlines
Sat 12/276:00 pmMBJ - HOU
1 stop15h 32mAmerican Airlines
Deal found 11/12$419

Cheap flight deals from Hobby to Caribbean Islands

Keep the following information in mind while searching for Hobby to Caribbean Islands flight deals. Data was last updated November 13, 2025.

Round-trip from

$206
(Delta)

One-way from

$108
(Delta)

Popular in

December

Cheapest in

April

Average price

$465
From Houston Hobby to Caribbean Islands
Search Deals
One-way flight from Houston Hobby to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hobby to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 13, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to Caribbean Islands that are best for you.

Fly from

Hobby

Fly to

Caribbean Islands

Route

Depart

Return

Price

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sat 1/17

10:50 am-11:00 pm

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Fri 1/23

2:35 pm-7:40 pm

1 stop7h 05m

$290

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Fri 1/16

11:00 am-10:25 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:10 am-7:40 pm

2 stops15h 30m

$370

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 2/1

10:00 am-10:15 pm

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Thu 2/12

7:00 am-3:45 pm

2 stops10h 45m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 12/11

1:25 pm-12:35 am

2 stops9h 10m

San Juan Luis Munoz Marin Intl

Thu 12/18

3:30 pm-11:10 pm

2 stops9h 40m

$395

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sat 12/6

5:44 am-4:21 pm

2 stops9h 37m

Montego Bay Sangster Intl

Thu 12/11

3:57 pm-11:58 pm

1 stop9h 01m

$421

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Wed 12/10

6:35 pm-12:50 pm

2 stops17h 15m

Montego Bay Sangster Intl

Fri 12/12

1:00 pm-9:35 pm

2 stops9h 35m

$434

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sat 1/3

5:40 am-5:00 pm

1 stop10h 20m

Montego Bay Sangster Intl

Sat 1/10

4:29 pm-10:05 am

1 stop18h 36m

$436

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sat 1/24

11:00 am-5:10 pm

Nonstop4h 10m

San Juan Luis Munoz Marin Intl

Mon 1/26

5:40 am-11:55 am

1 stop8h 15m

$436

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Tue 12/2

6:00 am-4:33 pm

1 stop9h 33m

Montego Bay Sangster Intl

Wed 12/10

3:38 pm-10:48 pm

1 stop8h 10m

$439

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Wed 12/3

6:00 am-1:04 pm

1 stop6h 04m

Montego Bay Sangster Intl

Wed 12/10

5:58 pm-9:34 am

1 stop16h 36m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Hobby to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Hobby with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Houston Hobby Airport to Caribbean Islands

What is the cheapest month to book a flight from Houston Hobby Airport to Caribbean Islands?

Currently, April is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean Islands (average of $93). Flying from Houston Hobby Airport to Caribbean Islands in November is currently the most expensive (average of $174). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HOU to EPX?

Find hourly flight availability from Hobby to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

It’s typically best to fly out from Houston Hobby Airport to Caribbean Islands in the evening. Doing so could potentially save you 33% on the flight price compared to flying in the afternoon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Hobby to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Houston Hobby Airport to Caribbean Islands flight should consider departing on Monday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated November 13, 2025.
Read through reviews of airlines operating flights from Houston Hobby Airport to Caribbean Islands, such as Southwest, Delta, and United Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,139 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Hobby to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Houston Hobby Airport to Caribbean Islands?

    For as low as $439, Southwest can have you in Caribbean Islands from Houston Hobby Airport in 9h 33m. Houston Hobby Airport and Caribbean Islands are separated by a distance of 1335 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Houston Hobby Airport to Caribbean Islands one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $108. Users have also found prices from $161 and $219 on American Airlines and Southwest, respectively.

  • What are the most popular routes from Houston Hobby Airport to Caribbean Islands?

    The most popular flight routes from Houston Hobby Airport to Caribbean Islands are Houston Hobby - San Juan Luis Munoz Marin Intl, Houston Hobby - Punta Cana and Houston Hobby - Montego Bay Sangster Intl.

  • Can I find deals for flights from Hobby to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Hobby to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hobby to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hobby to Caribbean Islands.

  • Can I find deals for business class flights from Hobby to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Hobby to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Houston Hobby Airport to Caribbean Islands?

    Currently, April is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean Islands (average of $93). Flying from Houston Hobby Airport to Caribbean Islands in November is currently the most expensive (average of $174). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Hobby to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Hobby to LaGuardia flights
Hobby to Newark flights
Hobby to John F Kennedy Intl flights
George Bush Intcntl to Cancún flights
George Bush Intcntl to LaGuardia flights
George Bush Intcntl to John F Kennedy Intl flights
George Bush Intcntl to Newark flights
Hobby to Denver flights
Hobby to Las Vegas flights
Hobby to Cancún flights
Hobby to Mexico City flights
Hobby to Seattle flights
George Bush Intcntl to Denver flights
George Bush Intcntl to Las Vegas flights
Hobby to Los Angeles flights
George Bush Intcntl to Seattle flights
George Bush Intcntl to Mexico City flights
George Bush Intcntl to Los Angeles flights
Hobby to Reagan-National flights
Hobby to Baltimore flights
Hobby to Orlando flights
Hobby to Atlanta flights
Hobby to Midway flights
Hobby to Dulles Intl flights
Hobby to Cozumel flights
Hobby to O'Hare Intl flights
Hobby to Sky Harbor Intl flights
George Bush Intcntl to Cozumel flights
Hobby to Dallas/Fort Worth flights
Hobby to Ontario flights
Hobby to San Francisco flights
George Bush Intcntl to Ontario flights
Hobby to Nashville flights
George Bush Intcntl to Sky Harbor Intl flights
George Bush Intcntl to Orlando flights
George Bush Intcntl to Dallas/Fort Worth flights
Hobby to Philadelphia flights
George Bush Intcntl to O'Hare Intl flights
Hobby to Honolulu flights
George Bush Intcntl to Dulles Intl flights
Hobby to Boston flights
Hobby to Miami flights
George Bush Intcntl to Atlanta flights
George Bush Intcntl to San Francisco flights
George Bush Intcntl to Baltimore flights
George Bush Intcntl to Philadelphia flights
George Bush Intcntl to Nashville flights
George Bush Intcntl to Reagan-National flights
George Bush Intcntl to Honolulu flights
Hobby to Fort Lauderdale flights

Top 6 airlines flying from Hobby to Caribbean Islands

Discover the top 6 airlines that operate flights from Hobby to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$560FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$119Average$387FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$420FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$165Average$688FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$170Average$640FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$670FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.