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Caribbean Islands

$158+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
1 adult, Economy
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Cheap 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 December 31, 2025.

This American Airlines deal was found by Cheapflights users on 12/30. 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 12/304:21 pmHOU - SJU
1 stop11h 13mAmerican Airlines
Tue 2/33:54 pmSJU - HOU
1 stop8h 52mAmerican Airlines
Deal found 12/30$555
This Southwest deal was found by Cheapflights users on 12/28. 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 12/309:50 amHOU - SJU
2 stops9h 00mSouthwest
Sat 1/109:10 amSJU - HOU
2 stops9h 45mSouthwest
Deal found 12/28$695
This American Airlines deal was found by Cheapflights users on 12/29. 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 12/308:16 pmHOU - SJU
1 stop7h 18mAmerican Airlines
Thu 1/17:00 amSJU - HOU
1 stop10h 47mAmerican Airlines
Deal found 12/29$705
This Southwest deal was found by Cheapflights users on 12/29. 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 12/309:50 amHOU - SJU
2 stops9h 00mSouthwest
Thu 1/16:40 amSJU - HOU
2 stops15h 05mSouthwest
Deal found 12/29$715
This American Airlines deal was found by Cheapflights users on 12/29. 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 12/3012:09 pmHOU - SJU
1 stop9h 13mAmerican Airlines
Tue 12/301:30 amSJU - HOU
1 stop10h 13mAmerican Airlines
Deal found 12/29$720
This Southwest deal was found by Cheapflights users on 12/29. 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 12/3010:30 amHOU - SJU
2 stops12h 55mSouthwest
Wed 12/315:45 amSJU - HOU
2 stops8h 50mSouthwest
Deal found 12/29$730
This Southwest deal was found by Cheapflights users on 12/28. 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 12/298:40 pmHOU - SJU
1 stop12h 05mSouthwest
Thu 1/15:45 amSJU - HOU
2 stops10h 00mSouthwest
Deal found 12/28$735
This Southwest deal was found by Cheapflights users on 12/29. 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 12/2910:40 pmHOU - SJU
2 stops16h 40mSouthwest
Sat 1/109:10 amSJU - HOU
2 stops9h 45mSouthwest
Deal found 12/29$745
This American Airlines deal was found by Cheapflights users on 12/29. 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 12/298:16 pmHOU - SJU
1 stop7h 18mAmerican Airlines
Sat 1/107:07 amSJU - HOU
1 stop12h 59mAmerican Airlines
Deal found 12/29$755
This Southwest deal was found by Cheapflights users on 12/30. 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 12/302:50 pmHOU - SJU
2 stops8h 50mSouthwest
Mon 1/56:10 amSJU - HOU
1 stop15h 40mSouthwest
Deal found 12/30$785
This Southwest deal was found by Cheapflights users on 12/30. 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.
Wed 12/316:40 amHOU - NAS
1 stop4h 35mSouthwest
Wed 1/71:55 pmNAS - HOU
1 stop7h 15mSouthwest
Deal found 12/30$801
This Southwest deal was found by Cheapflights users on 12/29. 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 12/298:40 pmHOU - SJU
1 stop12h 05mSouthwest
Fri 1/26:05 amSJU - HOU
2 stops9h 40mSouthwest
Deal found 12/29$865

Find 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 December 31, 2025.

Round-trip from

$383
(Delta)

One-way from

$158
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$490
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. 12% potential increase in price ($52 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 December 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 December 31, 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

HoustonChristiansted

HOU - STX

HOUSTX

Houston Hobby

Wed 1/28

5:45 am-2:33 pm

1 stop6h 48m

Christiansted Henry Rohlsen

Wed 2/4

3:33 pm-10:33 pm

1 stop9h 00m

$383

HoustonChristiansted

HOU - STX

HOUSTX

Houston Hobby

Wed 1/28

10:35 am-9:31 pm

2 stops8h 56m

Christiansted Henry Rohlsen

Wed 2/4

8:30 am-6:06 pm

2 stops11h 36m

$387

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Mon 2/2

8:00 am-8:55 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

Thu 2/5

5:35 am-1:20 pm

2 stops9h 45m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 1/27

11:09 am-8:58 pm

1 stop7h 49m

San Juan Luis Munoz Marin Intl

Thu 2/5

2:15 pm-10:33 pm

1 stop10h 18m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 2/5

10:00 am-9:50 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Tue 2/10

9:05 am-7:45 pm

1 stop12h 40m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Wed 1/28

5:45 am-5:17 pm

1 stop9h 32m

San Juan Luis Munoz Marin Intl

Thu 2/5

2:15 pm-10:33 pm

1 stop10h 18m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 1/20

1:35 pm-12:35 am

2 stops9h 00m

San Juan Luis Munoz Marin Intl

Tue 1/27

9:05 am-7:45 pm

1 stop12h 40m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Fri 1/23

11:15 am-11:10 pm

2 stops9h 55m

San Juan Luis Munoz Marin Intl

Wed 1/28

9:05 am-7:45 pm

1 stop12h 40m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 1/27

11:09 am-8:58 pm

1 stop7h 49m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:15 pm-10:33 pm

1 stop10h 18m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 3/17

11:05 am-11:00 pm

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Wed 3/25

5:55 am-1:40 pm

2 stops8h 45m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 60 results
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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 $94). Flying from Houston Hobby Airport to Caribbean Islands in December is currently the most expensive (average of $154). 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 December 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Houston Hobby Airport to Caribbean Islands as you normally would.

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 December 31, 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
4,253 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,013 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,128 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,070 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,253 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 $383, Delta can have you in Caribbean Islands from Houston Hobby Airport in 6h 48m. Houston Hobby Airport and Caribbean Islands are separated by a distance of 2088 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 Spirit Airlines. According to our data, you can fly for as low as $59. Users have also found prices from $72 and $72 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 $94). Flying from Houston Hobby Airport to Caribbean Islands in December is currently the most expensive (average of $154). 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.

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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 December 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$550FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$119Average$376FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$417FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$165Average$697FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$170Average$635FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$223Average$664FlexibilityNo cancel feeOn-time69%

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