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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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Oct 22 — Oct 291
Wed 10/22
Wed 10/29
1 adult, Economy
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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 September 22, 2025.

Round-trip from

$280
(American Airlines)

One-way from

$108
(Delta)

Popular in

December

Cheapest in

October

Average price

$344
From Houston Hobby to Caribbean Islands
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One-way flight from Houston Hobby to Caribbean Islands
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Highest demand for flights based on searches. 10% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 22, 2025.

This American Airlines deal was found by Cheapflights users on 9/20. 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 9/236:00 amHOU - SJU
2 stops11h 14mAmerican Airlines
Thu 9/253:05 pmSJU - HOU
1 stop18h 29mAmerican Airlines
Deal found 9/20$215
This American Airlines deal was found by Cheapflights users on 9/20. 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 9/246:00 amHOU - SJU
2 stops11h 14mAmerican Airlines
Fri 9/263:05 pmSJU - HOU
1 stop18h 26mAmerican Airlines
Deal found 9/20$235
This Southwest deal was found by Cheapflights users on 9/19. 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 10/218:10 amHOU - SJU
1 stop11h 35mSouthwest
Thu 10/231:05 pmSJU - HOU
1 stop9h 30mSouthwest
Deal found 9/19$295
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Thu 9/256:00 amHOU - SJU
2 stops11h 15mAmerican Airlines
Fri 9/263:05 pmSJU - HOU
1 stop18h 26mAmerican Airlines
Deal found 9/21$300
This Delta deal was found by Cheapflights users on 9/20. 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.
Tue 9/231:13 pmHOU - SJU
1 stop7h 47mDelta
Thu 9/252:26 pmSJU - HOU
1 stop9h 11mDelta
Deal found 9/20$325
This American Airlines deal was found by Cheapflights users on 9/20. 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 11/28:20 pmHOU - SJU
1 stop7h 50mAmerican Airlines
Sat 11/87:15 amSJU - HOU
1 stop12h 39mAmerican Airlines
Deal found 9/20$340
This Delta deal was found by Cheapflights users on 9/22. 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 9/251:13 pmHOU - SJU
1 stop7h 47mDelta
Thu 10/212:58 pmSJU - HOU
1 stop10h 39mDelta
Deal found 9/22$348
This American Airlines deal was found by Cheapflights users on 9/20. 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 10/68:11 pmHOU - SJU
1 stop17h 14mAmerican Airlines
Thu 10/93:10 pmSJU - HOU
1 stop7h 52mAmerican Airlines
Deal found 9/20$360
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/58:32 pmHOU - SJU
1 stop16h 48mAmerican Airlines
Wed 10/87:00 amSJU - HOU
2 stops10h 09mAmerican Airlines
Deal found 9/21$365
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Thu 9/256:00 amHOU - SJU
2 stops11h 15mAmerican Airlines
Sat 9/273:05 pmSJU - HOU
1 stop18h 24mAmerican Airlines
Deal found 9/21$370
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Sat 10/186:00 amHOU - SJU
2 stops8h 54mAmerican Airlines
Wed 10/227:00 amSJU - HOU
2 stops10h 09mAmerican Airlines
Deal found 9/20$385
This Southwest deal was found by Cheapflights users on 9/22. 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.
Sun 10/195:55 pmHOU - SJU
1 stop5h 55mSouthwest
Thu 10/231:05 pmSJU - HOU
1 stop9h 30mSouthwest
Deal found 9/22$395

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 September 22, 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

Tue 10/21

11:35 am-10:45 pm

2 stops10h 10m

San Juan Luis Munoz Marin Intl

Thu 10/23

5:50 am-4:40 pm

2 stops11h 50m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 10/19

5:55 pm-12:50 am

1 stop5h 55m

San Juan Luis Munoz Marin Intl

Thu 10/23

5:50 am-4:40 pm

2 stops11h 50m

$395

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 10/5

3:00 pm-12:15 am

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Thu 10/9

5:50 am-7:55 pm

1 stop15h 05m

$405

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Fri 1/16

1:05 pm-12:40 am

1 stop9h 35m

San Juan Luis Munoz Marin Intl

Sat 1/24

4:10 pm-7:30 pm

Nonstop5h 20m

$436

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Mon 12/8

5:44 am-2:56 pm

1 stop8h 12m

Montego Bay Sangster Intl

Tue 12/23

6:00 pm-8:32 am

1 stop15h 32m

$439

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sat 11/29

6:00 am-2:59 pm

1 stop7h 59m

Montego Bay Sangster Intl

Sat 12/6

1:51 pm-8:18 pm

1 stop7h 27m

$439

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Wed 12/10

11:15 am-11:20 pm

1 stop10h 05m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:40 am-1:35 pm

1 stop8h 55m

$440

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Wed 10/15

6:00 am-3:05 pm

2 stops9h 05m

Montego Bay Sangster Intl

Wed 10/22

1:00 pm-10:14 pm

1 stop9h 14m

$443

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sat 10/25

6:39 pm-9:13 am

2 stops14h 34m

Montego Bay Sangster Intl

Wed 10/29

1:00 pm-10:14 pm

1 stop9h 14m

$443

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Fri 12/5

11:15 am-11:20 pm

1 stop10h 05m

San Juan Luis Munoz Marin Intl

Mon 12/8

9:40 am-7:35 pm

1 stop11h 55m

$450

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/20

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, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean Islands (average of $254). Flying from Houston Hobby Airport to Caribbean Islands in June is currently the most expensive (average of $339). 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 September 22, 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 September 22, 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
4,244 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
8,922 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
8,031 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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 $482, Southwest can have you in Caribbean Islands from Houston Hobby Airport in 6h 41m. Houston Hobby Airport and Caribbean Islands are separated by a distance of 1785 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 $196 and $233 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, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean Islands (average of $254). Flying from Houston Hobby Airport to Caribbean Islands in June is currently the most expensive (average of $339). 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

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Alternative routes for Hobby to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$542FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$121Average$377FlexibilityNo cancel feeOn-time65%
FrontierCheapest$130Average$413FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$165Average$692FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$175Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$220Average$668FlexibilityNo cancel feeOn-time69%

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