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Caribbean

$93+ Cheap flights from Hobby (HOU) to Caribbean

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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Hobby to Caribbean

Keep the following information in mind while searching for Hobby to Caribbean flight deals. Data was last updated September 11, 2025.

Round-trip from

$185
(Delta)

One-way from

$93
(Delta)

Popular in

December

Cheapest in

October

Average price

$293
From Houston Hobby to Caribbean
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One-way flight from Houston Hobby to Caribbean
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Highest demand for flights based on searches. 12% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($14 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

Cheapest flights from Hobby to Caribbean
Explore the most affordable flight options available from Hobby to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/171:13 pmHOU - SJU
1 stop7h 47mDelta
Sat 9/277:30 amSJU - HOU
1 stop11h 10mDelta
Deal found 9/11$185
This Southwest deal was found by Cheapflights users on 9/10. 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 10/510:05 amHOU - SJU
1 stop9h 35mSouthwest
Thu 10/91:05 pmSJU - HOU
1 stop9h 30mSouthwest
Deal found 9/10$195
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sun 9/288:32 pmHOU - SJU
1 stop16h 43mAmerican Airlines
Fri 10/33:05 pmSJU - HOU
1 stop18h 26mAmerican Airlines
Deal found 9/11$215
This American Airlines deal was found by Cheapflights users on 9/10. 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
Sat 9/273:05 pmSJU - HOU
1 stop18h 24mAmerican Airlines
Deal found 9/10$220
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/206:00 amHOU - SJU
1 stop7h 15mAmerican Airlines
Sat 9/273:05 pmSJU - HOU
1 stop18h 24mAmerican Airlines
Deal found 9/9$245
This Southwest deal was found by Cheapflights users on 9/10. 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 10/56:30 amHOU - SJU
1 stop8h 20mSouthwest
Fri 10/101:05 pmSJU - HOU
1 stop9h 30mSouthwest
Deal found 9/10$255
This American Airlines deal was found by Cheapflights users on 9/11. 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 9/226:00 amHOU - SJU
1 stop7h 15mAmerican Airlines
Fri 9/263:05 pmSJU - HOU
1 stop18h 26mAmerican Airlines
Deal found 9/11$260
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/56:00 amHOU - SJU
1 stop7h 15mAmerican Airlines
Wed 10/83:34 pmSJU - HOU
1 stop17h 55mAmerican Airlines
Deal found 9/9$280
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/286:00 amHOU - SJU
1 stop7h 25mAmerican Airlines
Sat 11/13:34 pmSJU - HOU
1 stop7h 40mAmerican Airlines
Deal found 9/9$285
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/216:00 amHOU - SJU
2 stops11h 15mAmerican Airlines
Fri 9/263:05 pmSJU - HOU
1 stop18h 26mAmerican Airlines
Deal found 9/9$300
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 10/256:39 pmHOU - PUJ
1 stop20h 00mAmerican Airlines
Mon 11/34:05 pmPUJ - HOU
1 stop18h 32mAmerican Airlines
Deal found 9/11$382
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 10/188:45 amHOU - MBJ
Nonstop3h 10mSouthwest
Tue 10/2112:20 pmMBJ - HOU
1 stop10h 30mSouthwest
Deal found 9/9$432

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hobby to Caribbean 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 11, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to Caribbean that are best for you.

Fly from

Hobby

Fly to

Caribbean

Route

Depart

Return

Price

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 10/5

6:30 am-3:50 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Thu 10/9

5:50 am-7:55 pm

1 stop15h 05m

$195

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 10/26

3:00 pm-12:15 am

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Sun 11/2

5:40 am-12:35 pm

1 stop8h 55m

$295

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 10/21

2:22 pm-9:59 pm

1 stop6h 37m

San Juan Luis Munoz Marin Intl

Fri 10/24

7:15 am-5:48 pm

1 stop11h 33m

$305

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Wed 9/17

1:13 pm-10:00 pm

1 stop7h 47m

San Juan Luis Munoz Marin Intl

Wed 9/24

2:26 pm-10:37 pm

1 stop9h 11m

$318

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Wed 9/17

1:13 pm-10:00 pm

1 stop7h 47m

San Juan Luis Munoz Marin Intl

Fri 9/26

2:26 pm-10:37 pm

1 stop9h 11m

$318

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 9/21

6:00 am-4:31 pm

1 stop9h 31m

San Juan Luis Munoz Marin Intl

Sat 9/27

7:30 am-5:40 pm

1 stop11h 10m

$318

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 10/5

10:05 am-8:40 pm

1 stop9h 35m

San Juan Luis Munoz Marin Intl

Sat 10/11

5:45 am-7:20 pm

2 stops14h 35m

$350

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Wed 10/8

8:10 am-8:45 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Wed 10/22

2:45 pm-8:25 pm

1 stop6h 40m

$355

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 11/13

10:00 am-1:25 am

2 stops13h 25m

San Juan Luis Munoz Marin Intl

Wed 11/19

6:40 am-7:45 pm

2 stops15h 05m

$355

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Thu 11/13

8:20 pm-4:47 pm

1 stop18h 27m

Punta Cana

Tue 11/18

5:24 pm-8:37 am

2 stops17h 13m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results
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Best time to book a flight from Hobby to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean (average of $254). Flying from Houston Hobby Airport to Caribbean 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 CB?

Find hourly flight availability from Hobby to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

When flying from Houston Hobby Airport to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Houston Hobby Airport to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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. 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?

    A quick flight from Houston Hobby Airport to Caribbean can take about 6h 37m. Southwest provides one of the quickest options available for as low as $305. Houston Hobby Airport and Caribbean are separated by a distance of 1994 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $93 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Southwest and American Airlines, with prices starting from $158 and $177, respectively.

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

    Most travelers choose Houston Hobby - San Juan Luis Munoz Marin Intl, Houston Hobby - Montego Bay Sangster Intl or Houston Hobby - Punta Cana when deciding on the best route from Houston Hobby Airport to Caribbean.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Hobby to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean (average of $254). Flying from Houston Hobby Airport to Caribbean 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

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

Discover the top 6 airlines that operate flights from Hobby to Caribbean. 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$551FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$120Average$385FlexibilityNo cancel feeOn-time65%
FrontierCheapest$130Average$417FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$165Average$693FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$175Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$216Average$670FlexibilityNo cancel feeOn-time69%

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