Caribbean Islands

$78+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Jun 17 — Jun 241
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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 June 12, 2025.

Round-trip from

$185
(American Airlines)

One-way from

$78
(Southwest)

Popular in

December

Cheapest in

September

Average price

$328
From Houston Hobby to Caribbean Islands
One-way flight from Houston Hobby to Caribbean Islands
Highest demand for flights based on searches. 15% potential increase in price ($57 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Average for round-trip flights in June 2025

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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 6/148:56 amHOU - SJU
1 stop13h 29mAmerican Airlines
Thu 6/1912:59 amSJU - HOU
1 stop8h 27mAmerican Airlines
Deal found 6/11$185
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/231:00 pmHOU - SJU
1 stop8h 08mDelta
Wed 10/12:28 pmSJU - HOU
1 stop8h 12mDelta
Deal found 6/9$215
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 9/3011:25 amHOU - SJU
1 stop7h 20mSouthwest
Mon 10/610:05 amSJU - HOU
2 stops12h 35mSouthwest
Deal found 6/10$260
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/66:44 pmHOU - MBJ
2 stops17h 21mAmerican Airlines
Wed 9/103:36 pmMBJ - HOU
2 stops16h 53mAmerican Airlines
Deal found 6/11$345
This Delta deal was found by Cheapflights users on 6/11. 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.
Sun 12/76:00 amHOU - MBJ
1 stop9h 33mDelta
Fri 12/123:32 pmMBJ - HOU
1 stop7h 08mDelta
Deal found 6/11$380
This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 8/226:00 amHOU - PUJ
1 stop7h 34mDelta
Tue 8/262:40 pmPUJ - HOU
1 stop8h 51mDelta
Deal found 6/11$400
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 9/126:44 pmHOU - PUJ
2 stops16h 51mAmerican Airlines
Tue 9/164:25 pmPUJ - HOU
2 stops18h 16mAmerican Airlines
Deal found 6/11$401
This Mytrip deal was found by Cheapflights users on 6/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/18:03 pmHOU - STT
3 stops36h 45mMultiple Airlines
Thu 8/710:43 amSTT - HOU
2 stops33h 30mMultiple Airlines
Deal found 6/9$405
This Southwest deal was found by Cheapflights users on 6/10. 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.
Sat 11/18:45 amHOU - MBJ
Nonstop3h 10mSouthwest
Wed 11/53:45 pmMBJ - HOU
1 stop6h 10mSouthwest
Deal found 6/10$410
This Southwest deal was found by Cheapflights users on 6/12. 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.
Wed 8/206:30 amHOU - PUJ
1 stop6h 25mSouthwest
Mon 8/252:50 pmPUJ - HOU
1 stop9h 00mSouthwest
Deal found 6/12$455
This Southwest deal was found by Cheapflights users on 6/11. 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 11/46:40 amHOU - GCM
1 stop4h 55mSouthwest
Sun 11/91:30 pmGCM - HOU
1 stop7h 00mSouthwest
Deal found 6/11$485
This Delta deal was found by Cheapflights users on 6/11. 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.
Tue 10/146:00 amHOU - SDQ
1 stop6h 53mDelta
Thu 10/303:15 pmSDQ - HOU
1 stop7h 25mDelta
Deal found 6/11$495

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 June 12, 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

Sun 6/15

8:23 pm-5:06 am

1 stop7h 43m

San Juan Luis Munoz Marin Intl

Thu 6/19

12:59 am-8:26 am

1 stop8h 27m

$185

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 8/31

1:05 pm-10:07 pm

1 stop8h 02m

San Juan Luis Munoz Marin Intl

Sat 9/6

7:30 am-5:39 pm

1 stop11h 09m

$215

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Wed 8/13

11:25 am-7:45 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Fri 8/22

8:15 am-8:15 pm

2 stops13h 00m

$260

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sat 9/6

6:44 pm-12:05 pm

2 stops17h 21m

Montego Bay Sangster Intl

Wed 9/10

3:36 pm-8:29 am

2 stops16h 53m

$345

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sun 12/7

6:00 am-4:33 pm

1 stop9h 33m

Montego Bay Sangster Intl

Fri 12/12

3:32 pm-9:40 pm

1 stop7h 08m

$380

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Fri 8/22

6:00 am-2:34 pm

1 stop7h 34m

Punta Cana

Tue 8/26

2:40 pm-10:31 pm

1 stop8h 51m

$400

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Fri 9/12

6:44 pm-12:35 pm

2 stops16h 51m

Punta Cana

Tue 9/16

4:25 pm-9:41 am

2 stops18h 16m

$401

HoustonSaint Thomas Island

HOU - STT

HOUSTT

Houston Hobby

Fri 8/1

8:03 pm-9:48 am

3 stops36h 45m

Saint Thomas Island Cyril E King

Thu 8/7

10:43 am-7:13 pm

2 stops33h 30m

$405

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sat 11/1

8:45 am-11:55 am

Nonstop3h 10m

Montego Bay Sangster Intl

Wed 11/5

3:45 pm-8:55 pm

1 stop6h 10m

$410

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Wed 8/20

6:30 am-1:55 pm

1 stop6h 25m

Punta Cana

Mon 8/25

2:50 pm-10:50 pm

1 stop9h 00m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 June 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and LATAM Airlines from Houston to Caribbean Islands by reading reviews from past customers. 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.

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
8.0
Very good

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $78. Users have also found prices from $83 and $108 on American Airlines and Delta, respectively.

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

  • What are the cheapest flights from Houston Hobby Airport to Caribbean Islands?

    The cheapest flight price from Houston Hobby Airport to Caribbean Islands is $506. On average you can expect to pay $590. The most popular route, (Houston Hobby - San Juan Luis Munoz Marin Intl), can usually be booked for $155.

  • 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.

Top 7 airlines flying from Hobby to Caribbean Islands

Discover the top 7 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$123Average$405FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$406FlexibilityNo cancel feeOn-time62%
DeltaCheapest$138Average$594FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$175Average$656FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$230Average$670FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$297Average$700FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$413Average$592FlexibilityNo cancel feeOn-time62%

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