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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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$225
(Delta)

One-way from

$108
(Delta)

Popular in

December

Cheapest in

September

Average price

$384
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. 13% potential increase in price ($53 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 July 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 July 31, 2025.

This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2310:44 amHOU - SJU
1 stop10h 16mDelta
Thu 10/212:58 pmSJU - HOU
1 stop10h 39mDelta
Deal found 7/30$225
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/36:30 pmHOU - SJU
1 stop9h 36mAmerican Airlines
Tue 8/56:15 amSJU - HOU
1 stop14h 38mAmerican Airlines
Deal found 7/31$240
This Southwest deal was found by Cheapflights users on 7/31. 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 9/183:20 pmHOU - SJU
1 stop7h 30mSouthwest
Sun 9/2110:30 pmSJU - HOU
1 stop10h 25mSouthwest
Deal found 7/31$263
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/18:25 pmHOU - AUA
2 stops18h 25mAmerican Airlines
Thu 9/44:50 pmAUA - HOU
2 stops16h 44mAmerican Airlines
Deal found 7/29$410
This Delta deal was found by Cheapflights users on 7/31. 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 9/286:00 amHOU - MBJ
1 stop7h 09mDelta
Thu 10/21:25 pmMBJ - HOU
1 stop9h 12mDelta
Deal found 7/31$419
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sun 9/2810:05 pmHOU - MBJ
2 stops15h 55mSouthwest
Thu 10/22:55 pmMBJ - HOU
2 stops8h 20mSouthwest
Deal found 7/29$423
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 10/256:39 pmHOU - MBJ
1 stop19h 36mAmerican Airlines
Wed 10/291:00 pmMBJ - HOU
1 stop9h 14mAmerican Airlines
Deal found 7/30$425
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:00 amHOU - PUJ
1 stop6h 23mDelta
Tue 11/183:50 pmPUJ - HOU
1 stop7h 50mDelta
Deal found 7/30$435
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 11/86:37 pmHOU - PUJ
2 stops15h 03mAmerican Airlines
Wed 11/125:33 pmPUJ - HOU
2 stops17h 02mAmerican Airlines
Deal found 7/30$439
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 8/166:30 pmHOU - UVF
2 stops19h 05mAmerican Airlines
Wed 8/203:35 pmUVF - HOU
2 stops17h 46mAmerican Airlines
Deal found 7/29$448
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/276:00 amHOU - SDQ
2 stops11h 20mAmerican Airlines
Wed 9/37:00 amSDQ - HOU
2 stops12h 10mAmerican Airlines
Deal found 7/31$449
This Southwest deal was found by Cheapflights users on 7/30. 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 11/46:40 amHOU - PLS
1 stop6h 05mSouthwest
Sun 11/92:40 pmPLS - HOU
1 stop8h 50mSouthwest
Deal found 7/30$485

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 July 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

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 9/23

10:44 am-10:00 pm

1 stop10h 16m

San Juan Luis Munoz Marin Intl

Thu 10/2

12:58 pm-10:37 pm

1 stop10h 39m

$225

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 8/3

6:30 pm-5:06 am

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Tue 8/5

6:15 am-7:53 pm

1 stop14h 38m

$240

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 9/18

3:20 pm-11:50 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Sun 9/21

10:30 pm-7:55 am

1 stop10h 25m

$263

HoustonOranjestad

HOU - AUA

HOUAUA

Houston Hobby

Mon 9/1

8:25 pm-3:50 pm

2 stops18h 25m

Oranjestad Reina Beatrix

Thu 9/4

4:50 pm-8:34 am

2 stops16h 44m

$410

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sun 9/28

6:00 am-1:09 pm

1 stop7h 09m

Montego Bay Sangster Intl

Thu 10/2

1:25 pm-10:37 pm

1 stop9h 12m

$419

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sun 9/28

10:05 pm-2:00 pm

2 stops15h 55m

Montego Bay Sangster Intl

Thu 10/2

2:55 pm-11:15 pm

2 stops8h 20m

$423

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sat 10/25

4:41 pm-2:15 pm

1 stop21h 34m

Montego Bay Sangster Intl

Wed 10/29

1:00 pm-10:14 pm

1 stop9h 14m

$425

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Sun 9/28

6:00 am-2:32 pm

1 stop7h 32m

Punta Cana

Thu 10/2

2:45 pm-10:37 pm

1 stop8h 52m

$435

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Sun 9/28

10:05 pm-2:05 pm

2 stops15h 00m

Punta Cana

Thu 10/2

3:30 pm-11:45 pm

1 stop9h 15m

$439

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Thu 10/16

8:11 pm-3:39 pm

1 stop18h 28m

Punta Cana

Tue 10/21

4:30 pm-8:27 am

2 stops16h 57m

$446

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 58 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 July 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 July 31, 2025.
Read through reviews of airlines operating flights from Houston Hobby Airport to Caribbean Islands, such as Southwest, Delta, and Avelo 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
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
WestJet
7.2
Good
2,978 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Delta. According to our data, you can fly for as low as $108. Users have also found prices from $118 and $168 on American Airlines and Avelo Airlines, 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 - Oranjestad Reina Beatrix.

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

    The cheapest flight price from Houston Hobby Airport to Caribbean Islands is $261. On average you can expect to pay $466. The most popular route, (Houston Hobby - San Juan Luis Munoz Marin Intl), can usually be booked for $145.

  • 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.

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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 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$121Average$395FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$395FlexibilityNo cancel feeOn-time62%
DeltaCheapest$137Average$562FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$165Average$691FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$175Average$639FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$670FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$413Average$592FlexibilityNo cancel feeOn-time62%

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