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$115+ 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
ago. 3 — ago. 101
dom. 8/3
dom. 8/10
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 julio 29, 2025.

Round-trip from

$265
(American Airlines)

One-way from

$115
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$384

Good round-trip deal

$316 or less
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. 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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Price to beat on a round-trip flight from Houston Hobby to Caribbean.
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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 julio 29, 2025.

This American Airlines deal was found by Cheapflights users on 7/26. 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.
lun. 9/2210:15 amHOU - SJU
2 stops12h 22mAmerican Airlines
sáb. 9/273:05 pmSJU - HOU
1 stop18h 24mAmerican Airlines
Deal found 7/26$265
This Southwest deal was found by Cheapflights users on 7/27. 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.
lun. 8/1110:00 amHOU - SJU
2 stops9h 45mSouthwest
jue. 8/148:15 amSJU - HOU
2 stops13h 00mSouthwest
Deal found 7/27$330
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/248:25 pmHOU - PUJ
2 stops15h 25mAmerican Airlines
mar. 8/264:15 pmPUJ - HOU
2 stops18h 29mAmerican Airlines
Deal found 7/28$374
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/259:57 amHOU - SJU
1 stop11h 10mDelta
sáb. 9/67:30 amSJU - HOU
1 stop11h 09mDelta
Deal found 7/28$395
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.
lun. 9/18:25 pmHOU - AUA
2 stops18h 25mAmerican Airlines
jue. 9/44:50 pmAUA - HOU
2 stops16h 44mAmerican Airlines
Deal found 7/29$410
This Southwest deal was found by Cheapflights users on 7/27. 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.
mar. 12/96:00 amHOU - MBJ
1 stop7h 25mSouthwest
vie. 12/121:00 pmMBJ - HOU
2 stops9h 35mSouthwest
Deal found 7/27$419
This American Airlines deal was found by Cheapflights users on 7/27. 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.
sáb. 10/256:39 pmHOU - MBJ
2 stops14h 34mAmerican Airlines
mié. 10/291:00 pmMBJ - HOU
1 stop9h 14mAmerican Airlines
Deal found 7/27$423
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.
mié. 10/154:41 pmHOU - PLS
2 stops18h 49mAmerican Airlines
mar. 10/213:20 pmPLS - HOU
2 stops18h 07mAmerican Airlines
Deal found 7/29$438
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/2910:05 amHOU - MBJ
1 stop5h 28mDelta
mié. 12/33:32 pmMBJ - HOU
1 stop7h 08mDelta
Deal found 7/29$444
This Southwest deal was found by Cheapflights users on 7/28. 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.
lun. 8/255:05 amHOU - PUJ
1 stop7h 50mSouthwest
jue. 8/282:50 pmPUJ - HOU
1 stop9h 00mSouthwest
Deal found 7/28$445
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/96:00 amHOU - PUJ
1 stop7h 34mDelta
vie. 9/123:59 pmPUJ - HOU
1 stop7h 38mDelta
Deal found 7/29$455
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/76:00 amHOU - SDQ
1 stop6h 41mDelta
mié. 10/222:56 pmSDQ - HOU
1 stop9h 04mDelta
Deal found 7/28$515

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 julio 29, 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

lun. 9/22

10:15 am-11:37 pm

2 stops12h 22m

San Juan Luis Munoz Marin Intl

sáb. 9/27

3:05 pm-8:29 am

1 stop18h 24m

$265

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

lun. 8/11

10:00 am-8:45 pm

2 stops9h 45m

San Juan Luis Munoz Marin Intl

jue. 8/14

8:15 am-8:15 pm

2 stops13h 00m

$330

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

dom. 8/24

8:25 pm-12:50 pm

2 stops15h 25m

Punta Cana

mar. 8/26

4:15 pm-9:44 am

2 stops18h 29m

$374

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

lun. 8/25

1:05 pm-10:07 pm

1 stop8h 02m

San Juan Luis Munoz Marin Intl

vie. 9/19

7:30 am-5:40 pm

1 stop11h 10m

$395

HoustonOranjestad

HOU - AUA

HOUAUA

Houston Hobby

lun. 9/1

8:25 pm-3:50 pm

2 stops18h 25m

Oranjestad Reina Beatrix

jue. 9/4

4:50 pm-8:34 am

2 stops16h 44m

$410

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

lun. 9/1

6:00 am-3:36 pm

1 stop9h 36m

Montego Bay Sangster Intl

mié. 9/10

2:30 pm-10:31 pm

1 stop8h 01m

$419

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

sáb. 10/25

6:39 pm-9:13 am

2 stops14h 34m

Montego Bay Sangster Intl

mié. 10/29

1:00 pm-10:14 pm

1 stop9h 14m

$423

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

lun. 9/29

7:55 am-2:00 pm

1 stop6h 05m

Montego Bay Sangster Intl

sáb. 10/4

3:00 pm-6:20 pm

Nonstop3h 20m

$434

HoustonProvidenciales

HOU - PLS

HOUPLS

Houston Hobby

mié. 10/15

4:41 pm-12:30 pm

2 stops18h 49m

Providenciales

mar. 10/21

3:20 pm-8:27 am

2 stops18h 07m

$438

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

lun. 8/25

5:05 am-1:55 pm

1 stop7h 50m

Punta Cana

jue. 8/28

2:50 pm-10:50 pm

1 stop9h 00m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 54 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 julio 29, 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 julio 29, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Avelo 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
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

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
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

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
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

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
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

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. 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 one-way?

    $115 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Avelo Airlines and Southwest, with prices starting from $168 and $176, 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 - Punta Cana or Houston Hobby - Oranjestad Reina Beatrix when deciding on the best route from Houston Hobby Airport to Caribbean.

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

    Looking at all options, your cheapest flight can be booked for $261. While the most popular route (Houston Hobby - San Juan Luis Munoz Marin Intl) can be booked for $157 on average our data indicates $466 when flying 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 7 airlines flying from Hobby to Caribbean

Discover the top 7 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 julio 29, 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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