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$73+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Round-trip from

$210
(American Airlines)

One-way from

$73
(Southwest)

Popular in

December

Cheapest in

September

Average price

$324

Good round-trip deal

$606 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. 12% potential increase in price ($49 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 April 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 April 17, 2025.

This American Airlines deal was found by Cheapflights users on 4/17. 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 4/266:31 pmHOU - SJU
1 stop9h 29mAmerican Airlines
Tue 4/296:05 amSJU - HOU
1 stop14h 36mAmerican Airlines
Deal found 4/17$210
This Southwest deal was found by Cheapflights users on 4/16. 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 5/101:05 pmHOU - SJU
1 stop8h 20mSouthwest
Wed 5/147:00 amSJU - HOU
1 stop7h 15mSouthwest
Deal found 4/16$250
This Delta deal was found by Cheapflights users on 4/17. 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 4/296:00 amHOU - SJU
1 stop7h 19mDelta
Sat 5/37:15 amSJU - HOU
1 stop11h 32mDelta
Deal found 4/17$295
This Delta deal was found by Cheapflights users on 4/17. 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 9/76:00 amHOU - PUJ
1 stop6h 17mDelta
Thu 9/112:42 pmPUJ - HOU
1 stop7h 58mDelta
Deal found 4/17$391
This Delta deal was found by Cheapflights users on 4/16. 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.
Sat 5/176:00 amHOU - MBJ
1 stop9h 30mDelta
Wed 5/211:02 pmMBJ - HOU
1 stop8h 15mDelta
Deal found 4/16$421
This American Airlines deal was found by Cheapflights users on 4/17. 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 10/258:10 pmHOU - MBJ
2 stops15h 00mAmerican Airlines
Wed 10/293:18 pmMBJ - HOU
1 stop6h 56mAmerican Airlines
Deal found 4/17$453
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/188:16 pmHOU - PUJ
2 stops16h 19mAmerican Airlines
Thu 5/2211:46 amPUJ - HOU
1 stop13h 12mAmerican Airlines
Deal found 4/17$489
This Southwest deal was found by Cheapflights users on 4/17. 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 6/85:10 amHOU - MBJ
1 stop9h 45mSouthwest
Fri 6/132:55 pmMBJ - HOU
1 stop8h 30mSouthwest
Deal found 4/17$513
This Delta deal was found by Cheapflights users on 4/16. 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 5/146:00 amHOU - SDQ
1 stop6h 16mDelta
Wed 5/212:41 pmSDQ - HOU
1 stop7h 36mDelta
Deal found 4/16$515
This American Airlines deal was found by Cheapflights users on 4/17. 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 8/145:00 amHOU - SDQ
2 stops8h 40mAmerican Airlines
Wed 8/2011:30 amSDQ - HOU
2 stops9h 33mAmerican Airlines
Deal found 4/17$519
This American Airlines deal was found by Cheapflights users on 4/17. 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 7/110:13 amHOU - NAS
1 stop6h 12mAmerican Airlines
Tue 7/86:25 pmNAS - HOU
1 stop6h 24mAmerican Airlines
Deal found 4/17$525
This Southwest deal was found by Cheapflights users on 4/17. 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.
Mon 7/2110:40 pmHOU - NAS
2 stops13h 35mSouthwest
Thu 7/242:10 pmNAS - HOU
1 stop6h 35mSouthwest
Deal found 4/17$529

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 April 17, 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

Sat 4/26

6:31 pm-5:00 am

1 stop9h 29m

San Juan Luis Munoz Marin Intl

Tue 4/29

6:05 am-7:41 pm

1 stop14h 36m

$210

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sat 5/10

1:05 pm-10:25 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Wed 5/14

7:00 am-1:15 pm

1 stop7h 15m

$250

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 4/29

6:00 am-2:19 pm

1 stop7h 19m

San Juan Luis Munoz Marin Intl

Sat 5/3

7:15 am-5:47 pm

1 stop11h 32m

$295

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Sun 9/7

6:00 am-1:17 pm

1 stop6h 17m

Punta Cana

Thu 9/11

2:42 pm-9:40 pm

1 stop7h 58m

$391

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sat 5/17

6:00 am-3:30 pm

1 stop9h 30m

Montego Bay Sangster Intl

Wed 5/21

1:02 pm-9:17 pm

1 stop8h 15m

$421

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sun 5/18

5:00 am-1:35 pm

2 stops8h 35m

Montego Bay Sangster Intl

Wed 5/21

12:54 pm-11:58 pm

2 stops11h 04m

$458

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Sun 5/18

8:16 pm-1:35 pm

2 stops16h 19m

Punta Cana

Thu 5/22

11:46 am-11:58 pm

1 stop13h 12m

$489

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sun 6/8

5:10 am-2:55 pm

1 stop9h 45m

Montego Bay Sangster Intl

Fri 6/13

2:55 pm-11:25 pm

1 stop8h 30m

$513

HoustonSanto Domingo

HOU - SDQ

HOUSDQ

Houston Hobby

Wed 5/14

6:00 am-1:16 pm

1 stop6h 16m

Santo Domingo Las Americas

Wed 5/21

2:41 pm-9:17 pm

1 stop7h 36m

$515

HoustonSanto Domingo

HOU - SDQ

HOUSDQ

Houston Hobby

Thu 8/14

5:00 am-2:40 pm

2 stops8h 40m

Santo Domingo Las Americas

Wed 8/20

11:30 am-8:03 pm

2 stops9h 33m

$519

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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 December is currently the most expensive (average of $336). 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 April 17, 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.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

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 April 17, 2025.
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,916 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
LATAM Airlines
7.5
Good
1,761 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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?

    $73 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $99 and $147, 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 - Montego Bay Sangster Intl 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 $250. While the most popular route (Houston Hobby - San Juan Luis Munoz Marin Intl) can be booked for $135 on average our data indicates $636 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 December is currently the most expensive (average of $336). 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 8 airlines flying from Hobby to Caribbean

Discover the top 8 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$127Average$398FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$347FlexibilityNo cancel feeOn-time62%
DeltaCheapest$144Average$565FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$242Average$670FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$250Average$660FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$297Average$686FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$413Average$592FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$463Average$654FlexibilityNo cancel feeOn-time70%

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