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$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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
May 4 — May 111
Sun 5/4
Sun 5/11
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 29, 2025.

Round-trip from

$161
(Southwest)

One-way from

$93
(Southwest)

Popular in

December

Cheapest in

September

Average price

$309

Good round-trip deal

$546 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 ($52 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 29, 2025.

This Southwest deal was found by Cheapflights users on 4/28. 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.
Sat 5/31:05 pmHOU - SJU
1 stop8h 20mSouthwest
Sat 5/103:40 pmSJU - HOU
Nonstop5h 10mSouthwest
Deal found 4/28$161
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Mon 5/58:16 pmHOU - SJU
1 stop7h 56mAmerican Airlines
Fri 5/96:30 amSJU - HOU
1 stop14h 14mAmerican Airlines
Deal found 4/28$210
This Delta deal was found by Cheapflights users on 4/28. 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.
Sat 5/34:00 pmHOU - SJU
1 stop6h 15mDelta
Tue 5/65:11 pmSJU - HOU
1 stop6h 57mDelta
Deal found 4/28$215
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Mon 5/195:00 amHOU - MBJ
1 stop9h 35mAmerican Airlines
Fri 5/2310:53 amMBJ - HOU
1 stop8h 51mAmerican Airlines
Deal found 4/28$449
This Southwest deal was found by Cheapflights users on 4/28. 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.
Sun 6/85:10 amHOU - MBJ
1 stop9h 45mSouthwest
Thu 6/123:55 pmMBJ - HOU
Nonstop3h 15mSouthwest
Deal found 4/28$464
This Delta deal was found by Cheapflights users on 4/28. 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.
Tue 5/206:00 amHOU - MBJ
1 stop9h 30mDelta
Sat 5/242:23 pmMBJ - HOU
1 stop6h 54mDelta
Deal found 4/28$474
This Delta deal was found by Cheapflights users on 4/29. 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.
Mon 8/186:00 amHOU - PUJ
1 stop7h 32mDelta
Fri 8/221:10 pmPUJ - HOU
1 stop9h 25mDelta
Deal found 4/29$477
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Sat 9/206:41 pmHOU - PUJ
2 stops16h 51mAmerican Airlines
Tue 9/235:35 pmPUJ - HOU
2 stops17h 13mAmerican Airlines
Deal found 4/28$479
This Southwest deal was found by Cheapflights users on 4/29. 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.
Tue 7/87:35 amHOU - PUJ
1 stop5h 55mSouthwest
Sat 7/123:40 pmPUJ - HOU
1 stop9h 15mSouthwest
Deal found 4/29$521
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/288:23 pmHOU - NAS
1 stop15h 27mAmerican Airlines
Fri 7/46:25 pmNAS - HOU
1 stop16h 20mAmerican Airlines
Deal found 4/29$525
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 10/146:00 amHOU - NAS
1 stop6h 11mDelta
Wed 10/222:36 pmNAS - HOU
1 stop8h 04mDelta
Deal found 4/29$526
This Delta deal was found by Cheapflights users on 4/28. 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.
Sat 9/136:00 amHOU - SDQ
1 stop6h 47mDelta
Fri 9/193:12 pmSDQ - HOU
1 stop7h 28mDelta
Deal found 4/28$535

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 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

Sat 5/3

1:05 pm-10:25 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Sat 5/10

3:40 pm-7:50 pm

Nonstop5h 10m

$161

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Mon 5/5

8:16 pm-5:12 am

1 stop7h 56m

San Juan Luis Munoz Marin Intl

Fri 5/9

6:30 am-7:44 pm

1 stop14h 14m

$210

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sat 5/3

4:00 pm-11:15 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Tue 5/6

5:11 pm-11:08 pm

1 stop6h 57m

$215

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Mon 5/19

5:00 am-2:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Fri 5/23

10:53 am-7:44 pm

1 stop8h 51m

$449

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sun 6/8

5:10 am-2:55 pm

1 stop9h 45m

Montego Bay Sangster Intl

Thu 6/12

3:55 pm-7:10 pm

Nonstop3h 15m

$464

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Tue 5/20

6:00 am-3:30 pm

1 stop9h 30m

Montego Bay Sangster Intl

Sat 5/24

2:23 pm-9:17 pm

1 stop6h 54m

$474

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Tue 7/8

7:35 am-2:30 pm

1 stop5h 55m

Punta Cana

Sat 7/12

3:40 pm-11:55 pm

1 stop9h 15m

$521

HoustonNassau

HOU - NAS

HOUNAS

Houston Hobby

Sat 6/28

8:23 pm-12:50 pm

1 stop15h 27m

Nassau Intl

Fri 7/4

6:25 pm-9:45 am

1 stop16h 20m

$525

HoustonNassau

HOU - NAS

HOUNAS

Houston Hobby

Tue 10/14

6:00 am-1:11 pm

1 stop6h 11m

Nassau Intl

Fri 10/24

2:36 pm-9:40 pm

1 stop8h 04m

$526

HoustonSanto Domingo

HOU - SDQ

HOUSDQ

Houston Hobby

Sat 9/13

6:00 am-1:47 pm

1 stop6h 47m

Santo Domingo Las Americas

Fri 9/19

3:12 pm-9:40 pm

1 stop7h 28m

$535

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 58 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 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.

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 29, 2025.
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
LATAM Airlines
7.5
Good
1,767 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,823 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $93 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 $98 and $113, 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 $110 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$128Average$405FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$354FlexibilityNo cancel feeOn-time62%
DeltaCheapest$197Average$575FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$238Average$671FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$244Average$661FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$297Average$689FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$413Average$592FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$463Average$654FlexibilityNo cancel feeOn-time70%

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