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$109+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Hobby to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$297
(American Airlines)

One-way from

$109
(American Airlines)
From Houston Hobby to Caribbean
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One-way 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 January 21, 2025.

This American Airlines deal was found by Cheapflights users on 1/20. 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 4/88:16 pmHOU - SJU
1 stop7h 34mAmerican Airlines
Wed 4/93:20 pmSJU - HOU
1 stop8h 21mAmerican Airlines
Deal found 1/20$297
This Southwest deal was found by Cheapflights users on 1/20. 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 4/148:45 pmHOU - SJU
1 stop12h 35mSouthwest
Sat 4/264:00 pmSJU - HOU
1 stop7h 55mSouthwest
Deal found 1/20$306
This eDestinos deal was found by Cheapflights users on 1/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2012:00 pmHOU - SJU
1 stop23h 38mMultiple Airlines
Mon 3/249:35 pmSJU - HOU
3 stops37h 01mMultiple Airlines
Deal found 1/20$439
This Delta deal was found by Cheapflights users on 1/20. 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 2/126:00 amHOU - SJU
1 stop6h 36mDelta
Wed 2/194:15 pmSJU - HOU
1 stop8h 14mDelta
Deal found 1/20$486
This Southwest deal was found by Cheapflights users on 1/20. 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 3/46:20 amHOU - MBJ
1 stop5h 25mSouthwest
Sat 3/84:00 pmMBJ - HOU
Nonstop3h 35mSouthwest
Deal found 1/20$504
This American Airlines deal was found by Cheapflights users on 1/20. 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 3/57:00 amHOU - SDQ
2 stops12h 20mAmerican Airlines
Tue 3/115:00 amSDQ - HOU
2 stops11h 08mAmerican Airlines
Deal found 1/20$519
This Delta deal was found by Cheapflights users on 1/20. 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 2/246:00 amHOU - PUJ
1 stop6h 23mDelta
Tue 3/43:48 pmPUJ - HOU
1 stop8h 41mDelta
Deal found 1/20$525
This Southwest deal was found by Cheapflights users on 1/20. 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 3/115:55 amHOU - GCM
1 stop5h 50mSouthwest
Tue 3/1812:40 pmGCM - HOU
1 stop9h 20mSouthwest
Deal found 1/20$528
This American Airlines deal was found by Cheapflights users on 1/20. 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 4/56:16 pmHOU - PUJ
2 stops16h 38mAmerican Airlines
Tue 4/812:18 pmPUJ - HOU
1 stop11h 23mAmerican Airlines
Deal found 1/20$529
This Southwest deal was found by Cheapflights users on 1/20. 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 4/149:05 pmHOU - PLS
2 stops17h 05mSouthwest
Thu 4/174:05 pmPLS - HOU
2 stops18h 20mSouthwest
Deal found 1/20$536
This Delta deal was found by Cheapflights users on 1/20. 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 2/196:00 amHOU - MBJ
1 stop5h 47mDelta
Wed 2/268:00 amMBJ - HOU
1 stop7h 12mDelta
Deal found 1/20$541
This Delta deal was found by Cheapflights users on 1/20. 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 4/26:00 amHOU - NAS
1 stop6h 35mDelta
Tue 4/83:00 pmNAS - HOU
1 stop9h 02mDelta
Deal found 1/20$545

Find flights from Hobby to Caribbean within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 4/8

8:16 pm-4:50 am

1 stop7h 34m

San Juan Luis Munoz Marin Intl

Wed 4/9

3:20 pm-10:41 pm

1 stop8h 21m

$297

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Mon 4/14

8:45 pm-10:20 am

1 stop12h 35m

San Juan Luis Munoz Marin Intl

Sat 4/26

4:00 pm-10:55 pm

1 stop7h 55m

$306

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 2/25

10:25 am-9:06 pm

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Fri 2/28

6:15 am-2:12 pm

1 stop9h 57m

$432

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 3/20

12:00 pm-12:38 pm

1 stop23h 38m

San Juan Luis Munoz Marin Intl

Mon 3/24

9:35 pm-9:36 am

3 stops37h 01m

$439

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Tue 3/4

6:20 am-12:45 pm

1 stop5h 25m

Montego Bay Sangster Intl

Sat 3/8

4:00 pm-6:35 pm

Nonstop3h 35m

$504

HoustonSanto Domingo

HOU - SDQ

HOUSDQ

Houston Hobby

Wed 3/5

7:00 am-9:20 pm

2 stops12h 20m

Santo Domingo Las Americas

Tue 3/11

5:00 am-3:08 pm

2 stops11h 08m

$519

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Mon 2/24

6:00 am-2:23 pm

1 stop6h 23m

Punta Cana

Tue 3/4

3:48 pm-10:29 pm

1 stop8h 41m

$525

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Tue 3/11

5:55 am-11:45 am

1 stop5h 50m

George Town Owen Roberts Intl

Tue 3/18

12:40 pm-10:00 pm

1 stop9h 20m

$528

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Sat 4/5

6:16 pm-11:54 am

2 stops16h 38m

Punta Cana

Tue 4/8

12:18 pm-10:41 pm

1 stop11h 23m

$529

HoustonProvidenciales

HOU - PLS

HOUPLS

Houston Hobby

Mon 4/14

9:05 pm-3:10 pm

2 stops17h 05m

Providenciales

Thu 4/17

4:05 pm-9:25 am

2 stops18h 20m

$536

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 59 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.

Travel insights for flights from Hobby to Caribbean

Get recent, data-driven insights about flights from Hobby to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $378). 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 January 21, 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 January 21, 2025.
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

KLM
7.8
Good
1,341 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

LATAM Airlines
7.5
Good
1,858 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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?

    $109 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 Delta and Southwest, with prices starting from $138 and $154, 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.

  • 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 March is currently the most expensive (average of $378). 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$320FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$156Average$383FlexibilityNo cancel feeOn-time65%
DeltaCheapest$187Average$616FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$278Average$686FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$304Average$623FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$413Average$592FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$463Average$654FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$484Average$679FlexibilityNo cancel feeOn-time63%
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