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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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$262
(American Airlines)

One-way from

$109
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$306

Good round-trip deal

$647 or less

Good one-way deal

$275 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. 7% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Houston Hobby to Caribbean.
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Price to beat on a 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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/19. 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 2/246:31 pmHOU - SJU
1 stop8h 33mAmerican Airlines
Thu 2/274:01 pmSJU - HOU
1 stop9h 49mAmerican Airlines
Deal found 2/19$237
This Delta deal was found by Cheapflights users on 2/19. 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 2/262:57 pmHOU - SJU
1 stop6h 49mDelta
Wed 3/54:15 pmSJU - HOU
1 stop8h 14mDelta
Deal found 2/19$255
This Southwest deal was found by Cheapflights users on 2/20. 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 3/253:05 pmHOU - SJU
1 stop6h 45mSouthwest
Sat 3/296:15 pmSJU - HOU
Nonstop5h 05mSouthwest
Deal found 2/20$278
This eDestinos deal was found by Cheapflights users on 2/20. 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 3/2012:20 pmHOU - SJU
1 stop23h 33mMultiple Airlines
Mon 3/245:05 amSJU - HOU
3 stops53h 31mMultiple Airlines
Deal found 2/20$469
This Southwest deal was found by Cheapflights users on 2/18. 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 3/186:30 amHOU - PUJ
1 stop7h 55mSouthwest
Tue 3/252:40 pmPUJ - HOU
1 stop8h 20mSouthwest
Deal found 2/18$480
This Southwest deal was found by Cheapflights users on 2/20. 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.
Fri 3/2810:50 amHOU - MBJ
Nonstop3h 10mSouthwest
Fri 4/42:50 pmMBJ - HOU
Nonstop3h 35mSouthwest
Deal found 2/20$485
This Delta deal was found by Cheapflights users on 2/19. 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 3/196:00 amHOU - PUJ
1 stop6h 10mDelta
Wed 3/262:35 pmPUJ - HOU
1 stop9h 31mDelta
Deal found 2/19$495
This American Airlines deal was found by Cheapflights users on 2/19. 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 5/55:00 amHOU - PUJ
2 stops8h 59mAmerican Airlines
Fri 5/911:49 amPUJ - HOU
1 stop8h 56mAmerican Airlines
Deal found 2/19$499
This American Airlines deal was found by Cheapflights users on 2/19. 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 5/65:00 amHOU - MBJ
1 stop9h 35mAmerican Airlines
Wed 5/1410:53 amMBJ - HOU
1 stop7h 08mAmerican Airlines
Deal found 2/19$505
This Southwest deal was found by Cheapflights users on 2/20. 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 5/65:45 amHOU - PLS
1 stop8h 25mSouthwest
Tue 5/134:05 pmPLS - HOU
1 stop7h 25mSouthwest
Deal found 2/20$514
This American Airlines deal was found by Cheapflights users on 2/20. 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 6/115:00 amHOU - NAS
1 stop6h 26mAmerican Airlines
Wed 6/184:40 pmNAS - HOU
1 stop6h 15mAmerican Airlines
Deal found 2/20$525
This Delta deal was found by Cheapflights users on 2/20. 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.
Tue 4/16:00 amHOU - MBJ
1 stop6h 00mDelta
Sat 4/57:00 amMBJ - HOU
1 stop8h 26mDelta
Deal found 2/20$534

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 February 20, 2025.

Fly from

Hobby

Fly to

Caribbean

Route

Depart

Return

Price

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Mon 3/3

10:15 am-9:00 pm

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Tue 3/11

6:05 am-6:02 pm

1 stop12h 57m

$262

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 3/25

3:05 pm-10:50 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Sat 3/29

6:15 pm-10:20 pm

Nonstop5h 05m

$278

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Wed 3/26

10:41 am-8:10 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Wed 4/2

6:15 am-1:50 pm

1 stop8h 35m

$293

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 3/20

12:20 pm-12:53 pm

1 stop23h 33m

San Juan Luis Munoz Marin Intl

Mon 3/24

5:05 am-9:36 am

3 stops53h 31m

$469

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Tue 3/18

6:30 am-3:25 pm

1 stop7h 55m

Punta Cana

Tue 3/25

2:40 pm-10:00 pm

1 stop8h 20m

$480

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Fri 3/28

10:50 am-2:00 pm

Nonstop3h 10m

Montego Bay Sangster Intl

Fri 4/4

2:50 pm-6:25 pm

Nonstop3h 35m

$485

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Wed 3/19

6:00 am-1:10 pm

1 stop6h 10m

Punta Cana

Wed 3/26

2:35 pm-11:06 pm

1 stop9h 31m

$495

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Mon 5/5

5:00 am-2:59 pm

2 stops8h 59m

Punta Cana

Fri 5/9

11:49 am-7:45 pm

1 stop8h 56m

$499

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Tue 5/6

5:00 am-2:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Wed 5/14

10:53 am-6:01 pm

1 stop7h 08m

$505

HoustonProvidenciales

HOU - PLS

HOUPLS

Houston Hobby

Tue 5/6

5:45 am-3:10 pm

1 stop8h 25m

Providenciales

Tue 5/13

4:05 pm-10:30 pm

1 stop7h 25m

$514

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 57 results
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2
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6

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 $363). 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 February 20, 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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,801 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

British Airways
6.6
Okay
6,762 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $147 and $169, 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 $363). 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$349FlexibilityNo cancel feeOn-time62%
DeltaCheapest$137Average$603FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$140Average$386FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$274Average$682FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$284Average$633FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$413Average$592FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$434Average$678FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$463Average$654FlexibilityNo cancel feeOn-time70%
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