Caribbean

$123+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SJU
Jul 10 — Jul 171
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Cheap 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 June 10, 2026.

This Southwest deal was found by Cheapflights users on 6/9. 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.
Thu 10/295:05 am
HOU
-
SJU
1 stop10h 25m
Southwest
Thu 10/299:45 pm
SJU
-
HOU
1 stop12h 40m
Southwest
Deal found 6/9$371
This Southwest deal was found by Cheapflights users on 6/9. 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.
Thu 10/295:05 am
HOU
-
SJU
1 stop10h 25m
Southwest
Tue 11/36:45 am
SJU
-
HOU
1 stop14h 05m
Southwest
Deal found 6/9$376
This Southwest deal was found by Cheapflights users on 6/8. 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 7/195:00 am
HOU
-
SXM
1 stop9h 30m
Southwest
Wed 7/223:00 pm
SXM
-
HOU
1 stop9h 15m
Southwest
Deal found 6/8$389
This Southwest deal was found by Cheapflights users on 6/9. 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 8/315:05 am
HOU
-
STT
1 stop7h 45m
Southwest
Fri 9/42:35 pm
STT
-
HOU
2 stops19h 35m
Southwest
Deal found 6/9$402
This Southwest deal was found by Cheapflights users on 6/9. 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.
Wed 7/155:00 am
HOU
-
GCM
1 stop6h 55m
Southwest
Wed 7/2212:50 pm
GCM
-
HOU
1 stop7h 40m
Southwest
Deal found 6/9$406
This Southwest deal was found by Cheapflights users on 6/6. 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 8/215:05 am
HOU
-
SXM
1 stop8h 00m
Southwest
Sun 8/233:05 pm
SXM
-
HOU
1 stop9h 10m
Southwest
Deal found 6/6$415
This Southwest deal was found by Cheapflights users on 6/8. 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 9/145:05 am
HOU
-
AUA
1 stop6h 40m
Southwest
Thu 9/171:45 pm
AUA
-
HOU
1 stop9h 35m
Southwest
Deal found 6/8$421
This Southwest deal was found by Cheapflights users on 6/8. 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 8/156:40 am
HOU
-
SJU
1 stop6h 20m
Southwest
Wed 8/198:20 am
SJU
-
HOU
1 stop9h 35m
Southwest
Deal found 6/8$426
This Southwest deal was found by Cheapflights users on 6/5. 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 7/2712:20 pm
HOU
-
NAS
1 stop5h 15m
Southwest
Thu 7/308:45 am
NAS
-
HOU
1 stop6h 05m
Southwest
Deal found 6/5$435
This Southwest deal was found by Cheapflights users on 6/9. 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 8/315:05 am
HOU
-
STT
1 stop7h 45m
Southwest
Sat 9/52:05 pm
STT
-
HOU
1 stop7h 35m
Southwest
Deal found 6/9$437
This Southwest deal was found by Cheapflights users on 6/8. 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 8/145:05 am
HOU
-
SXM
1 stop8h 00m
Southwest
Mon 8/173:05 pm
SXM
-
HOU
1 stop8h 15m
Southwest
Deal found 6/8$442
This Southwest deal was found by Cheapflights users on 6/6. 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 7/1410:25 am
HOU
-
NAS
1 stop7h 10m
Southwest
Thu 7/162:10 pm
NAS
-
HOU
1 stop7h 55m
Southwest
Deal found 6/6$448

Find flight deals from Hobby to Caribbean

Keep the following information in mind while searching for Hobby to Caribbean flight deals. Data was last updated June 10, 2026.

Round-trip from

$371
(Southwest)

One-way from

$123
(Southwest)

Popular in

June

Cheapest in

October

Average price

$542

Good round-trip deal

$562 or less

Good one-way deal

$298 or less
From Houston Hobby to Caribbean
One-way flight from Houston Hobby to Caribbean
Highest demand for flights based on searches. 12% potential increase in price ($59 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in June 2026
Price to beat on a round-trip flight from Houston Hobby to Caribbean.
Price to beat on a one-way flight from Houston Hobby to Caribbean.

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 June 10, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

HoustonNassau

HOU - NAS

HOUNAS

Houston Hobby

Mon 7/27

12:20 pm-6:35 pm

1 stop5h 15m

Nassau Intl

Thu 7/30

8:45 am-1:50 pm

1 stop6h 05m

$435

HoustonSaint Thomas Island

HOU - STT

HOUSTT

Houston Hobby

Sun 9/13

5:00 am-1:25 pm

1 stop7h 25m

Saint Thomas Island Cyril E King

Sat 9/19

2:05 pm-8:40 pm

1 stop7h 35m

$464

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Sat 6/20

7:10 am-3:05 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 6/24

3:00 pm-11:10 pm

1 stop9h 10m

$468

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Tue 7/28

7:20 pm-12:50 am

Nonstop4h 30m

San Juan Luis Munoz Marin Intl

Thu 7/30

8:15 pm-8:25 am

1 stop13h 10m

$472

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sun 7/5

8:40 pm-10:45 am

1 stop13h 05m

San Juan Luis Munoz Marin Intl

Thu 7/9

10:20 pm-9:35 am

1 stop12h 15m

$476

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Sat 7/11

5:35 pm-1:20 am

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Wed 7/15

8:35 pm-8:25 am

1 stop12h 50m

$476

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Mon 7/6

6:05 pm-1:25 am

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Fri 7/10

10:20 pm-9:40 am

1 stop12h 20m

$476

HoustonGeorge Town

HOU - GCM

HOUGCM

Houston Hobby

Sat 10/31

5:35 pm-12:35 pm

2 stops19h 00m

George Town Owen Roberts Intl

Tue 11/3

1:30 pm-10:50 pm

2 stops10h 20m

$490

HoustonSaint Thomas Island

HOU - STT

HOUSTT

Houston Hobby

Fri 8/28

6:10 pm-1:20 pm

2 stops18h 10m

Saint Thomas Island Cyril E King

Thu 9/3

2:35 pm-8:00 pm

1 stop6h 25m

$499

HoustonNassau

HOU - NAS

HOUNAS

Houston Hobby

Thu 7/9

12:20 pm-6:35 pm

1 stop5h 15m

Nassau Intl

Thu 7/16

8:45 am-3:55 pm

2 stops8h 10m

$504

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/7

Showing 1-10 of 60 resultsSorted by cheapest first
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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.

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, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean (average of $58). Flying from Houston Hobby Airport to Caribbean in December is currently the most expensive (average of $1,198). 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 June 10, 2026.

A simple way to save on the total cost of your ticket is to fly from Houston Hobby Airport to Caribbean at noon. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight in the morning.

How far ahead should I book a flight from Houston Hobby Airport to Caribbean?

The best time to book flights from Houston Hobby Airport to Caribbean is 74 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 June 10, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited 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.

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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.
  • How long is the flight from Houston Hobby Airport to Caribbean?

    A quick flight from Houston Hobby Airport to Caribbean can take about 5h 15m. Southwest provides one of the quickest options available for as low as $435. Houston Hobby Airport and Caribbean are separated by a distance of 1136 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Houston Hobby Airport to Caribbean one-way?

    $72 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 Southwest and Frontier, with prices starting from $72 and $86, respectively.

  • What are the most popular routes 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 $545. While the most popular route (Houston Hobby - San Juan Luis Munoz Marin Intl) can be booked for $302 on average, our data indicates $602 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, January is the cheapest month in which you can book a flight from Houston Hobby Airport to Caribbean (average of $58). Flying from Houston Hobby Airport to Caribbean in December is currently the most expensive (average of $1,198). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 June 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$599FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$165Average$663FlexibilityNo cancel feeOn-time63%
FrontierCheapest$169Average$427FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$170Average$669FlexibilityNo cancel feeOn-time71%
AviancaCheapest$222Average$629FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$675FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$263Average$548FlexibilityNo cancel feeOn-time62%

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