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Cheap flights from Houston Hobby Airport to Caribbean Islands from $183

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Houston Hobby Airport to Caribbean Islands departing on 8/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Houston Hobby Airport to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
10:00 am - 10:50 pm
HOU
-
SJU
11h 50m
2 stops
Southwest Logo
5:15 am - 1:50 pm
SJU
-
HOU
9h 35m
2 stops
$376Southwest
Thu, Aug 13 - Wed, Aug 19
Southwest Logo
10:25 am - 6:35 pm
HOU
-
NAS
7h 10m
1 stop
Southwest Logo
8:45 am - 6:15 pm
NAS
-
HOU
10h 30m
1 stop
$415Southwest
Wed, Jul 29 - Mon, Aug 3
Southwest Logo
10:25 am - 6:35 pm
HOU
-
NAS
7h 10m
2 stops
Southwest Logo
8:45 am - 6:15 pm
NAS
-
HOU
10h 30m
1 stop
$419Southwest
Wed, Jul 29 - Mon, Aug 3
Southwest Logo
10:00 am - 10:50 pm
HOU
-
SJU
11h 50m
2 stops
Southwest Logo
8:20 am - 4:55 pm
SJU
-
HOU
9h 35m
1 stop
$421Southwest
Fri, Aug 14 - Wed, Aug 19
Southwest Logo
6:25 am - 12:15 pm
HOU
-
NAS
4h 50m
1 stop
Southwest Logo
1:10 pm - 8:00 pm
NAS
-
HOU
7h 50m
1 stop
$425Southwest
Tue, Aug 18 - Fri, Aug 21
Delta Logo
1:13 pm - 10:29 pm
HOU
-
SJU
8h 16m
1 stop
Delta Logo
2:59 pm - 9:23 pm
SJU
-
HOU
7h 24m
1 stop
$466Delta
Fri, Aug 21 - Sat, Aug 29
Delta Logo
6:00 am - 12:00 pm
HOU
-
MBJ
6h 00m
1 stop
Delta Logo
1:25 pm - 10:35 pm
MBJ
-
HOU
9h 10m
1 stop
$500Delta
Sun, Sep 13 - Wed, Sep 23
American Airlines Logo
8:20 pm - 12:55 pm
HOU
-
MBJ
15h 35m
2 stops
American Airlines Logo
4:02 pm - 11:57 pm
MBJ
-
HOU
8h 55m
1 stop
$505American Airlines
Thu, Nov 5 - Wed, Nov 11
American Airlines Logo
8:22 pm - 4:17 pm
HOU
-
MBJ
19h 55m
1 stop
American Airlines Logo
12:47 pm - 7:51 pm
MBJ
-
HOU
7h 04m
1 stop
$507American Airlines
Thu, Oct 15 - Tue, Oct 20
JetBlue Logo
6:00 am - 1:25 pm
HOU
-
PUJ
6h 25m
1 stop
JetBlue Logo
2:50 pm - 9:51 pm
PUJ
-
HOU
8h 01m
1 stop
$592JetBlue
Mon, Jul 6 - Fri, Jul 10

American Airlines flights from Houston Hobby Airport to Caribbean Islands

Our best American Airlines deals on Houston Hobby Airport to Caribbean Islands flight tickets
American Airlines
Nov 5
HOU8:20 pmHouston Hobby
15h 35m
2 stops
MBJ12:55 pmMontego Bay Sangster Intl
Nov 11
MBJ4:02 pmMontego Bay Sangster Intl
8h 55m
1 stop
HOU11:57 pmHouston Hobby
$505
American Airlines
Oct 15
HOU8:22 pmHouston Hobby
19h 55m
1 stop
MBJ4:17 pmMontego Bay Sangster Intl
Oct 20
MBJ12:47 pmMontego Bay Sangster Intl
7h 04m
1 stop
HOU7:51 pmHouston Hobby
$507
American Airlines
Sep 18
HOU6:19 pmHouston Hobby
18h 34m
2 stops
MBJ12:53 pmMontego Bay Sangster Intl
Sep 28
MBJ12:05 pmMontego Bay Sangster Intl
20h 51m
1 stop
HOU8:56 amHouston Hobby
$512

Southwest flights from Houston Hobby Airport to Caribbean Islands

Our best Southwest deals on Houston Hobby Airport to Caribbean Islands flight tickets
Southwest
Aug 13
HOU10:00 amHouston Hobby
11h 50m
2 stops
SJU10:50 pmSan Juan Luis Munoz Marin Intl
Aug 19
SJU5:15 amSan Juan Luis Munoz Marin Intl
9h 35m
2 stops
HOU1:50 pmHouston Hobby
$376
Southwest
Jul 29
HOU10:25 amHouston Hobby
7h 10m
1 stop
NAS6:35 pmNassau Intl
Aug 3
NAS8:45 amNassau Intl
10h 30m
1 stop
HOU6:15 pmHouston Hobby
$415
Southwest
Jul 29
HOU10:25 amHouston Hobby
7h 10m
2 stops
NAS6:35 pmNassau Intl
Aug 3
NAS8:45 amNassau Intl
10h 30m
1 stop
HOU6:15 pmHouston Hobby
$419

momondo Fare Finder

 
Customize your flight search to find flights from Houston Hobby Airport to Caribbean Islands 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, momondo users made 832,500 searches. Data last updated May 31, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Thu 8/13

10:00 am-10:50 pm

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Wed 8/19

5:15 am-1:50 pm

2 stops9h 35m

$376

HoustonNassau

HOU - NAS

HOUNAS

Houston Hobby

Wed 7/29

10:25 am-6:35 pm

1 stop7h 10m

Nassau Intl

Mon 8/3

8:45 am-6:15 pm

1 stop10h 30m

$415

HoustonNassau

HOU - NAS

HOUNAS

Houston Hobby

Wed 7/29

10:25 am-6:35 pm

2 stops7h 10m

Nassau Intl

Mon 8/3

8:45 am-6:15 pm

1 stop10h 30m

$419

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Fri 8/14

10:00 am-10:50 pm

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Wed 8/19

8:20 am-4:55 pm

1 stop9h 35m

$421
Quickest round-trip

HoustonNassau

HOU - NAS

HOUNAS

Houston Hobby

Tue 8/18

6:25 am-12:15 pm

1 stop4h 50m

Nassau Intl

Fri 8/21

1:10 pm-8:00 pm

1 stop7h 50m

$425

HoustonSan Juan

HOU - SJU

HOUSJU

Houston Hobby

Fri 8/21

1:13 pm-10:29 pm

1 stop8h 16m

San Juan Luis Munoz Marin Intl

Sat 8/29

2:59 pm-9:23 pm

1 stop7h 24m

$466

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Sun 9/13

6:00 am-12:00 pm

1 stop6h 00m

Montego Bay Sangster Intl

Wed 9/23

1:25 pm-10:35 pm

1 stop9h 10m

$500

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Thu 11/5

8:20 pm-12:55 pm

2 stops15h 35m

Montego Bay Sangster Intl

Wed 11/11

4:02 pm-11:57 pm

1 stop8h 55m

$505

HoustonMontego Bay

HOU - MBJ

HOUMBJ

Houston Hobby

Thu 10/15

8:22 pm-4:17 pm

1 stop19h 55m

Montego Bay Sangster Intl

Tue 10/20

12:47 pm-7:51 pm

1 stop7h 04m

$507

HoustonPunta Cana

HOU - PUJ

HOUPUJ

Houston Hobby

Mon 7/6

6:00 am-1:25 pm

1 stop6h 25m

Punta Cana

Fri 7/10

2:50 pm-9:51 pm

1 stop8h 01m

$592

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Houston Hobby Airport to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Houston Hobby Airport, with most prices found around $82. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Houston Hobby Airport averaging around $94.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Houston Hobby Airport to Caribbean Islands is on a Sunday. Travelers who choose to depart for Caribbean Islands on a Sunday will often find tickets for as low as $506. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $571. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is at noon. momondo users have found flights departing from Houston Hobby Airport to Caribbean Islands at noon for as low as $394. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the evening because they tend to be around $541. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Houston Hobby to Caribbean Islands flight route?

Fly from Houston Hobby to Punta Cana for the best Houston Hobby - Caribbean Islands flight prices

How far in advance should I book a flight from Houston Hobby Airport to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Houston Hobby Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $410 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Houston Hobby Airport for as low as $327 on momondo.

What cabin class options are available on Houston Hobby Airport to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Houston Hobby Airport to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Houston Hobby Airport to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Houston Hobby Airport to Caribbean Islands.

Cheap Houston Hobby Airport to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Houston Hobby Airport to Caribbean Islands

Fastest flight time

2h 54m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Houston Hobby Airport to Caribbean Islands takes 2h 54m
Direct flights go from Houston Hobby Airport to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Houston Hobby Airport there are direct flights to Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), San Juan Luis Munoz Marin Intl (SJU).
Search flight deals

Frequently asked questions about flying from Houston Hobby Airport to Caribbean Islands

  • When did momondo last update prices for flights from Houston Hobby Airport to Caribbean Islands?

    Prices for flights from Houston Hobby Airport to Caribbean Islands are refreshed on a daily basis.

  • How many operators does momondo search for flights from Houston Hobby Airport to Caribbean Islands?

  • How old do you have to be to fly from Houston Hobby Airport to Caribbean Islands?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Houston Hobby Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Houston Hobby Airport to Caribbean Islands?

Best airlines flying from Houston Hobby Airport to Caribbean Islands

Compare and see reviews for airlines that fly from Houston Hobby Airport to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $101Free CancellationRating
6.2
Search Spirit Airlines flights
DeltaPriceFrom $108Free CancellationRating
7.9
8,410 reviews
Search Delta flights
SouthwestPriceFrom $165Free CancellationRating
8.0
4,257 reviews
Search Southwest flights
FrontierPriceFrom $168Free CancellationRating
5.6
2,925 reviews
Search Frontier flights
American AirlinesPriceFrom $170Free CancellationRating
7.1
11,645 reviews
Search American Airlines flights
AviancaPriceFrom $222Free CancellationRating
6.5
2,527 reviews
Search Avianca flights
United AirlinesPriceFrom $244Free CancellationRating
7.4
9,769 reviews
Search United Airlines flights
JetBluePriceFrom $337Free CancellationRating
7.1
2,985 reviews
Search JetBlue flights

Why use momondo?

Why should I use momondo to find a flight deal from Houston to Caribbean Islands?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean Islands from Houston.

Can I find flights from Houston to Caribbean Islands with flexible booking policies on momondo?

All flight searches from Houston to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Houston to Caribbean Islands?

momondo helps you find the best flight between Houston and Caribbean Islands by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Houston to Caribbean Islands right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Houston to Caribbean Islands flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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