$137 Find Cheap Flights from Houston Hobby Airport to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hobby to Caribbean Islands departing on 8/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hobby to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$524
Santo Domingo
Santo Domingo2 stops$625
Montego Bay
Montego Bay2 stops$513
Oranjestad
Oranjestad2 stops$562
Santiago de los Caballeros
Santiago de los Caballeros2 stops$625
Nassau
Nassau1 stop$382
Saint Thomas Island
Saint Thomas Island2 stops$524
Kingston
Kingston2 stops$473
Simpson Bay
Simpson Bay1 stop$472
Providenciales
Providenciales2 stops$528
Port of Spain
Port of Spain2 stops$674
Bridgetown
Bridgetown2 stops$697
George Town
George Town1 stop$499
Willemstad
Willemstad2 stops$703
St. John's
St. John's2 stops$715
Puerto Plata
Puerto Plata2 stops$635
Punta Cana
Punta Cana2 stops$524
Santo Domingo
Santo Domingo2 stops$625
Montego Bay
Montego Bay2 stops$513
Oranjestad
Oranjestad2 stops$562
Santiago de los Caballeros
Santiago de los Caballeros2 stops$625
Nassau
Nassau1 stop$382
Saint Thomas Island
Saint Thomas Island2 stops$524
Kingston
Kingston2 stops$473
Simpson Bay
Simpson Bay1 stop$472
Providenciales
Providenciales2 stops$528
Port of Spain
Port of Spain2 stops$674
Bridgetown
Bridgetown2 stops$697
George Town
George Town1 stop$499
Willemstad
Willemstad2 stops$703
St. John's
St. John's2 stops$715
Puerto Plata
Puerto Plata2 stops$635

Book Cheap Hobby to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hobby to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hobby to Caribbean Islands

Sun, Sep 20 - Fri, Sep 25
Delta Logo
6:00 am - 4:49 pm
HOU
-
SJU
9h 49m
1 stop
Delta Logo
2:59 pm - 10:39 pm
SJU
-
HOU
8h 40m
1 stop
$376Delta
Tue, Aug 25 - Tue, Sep 1
American Airlines Logo
9:37 am - 9:55 pm
HOU
-
SJU
11h 18m
2 stops
American Airlines Logo
6:00 am - 3:26 pm
SJU
-
HOU
10h 26m
2 stops
$376American Airlines
Thu, Aug 27 - Tue, Sep 1
Southwest Logo
1:15 pm - 11:50 pm
HOU
-
SJU
9h 35m
1 stop
Southwest Logo
8:20 am - 4:55 pm
SJU
-
HOU
9h 35m
1 stop
$376Southwest
Thu, Aug 27 - Sat, Aug 29
Southwest Logo
2:40 pm - 11:50 pm
HOU
-
SJU
8h 10m
2 stops
Southwest Logo
11:45 am - 7:55 pm
SJU
-
HOU
9h 10m
2 stops
$376Southwest
Sun, Aug 23 - Sat, Aug 29
American Airlines Logo
5:41 am - 4:57 pm
HOU
-
SJU
10h 16m
2 stops
American Airlines Logo
6:00 am - 3:26 pm
SJU
-
HOU
10h 26m
2 stops
$376American Airlines
Sat, Sep 19 - Tue, Sep 22
Delta Logo
6:00 am - 4:49 pm
HOU
-
SJU
9h 49m
1 stop
Delta Logo
7:00 am - 4:30 pm
SJU
-
HOU
10h 30m
1 stop
$381Delta
Thu, Sep 3 - Mon, Sep 7
JetBlue Logo
7:10 am - 10:15 pm
HOU
-
SJU
14h 05m
1 stop
JetBlue Logo
10:00 am - 8:00 pm
SJU
-
HOU
11h 00m
1 stop
$540JetBlue
Thu, Sep 3 - Mon, Sep 7
JetBlue Logo
7:10 am - 10:15 pm
HOU
-
SJU
14h 05m
1 stop
JetBlue Logo
10:00 am - 8:00 pm
SJU
-
HOU
11h 00m
1 stop
$540JetBlue
Sat, Nov 21 - Sat, Nov 28
WestJet Logo
3:05 pm - 3:40 pm
HOU
-
NAS
23h 35m
2 stops
WestJet Logo
4:50 pm - 4:35 pm
NAS
-
HOU
24h 45m
2 stops
$1,691WestJet
Sun, Oct 4 - Sat, Oct 10
WestJet Logo
5:20 pm - 11:10 am
HOU
-
NAS
40h 50m
2 stops
WestJet Logo
12:00 pm - 11:03 pm
NAS
-
HOU
12h 03m
2 stops
$1,695WestJet
Booking Insights

KAYAK's insights & trends for Hobby to Caribbean Islands flights

Get data-powered insights and trends into flights from Hobby to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Houston Hobby Airport found in the last 5 days was to San Juan, at $596 round-trip. The most popular route is from Houston Hobby Airport (HOU) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $795.

What is the cheapest time of day to fly to Caribbean Islands?

The average price for all round-trip flights from Houston Hobby Airport to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $579 on average. Morning departures are around 1% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $588.

Can I save money by flying with a layover from Houston Hobby Airport to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $428, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Houston Hobby Airport to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Houston Hobby Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Houston Hobby Airport to Caribbean Islands is October, when tickets cost $514 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $755 and $735 respectively.

What’s the cheapest day of the week to fly from Houston Hobby Airport to Caribbean Islands?

The average price of all round-trip flights from Houston Hobby Airport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Houston Hobby Airport to Caribbean Islands, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean Islands, Thursday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Houston Hobby Airport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Houston Hobby Airport to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Find deals

Good to know

Low season

January

Cheapest flight

$137
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Houston Hobby Airport to Nassau

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Houston Hobby Airport to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Houston Hobby Airport to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Houston Hobby Airport to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Houston Hobby Airport to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Houston Hobby Airport to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Houston Hobby Airport to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Houston Hobby Airport to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Houston Hobby Airport to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Houston Hobby Airport (HOU)