What airlines fly to Caribbean Islands?

American Airlines, Delta and JetBlue are the top three most popular airlines that fly to Caribbean Islands from Hilton Head Island according to our data. American Airlines is the first choice among our users, with 75% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Hilton Head Island to Caribbean Islands?

American Airlines is the most popular carrier operating from Hilton Head Island to Caribbean Islands

When did momondo last update prices for flights from Hilton Head Island Airport to Caribbean Islands?

Prices for flights from Hilton Head Island Airport to Caribbean Islands are updated daily.

How old do you have to be to fly from Hilton Head Island 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 Hilton Head Island Airport to Caribbean Islands.

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

The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$309 Cheap Flights from Hilton Head Island to Caribbean Islands in 2025/26

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Find the cheapest flights from Hilton Head Island to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:54 pm - 11:54 am

HHH

PUJ

22h 00m2 stops

6:02 pm - 2:59 pm

PUJ

HHH

21h 57m2 stops

$530American Airlines

Sat, Jan 24 - Sat, Jan 31

3:29 pm - 12:55 pm

HHH

PUJ

20h 26m1 stop

6:02 pm - 12:20 pm

PUJ

HHH

19h 18m2 stops

$537American Airlines

Sat, Jan 24 - Sat, Jan 31

3:29 pm - 11:33 am

HHH

MBJ

20h 04m1 stop

1:58 pm - 12:20 pm

MBJ

HHH

22h 22m2 stops

$598American Airlines

Wed, Feb 4 - Sun, Feb 8

3:29 pm - 11:33 am

HHH

MBJ

20h 04m1 stop

12:33 pm - 2:59 pm

MBJ

HHH

26h 26m1 stop

$601American Airlines

Wed, Feb 4 - Sun, Feb 8

3:29 pm - 12:58 pm

HHH

MBJ

21h 29m2 stops

1:58 pm - 12:20 pm

MBJ

HHH

22h 22m2 stops

$610American Airlines

Wed, Feb 4 - Sun, Feb 8

12:51 pm - 12:58 pm

HHH

MBJ

24h 07m2 stops

12:33 pm - 2:59 pm

MBJ

HHH

26h 26m1 stop

$617American Airlines

Wed, Feb 4 - Sun, Feb 8

3:29 pm - 1:34 pm

HHH

MBJ

22h 05m1 stop

2:34 pm - 2:59 pm

MBJ

HHH

24h 25m1 stop

$640American Airlines

Wed, Feb 4 - Sun, Feb 8

4:00 pm - 11:50 pm

HHH

SJU

7h 50m1 stop

1:00 am - 2:01 pm

SJU

HHH

13h 01m2 stops

$817United Airlines

Tue, Apr 28 - Thu, Apr 30

3:29 pm - 4:33 pm

HHH

PUJ

24h 04m1 stop

4:31 pm - 12:20 pm

PUJ

HHH

20h 49m1 stop

$829American Airlines

Sat, Jan 24 - Sat, Jan 31

American Airlines flights from Hilton Head Island to Caribbean Islands

Our best American Airlines deals on Hilton Head Island to Caribbean Islands flight tickets

American Airlines

Jan 24

HHH12:54 pmHilton Head Island

22h 00m

2 stops

PUJ11:54 amPunta Cana

Jan 31

PUJ6:02 pmPunta Cana

21h 57m

2 stops

HHH2:59 pmHilton Head Island

$530

Find similar

American Airlines

Jan 24

HHH3:29 pmHilton Head Island

20h 26m

1 stop

PUJ12:55 pmPunta Cana

Jan 31

PUJ6:02 pmPunta Cana

19h 18m

2 stops

HHH12:20 pmHilton Head Island

$537

Find similar

American Airlines

Feb 4

HHH3:29 pmHilton Head Island

20h 04m

1 stop

MBJ11:33 amMontego Bay Sangster Intl

Feb 8

MBJ1:58 pmMontego Bay Sangster Intl

22h 22m

2 stops

HHH12:20 pmHilton Head Island

$598

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Hilton Head Island to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Sat 1/24

12:54 pm-11:54 am

2 stops22h 00m

Punta Cana

Sat 1/31

6:02 pm-2:59 pm

2 stops21h 57m

$530

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Sat 1/24

3:29 pm-12:55 pm

1 stop20h 26m

Punta Cana

Sat 1/31

6:02 pm-12:20 pm

2 stops19h 18m

$537

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 2/4

3:29 pm-11:33 am

1 stop20h 04m

Montego Bay Sangster Intl

Sun 2/8

1:58 pm-12:20 pm

2 stops22h 22m

$598

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 2/4

3:29 pm-11:33 am

1 stop20h 04m

Montego Bay Sangster Intl

Sun 2/8

12:33 pm-2:59 pm

1 stop26h 26m

$601

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 2/4

3:29 pm-12:58 pm

2 stops21h 29m

Montego Bay Sangster Intl

Sun 2/8

1:58 pm-12:20 pm

2 stops22h 22m

$610

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 2/4

12:51 pm-12:58 pm

2 stops24h 07m

Montego Bay Sangster Intl

Sun 2/8

12:33 pm-2:59 pm

1 stop26h 26m

$617

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 2/4

3:29 pm-1:34 pm

1 stop22h 05m

Montego Bay Sangster Intl

Sun 2/8

2:34 pm-2:59 pm

1 stop24h 25m

$640

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 4/28

4:00 pm-11:50 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Thu 4/30

1:00 am-2:01 pm

2 stops13h 01m

$817

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Sat 1/24

3:29 pm-4:33 pm

1 stop24h 04m

Punta Cana

Sat 1/31

4:31 pm-12:20 pm

1 stop20h 49m

$829

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 12/29

6:13 pm-1:41 pm

2 stops18h 28m

$309

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first

How to get the cheapest flight ticket from Hilton Head Island 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

Prices

Airlines

Can stopping save me money on Hilton Head Island to Caribbean Islands flights?

You could potentially save up to 27% on your flight if you consider stops on a Hilton Head Island to Caribbean Islands flight.

Cheap Hilton Head Island to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hilton Head Island to Caribbean Islands

Fastest flight time	6h 19m
Direct flights	None

The fastest flight from Hilton Head Island to Caribbean Islands takes 6h 19m

There are no direct flights from Hilton Head Island to Caribbean Islands. There are no popular flight routes from Hilton Head Island to Caribbean Islands.

Search flight deals

When did momondo last update prices for flights from Hilton Head Island Airport to Caribbean Islands?
Prices for flights from Hilton Head Island Airport to Caribbean Islands are updated daily.
How old do you have to be to fly from Hilton Head Island 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 Hilton Head Island Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Hilton Head Island to Caribbean Islands?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Hilton Head Island to Caribbean Islands is Embraer 175 (14.84% of total bookings). The next most popular plane models are Airbus A220-300 (13.19%), Embraer 170 (9.89%), and Canadair (Bombardier) Regional Jet 900 (7.14%).

Why use momondo?

Why should I use momondo to find a flight deal from Hilton Head Island to Caribbean Islands?

Finding the right flight to Caribbean Islands from Hilton Head Island is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean Islands quick and easy, saving you time and money.

Can I find flights from Hilton Head Island to Caribbean Islands with flexible booking policies on momondo?

momondo does allow users to show only those flights to Caribbean Islands from Hilton Head Island which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Hilton Head Island to Caribbean Islands?

Once all potential Hilton Head Island to Caribbean Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes momondo offers price alerts on flights to Caribbean Islands from Hilton Head Island. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Caribbean Islands trip

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Popular cities in Caribbean Islands

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Cheap flights from Hilton Head Island to Caribbean Islands from $309

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Big names and deals

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Find the cheapest flights from Hilton Head Island to Caribbean Islands

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American Airlines flights from Hilton Head Island to Caribbean Islands

Our best American Airlines deals on Hilton Head Island to Caribbean Islands flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Hilton Head Island to Caribbean Islands that are best for you.

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Hilton Head Island to Caribbean Islands

Can stopping save me money on Hilton Head Island to Caribbean Islands flights?

You could potentially save up to 27% on your flight if you consider stops on a Hilton Head Island to Caribbean Islands flight.

What is the cheapest airline that flies from Hilton Head Island to Caribbean Islands?

American Airlines is the most popular carrier operating from Hilton Head Island to Caribbean Islands

What airlines fly to Caribbean Islands?

Cheap Hilton Head Island to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hilton Head Island to Caribbean Islands

Fastest flight time

Direct flights

When did momondo last update prices for flights from Hilton Head Island Airport to Caribbean Islands?

How old do you have to be to fly from Hilton Head Island Airport to Caribbean Islands?

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

What is the most popular plane model from Hilton Head Island to Caribbean Islands?

Why use momondo?

Why should I use momondo to find a flight deal from Hilton Head Island to Caribbean Islands?

Can I find flights from Hilton Head Island to Caribbean Islands with flexible booking policies on momondo?

How can momondo help me find flights from Hilton Head Island to Caribbean Islands?

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

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo