What airlines fly to Caribbean?

American Airlines, Delta and JetBlue are the top three most popular airlines that fly to Caribbean from Hilton Head Island according to our data. American Airlines is the first choice among our users, with 67% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 5 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Hilton Head Island Airport to Caribbean are refreshed on a daily basis.

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

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.

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

The travel and health documents you'll need for your trip to Caribbean 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. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$647 Cheap Flights from Hilton Head Island to Caribbean in 2026/27

Find the cheapest flights from Hilton Head Island to Caribbean

Round-trip

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:17 pm - 1:46 pmHHH Hilton Head Island-PUJ Punta Cana

20h 29m2 stops Charlotte Douglas Miami

2:46 pm - 11:53 amPUJ Punta Cana-HHH Hilton Head Island

22h 07m2 stops Miami Charlotte Douglas

$647American Airlines

Tue, Nov 10 - Tue, Nov 17

5:54 pm - 12:21 pmHHH Hilton Head Island-MBJ Montego Bay Sangster Intl

18h 27m2 stops Charlotte Douglas Miami

6:09 pm - 2:18 pmMBJ Montego Bay Sangster Intl-HHH Hilton Head Island

20h 09m2 stops Miami Charlotte Douglas

$655American Airlines

Thu, Nov 12 - Thu, Nov 19

2:51 pm - 10:15 amHHH Hilton Head Island-MBJ Montego Bay Sangster Intl

19h 24m2 stops Charlotte Douglas Miami

3:32 pm - 2:18 pmMBJ Montego Bay Sangster Intl-HHH Hilton Head Island

22h 46m1 stop Charlotte Douglas

$662American Airlines

Thu, Nov 12 - Thu, Nov 19

11:04 am - 2:28 pmHHH Hilton Head Island-MBJ Montego Bay Sangster Intl

27h 24m1 stop Charlotte Douglas

3:32 pm - 10:36 amMBJ Montego Bay Sangster Intl-HHH Hilton Head Island

19h 04m1 stop Charlotte Douglas

$666American Airlines

Thu, Nov 12 - Thu, Nov 19

4:17 pm - 1:46 pmHHH Hilton Head Island-PUJ Punta Cana

20h 29m2 stops Charlotte Douglas Miami

5:21 pm - 11:53 amPUJ Punta Cana-HHH Hilton Head Island

19h 32m1 stop Charlotte Douglas

$676American Airlines

Tue, Nov 10 - Tue, Nov 17

4:17 pm - 4:21 pmHHH Hilton Head Island-PUJ Punta Cana

23h 04m1 stop Charlotte Douglas

5:21 pm - 11:53 amPUJ Punta Cana-HHH Hilton Head Island

19h 32m1 stop Charlotte Douglas

$826American Airlines

Tue, Nov 10 - Tue, Nov 17

6:22 pm - 2:55 pmHHH Hilton Head Island-PUJ Punta Cana

19h 33m2 stops Charlotte Douglas Miami

5:57 pm - 10:33 amPUJ Punta Cana-HHH Hilton Head Island

17h 36m2 stops Miami Charlotte Douglas

$850American Airlines

Fri, Feb 12 - Wed, Feb 17

6:22 pm - 11:37 amHHH Hilton Head Island-PUJ Punta Cana

16h 15m1 stop Charlotte Douglas

5:57 pm - 10:33 amPUJ Punta Cana-HHH Hilton Head Island

17h 36m2 stops Miami Charlotte Douglas

$850American Airlines

Fri, Feb 12 - Wed, Feb 17

4:17 pm - 1:46 pmHHH Hilton Head Island-PUJ Punta Cana

20h 29m2 stops Charlotte Douglas Miami

12:58 pm - 10:34 amPUJ Punta Cana-HHH Hilton Head Island

22h 36m2 stops Miami Charlotte Douglas

$920American Airlines

Sat, Nov 7 - Sat, Nov 14

4:17 pm - 11:36 amHHH Hilton Head Island-PUJ Punta Cana

18h 19m1 stop Charlotte Douglas

12:58 pm - 10:34 amPUJ Punta Cana-HHH Hilton Head Island

22h 36m2 stops Miami Charlotte Douglas

$927American Airlines

Sat, Nov 7 - Sat, Nov 14

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American Airlines flights from Hilton Head Island to Caribbean

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

American Airlines

Nov 10

HHH4:17 pmHilton Head Island

20h 29m

2 stops

PUJ1:46 pmPunta Cana

Nov 17

PUJ2:46 pmPunta Cana

22h 07m

2 stops

HHH11:53 amHilton Head Island

$647

American Airlines

Nov 12

HHH5:54 pmHilton Head Island

18h 27m

2 stops

MBJ12:21 pmMontego Bay Sangster Intl

Nov 19

MBJ6:09 pmMontego Bay Sangster Intl

20h 09m

2 stops

HHH2:18 pmHilton Head Island

$655

American Airlines

Nov 12

HHH2:51 pmHilton Head Island

19h 24m

2 stops

MBJ10:15 amMontego Bay Sangster Intl

Nov 19

MBJ3:32 pmMontego Bay Sangster Intl

22h 46m

1 stop

HHH2:18 pmHilton Head Island

$662

United Airlines flights from Hilton Head Island to Caribbean

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

United Airlines

Oct 7

HHH1:20 pmHilton Head Island

25h 07m

1 stop

PUJ2:27 pmPunta Cana

Oct 11

PUJ3:35 pmPunta Cana

21h 00m

2 stops

HHH12:35 pmHilton Head Island

$1,301

United Airlines

Oct 7

HHH1:20 pmHilton Head Island

26h 10m

1 stop

PUJ3:30 pmPunta Cana

Oct 11

PUJ3:35 pmPunta Cana

21h 00m

2 stops

HHH12:35 pmHilton Head Island

$1,400

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Hilton Head IslandPunta Cana

HHH Hilton Head Island - PUJ Punta Cana

HHHPUJ

Hilton Head Island

Tue 11/10

4:17 pm-1:46 pm

2 stops20h 29m

Punta Cana

Tue 11/17

2:46 pm-11:53 am

2 stops22h 07m

$647

Hilton Head IslandMontego Bay

HHH Hilton Head Island - MBJ Montego Bay Sangster Intl

HHHMBJ

Hilton Head Island

Thu 11/12

5:54 pm-12:21 pm

2 stops18h 27m

Montego Bay Sangster Intl

Thu 11/19

6:09 pm-2:18 pm

2 stops20h 09m

$655

Hilton Head IslandMontego Bay

HHH Hilton Head Island - MBJ Montego Bay Sangster Intl

HHHMBJ

Hilton Head Island

Thu 11/12

2:51 pm-10:15 am

2 stops19h 24m

Montego Bay Sangster Intl

Thu 11/19

3:32 pm-2:18 pm

1 stop22h 46m

$662

Hilton Head IslandMontego Bay

HHH Hilton Head Island - MBJ Montego Bay Sangster Intl

HHHMBJ

Hilton Head Island

Thu 11/12

11:04 am-2:28 pm

1 stop27h 24m

Montego Bay Sangster Intl

Thu 11/19

3:32 pm-10:36 am

1 stop19h 04m

$666

Hilton Head IslandPunta Cana

HHH Hilton Head Island - PUJ Punta Cana

HHHPUJ

Hilton Head Island

Tue 11/10

4:17 pm-1:46 pm

2 stops20h 29m

Punta Cana

Tue 11/17

5:21 pm-11:53 am

1 stop19h 32m

$676

Hilton Head IslandPunta Cana

HHH Hilton Head Island - PUJ Punta Cana

HHHPUJ

Hilton Head Island

Tue 11/10

4:17 pm-4:21 pm

1 stop23h 04m

Punta Cana

Tue 11/17

5:21 pm-11:53 am

1 stop19h 32m

$826

Hilton Head IslandPunta Cana

HHH Hilton Head Island - PUJ Punta Cana

HHHPUJ

Hilton Head Island

Fri 2/12

6:22 pm-2:55 pm

2 stops19h 33m

Punta Cana

Wed 2/17

5:57 pm-10:33 am

2 stops17h 36m

$850

Quickest round-trip

Hilton Head IslandPunta Cana

HHH Hilton Head Island - PUJ Punta Cana

HHHPUJ

Hilton Head Island

Fri 2/12

6:22 pm-11:37 am

1 stop16h 15m

Punta Cana

Wed 2/17

5:57 pm-10:33 am

2 stops17h 36m

$850

Hilton Head IslandPunta Cana

HHH Hilton Head Island - PUJ Punta Cana

HHHPUJ

Hilton Head Island

Sat 11/7

4:17 pm-1:46 pm

2 stops20h 29m

Punta Cana

Sat 11/14

12:58 pm-10:34 am

2 stops22h 36m

$920

Hilton Head IslandPunta Cana

HHH Hilton Head Island - PUJ Punta Cana

HHHPUJ

Hilton Head Island

Sat 11/7

4:17 pm-11:36 am

1 stop18h 19m

Punta Cana

Sat 11/14

12:58 pm-10:34 am

2 stops22h 36m

$927

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

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 flights?

You could potentially save up to 32% on your flight if you consider stops on a Hilton Head Island to Caribbean flight.

Cheap Hilton Head Island to Caribbean flight deals and tips

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

Best Price Found	$647
Fastest flight time	10h 30m
Direct flights	None

The best flight deal from Hilton Head Island to Caribbean found on momondo in the last 72 hours is $647

The fastest flight from Hilton Head Island to Caribbean takes 10h 30m

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

Search flight deals

Frequently asked questions about flying from Hilton Head Island to Caribbean

When did momondo last update prices for flights from Hilton Head Island Airport to Caribbean?
Prices for flights from Hilton Head Island Airport to Caribbean are refreshed on a daily basis.
How old do you have to be to fly from Hilton Head Island Airport to Caribbean?
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.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean 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. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Why use momondo?

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

It is quick and easy to find Hilton Head Island to Caribbean flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Caribbean that suits you.

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

Yes. momondo allows you to filter the results for Hilton Head Island to Caribbean flights to just show those with flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Hilton Head Island to Caribbean.

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

If you are simply researching potential flights to Caribbean, momondo offers a useful price alert feature which will track prices for flights to Caribbean from Hilton Head Island and alert you when they change.