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 74% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 7 different airlines that fly to Caribbean 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?

American Airlines is the most popular carrier operating 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.

$273 Cheap Flights from Hilton Head Island to Caribbean in 2026

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Find the cheapest flights from Hilton Head Island to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:15 pm - 11:06 am

HHH

PUJ

16h 51m

2 stops

2:20 pm - 11:53 am

PUJ

HHH

21h 33m

2 stops

$613American Airlines

Wed, Mar 11 - Mon, Mar 16

3:00 pm - 3:10 pm

HHH

MBJ

25h 10m

2 stops

4:12 pm - 12:52 pm

MBJ

HHH

19h 40m

2 stops

$630United Airlines

Thu, May 21 - Mon, May 25

5:21 pm - 1:31 pm

HHH

MBJ

21h 10m

1 stop

12:41 pm - 12:26 pm

MBJ

HHH

22h 45m

1 stop

$640American Airlines

Tue, Jun 23 - Sat, Jun 27

5:21 pm - 11:19 am

HHH

MBJ

18h 58m

1 stop

12:30 pm - 11:10 am

MBJ

HHH

21h 40m

1 stop

$646American Airlines

Tue, Jun 23 - Sun, Jun 28

11:40 am - 11:19 am

HHH

MBJ

24h 39m

1 stop

5:17 pm - 12:26 pm

MBJ

HHH

18h 09m

2 stops

$649American Airlines

Tue, Jun 23 - Sat, Jun 27

11:40 am - 11:45 am

HHH

MBJ

25h 05m

2 stops

12:41 pm - 12:26 pm

MBJ

HHH

22h 45m

1 stop

$665American Airlines

Wed, Jun 24 - Sat, Jun 27

5:21 pm - 3:20 pm

HHH

MBJ

22h 59m

1 stop

12:41 pm - 12:26 pm

MBJ

HHH

22h 45m

1 stop

$668American Airlines

Wed, Jun 24 - Sat, Jun 27

11:40 am - 1:28 pm

HHH

MBJ

26h 48m

2 stops

5:17 pm - 11:10 am

MBJ

HHH

16h 53m

2 stops

$669American Airlines

Wed, Jun 24 - Sat, Jun 27

11:40 am - 1:28 pm

HHH

MBJ

26h 48m

2 stops

4:20 pm - 11:10 am

MBJ

HHH

17h 50m

1 stop

$670American Airlines

Wed, Jun 24 - Sun, Jun 28

1:45 pm - 3:10 pm

HHH

MBJ

26h 25m

2 stops

4:12 pm - 2:01 pm

MBJ

HHH

20h 49m

2 stops

$684United Airlines

Thu, Jun 4 - Mon, Jun 8

American Airlines flights from Hilton Head Island to Caribbean

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

American Airlines

Feb 13

HHH2:58 pmHilton Head Island

5h 51m

1 stop

SJU9:49 pmSan Juan Luis Munoz Marin Intl

Mar 19

SJU3:40 pmSan Juan Luis Munoz Marin Intl

18h 53m

2 stops

HHH10:33 amHilton Head Island

$587

American Airlines

Feb 13

HHH6:20 pmHilton Head Island

18h 13m

2 stops

SJU1:33 pmSan Juan Luis Munoz Marin Intl

Mar 19

SJU6:01 pmSan Juan Luis Munoz Marin Intl

16h 32m

2 stops

HHH10:33 amHilton Head Island

$613

American Airlines

Jun 23

HHH5:21 pmHilton Head Island

21h 10m

1 stop

MBJ1:31 pmMontego Bay Sangster Intl

Jun 27

MBJ12:41 pmMontego Bay Sangster Intl

22h 45m

1 stop

HHH12:26 pmHilton Head Island

$640

United Airlines flights from Hilton Head Island to Caribbean

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

United Airlines

May 21

HHH3:00 pmHilton Head Island

25h 10m

2 stops

MBJ3:10 pmMontego Bay Sangster Intl

May 25

MBJ4:12 pmMontego Bay Sangster Intl

19h 40m

2 stops

HHH12:52 pmHilton Head Island

$630

United Airlines

Jun 4

HHH1:45 pmHilton Head Island

26h 25m

2 stops

MBJ3:10 pmMontego Bay Sangster Intl

Jun 8

MBJ4:12 pmMontego Bay Sangster Intl

20h 49m

2 stops

HHH2:01 pmHilton Head Island

$684

United Airlines

Apr 24

HHH4:11 pmHilton Head Island

21h 39m

2 stops

MBJ12:50 pmMontego Bay Sangster Intl

Apr 28

MBJ4:12 pmMontego Bay Sangster Intl

22h 18m

2 stops

HHH3:30 pmHilton Head Island

$693

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

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Wed 3/11

6:15 pm-11:06 am

2 stops16h 51m

Punta Cana

Mon 3/16

2:20 pm-11:53 am

2 stops21h 33m

$613

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Thu 5/21

3:00 pm-3:10 pm

2 stops25h 10m

Montego Bay Sangster Intl

Mon 5/25

4:12 pm-12:52 pm

2 stops19h 40m

$630

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 6/23

5:21 pm-1:31 pm

1 stop21h 10m

Montego Bay Sangster Intl

Sat 6/27

12:41 pm-12:26 pm

1 stop22h 45m

$640

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 6/23

5:21 pm-11:19 am

1 stop18h 58m

Montego Bay Sangster Intl

Sun 6/28

12:30 pm-11:10 am

1 stop21h 40m

$646

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 6/23

11:40 am-11:19 am

1 stop24h 39m

Montego Bay Sangster Intl

Sat 6/27

5:17 pm-12:26 pm

2 stops18h 09m

$649

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 6/24

11:40 am-11:45 am

2 stops25h 05m

Montego Bay Sangster Intl

Sat 6/27

12:41 pm-12:26 pm

1 stop22h 45m

$665

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 6/24

5:21 pm-3:20 pm

1 stop22h 59m

Montego Bay Sangster Intl

Sat 6/27

12:41 pm-12:26 pm

1 stop22h 45m

$668

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 6/24

11:40 am-1:28 pm

2 stops26h 48m

Montego Bay Sangster Intl

Sat 6/27

5:17 pm-11:10 am

2 stops16h 53m

$669

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 6/24

11:40 am-1:28 pm

2 stops26h 48m

Montego Bay Sangster Intl

Sun 6/28

4:20 pm-11:10 am

1 stop17h 50m

$670

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Thu 6/4

1:45 pm-3:10 pm

2 stops26h 25m

Montego Bay Sangster Intl

Mon 6/8

4:12 pm-2:01 pm

2 stops20h 49m

$684

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted 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 3% 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

Fastest flight time	5h 51m
Direct flights	None

The fastest flight from Hilton Head Island to Caribbean takes 5h 51m

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

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.