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 71% 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.

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.

$358 Cheap Flights from Hilton Head Island to Caribbean in 2026

Find the cheapest flights from Hilton Head Island to Caribbean

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:27 pm - 9:43 am

HHH

SJU

18h 16m

2 stops

7:20 pm - 11:09 am

SJU

HHH

15h 49m

2 stops

$566American Airlines

Sat, Aug 29 - Sat, Sep 5

3:29 pm - 2:10 pm

HHH

GGT

22h 41m

2 stops

2:50 pm - 12:20 pm

GGT

HHH

21h 30m

2 stops

$568American Airlines

Fri, Jan 8 - Tue, Jan 12

3:29 pm - 2:10 pm

HHH

GGT

22h 41m

2 stops

2:00 pm - 2:59 pm

GGT

HHH

24h 59m

1 stop

$576American Airlines

Fri, Jan 8 - Tue, Jan 12

2:48 pm - 11:43 am

HHH

MBJ

21h 55m

2 stops

2:40 pm - 2:03 pm

MBJ

HHH

22h 23m

2 stops

$587United Airlines

Sat, Sep 12 - Sat, Sep 19

1:45 pm - 11:43 am

HHH

MBJ

22h 58m

1 stop

12:52 pm - 2:03 pm

MBJ

HHH

24h 11m

2 stops

$596United Airlines

Tue, Sep 15 - Tue, Sep 22

12:51 pm - 1:58 pm

HHH

CUR

24h 07m

1 stop

3:47 pm - 12:20 pm

CUR

HHH

21h 33m

2 stops

$600American Airlines

Sat, Jan 23 - Thu, Jan 28

11:40 am - 11:43 pm

HHH

SJU

12h 03m

1 stop

6:45 am - 5:05 pm

SJU

HHH

10h 20m

1 stop

$601American Airlines

Sat, Aug 29 - Sat, Sep 5

1:45 pm - 11:43 am

HHH

MBJ

22h 58m

1 stop

12:52 pm - 12:59 pm

MBJ

HHH

23h 07m

1 stop

$601United Airlines

Tue, Sep 15 - Tue, Sep 22

3:29 pm - 1:58 pm

HHH

CUR

21h 29m

1 stop

3:32 pm - 12:20 pm

CUR

HHH

21h 48m

1 stop

$603American Airlines

Sat, Jan 23 - Thu, Jan 28

12:51 pm - 4:45 pm

HHH

CUR

26h 54m

2 stops

5:45 pm - 2:59 pm

CUR

HHH

22h 14m

2 stops

$611American Airlines

Sat, Jan 23 - Thu, Jan 28

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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

Aug 29

HHH3:27 pmHilton Head Island

18h 16m

2 stops

SJU9:43 amSan Juan Luis Munoz Marin Intl

Sep 5

SJU7:20 pmSan Juan Luis Munoz Marin Intl

15h 49m

2 stops

HHH11:09 amHilton Head Island

$566

American Airlines

Jan 8

HHH3:29 pmHilton Head Island

22h 41m

2 stops

GGT2:10 pmGeorgetown Exuma Intl

Jan 12

GGT2:50 pmGeorgetown Exuma Intl

21h 30m

2 stops

HHH12:20 pmHilton Head Island

$568

American Airlines

Jan 8

HHH3:29 pmHilton Head Island

22h 41m

2 stops

GGT2:10 pmGeorgetown Exuma Intl

Jan 12

GGT2:00 pmGeorgetown Exuma Intl

24h 59m

1 stop

HHH2:59 pmHilton Head Island

$576

United Airlines flights from Hilton Head Island to Caribbean

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

United Airlines

Sep 12

HHH2:48 pmHilton Head Island

21h 55m

2 stops

MBJ11:43 amMontego Bay Sangster Intl

Sep 19

MBJ2:40 pmMontego Bay Sangster Intl

22h 23m

2 stops

HHH2:03 pmHilton Head Island

$587

United Airlines

Sep 15

HHH1:45 pmHilton Head Island

22h 58m

1 stop

MBJ11:43 amMontego Bay Sangster Intl

Sep 22

MBJ12:52 pmMontego Bay Sangster Intl

24h 11m

2 stops

HHH2:03 pmHilton Head Island

$596

United Airlines

Sep 15

HHH1:45 pmHilton Head Island

22h 58m

1 stop

MBJ11:43 amMontego Bay Sangster Intl

Sep 22

MBJ12:52 pmMontego Bay Sangster Intl

23h 07m

1 stop

HHH12:59 pmHilton Head Island

$601

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 IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sat 8/29

3:27 pm-9:43 am

2 stops18h 16m

San Juan Luis Munoz Marin Intl

Sat 9/5

7:20 pm-11:09 am

2 stops15h 49m

$566

Hilton Head IslandGeorgetown

HHH - GGT

HHHGGT

Hilton Head Island

Fri 1/8

3:29 pm-2:10 pm

2 stops22h 41m

Georgetown Exuma Intl

Tue 1/12

2:50 pm-12:20 pm

2 stops21h 30m

$568

Hilton Head IslandGeorgetown

HHH - GGT

HHHGGT

Hilton Head Island

Fri 1/8

3:29 pm-2:10 pm

2 stops22h 41m

Georgetown Exuma Intl

Tue 1/12

2:00 pm-2:59 pm

1 stop24h 59m

$576

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Sat 9/12

2:48 pm-11:43 am

2 stops21h 55m

Montego Bay Sangster Intl

Sat 9/19

2:40 pm-2:03 pm

2 stops22h 23m

$587

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 9/15

1:45 pm-11:43 am

1 stop22h 58m

Montego Bay Sangster Intl

Tue 9/22

12:52 pm-2:03 pm

2 stops24h 11m

$596

Hilton Head IslandWillemstad

HHH - CUR

HHHCUR

Hilton Head Island

Sat 1/23

12:51 pm-1:58 pm

1 stop24h 07m

Willemstad Hato Int.

Thu 1/28

3:47 pm-12:20 pm

2 stops21h 33m

$600

Quickest round-trip

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sat 8/29

11:40 am-11:43 pm

1 stop12h 03m

San Juan Luis Munoz Marin Intl

Sat 9/5

6:45 am-5:05 pm

1 stop10h 20m

$601

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 9/15

1:45 pm-11:43 am

1 stop22h 58m

Montego Bay Sangster Intl

Tue 9/22

12:52 pm-12:59 pm

1 stop23h 07m

$601

Hilton Head IslandWillemstad

HHH - CUR

HHHCUR

Hilton Head Island

Sat 1/23

3:29 pm-1:58 pm

1 stop21h 29m

Willemstad Hato Int.

Thu 1/28

3:32 pm-12:20 pm

1 stop21h 48m

$603

Hilton Head IslandWillemstad

HHH - CUR

HHHCUR

Hilton Head Island

Sat 1/23

12:51 pm-4:45 pm

2 stops26h 54m

Willemstad Hato Int.

Thu 1/28

5:45 pm-2:59 pm

2 stops22h 14m

$611

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 18% 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	15h 24m
Direct flights	None

The fastest flight from Hilton Head Island to Caribbean takes 15h 24m

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.