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 73% 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.

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.

$446 Cheap Flights from Hilton Head Island to Caribbean in 2026

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0 bags

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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.

12:11 pm - 10:29 pm

HHH

SJU

10h 18m

1 stop

6:48 am - 3:30 pm

SJU

HHH

8h 42m

1 stop

$446Delta

Wed, Aug 19 - Wed, Aug 26

12:11 pm - 10:29 pm

HHH

SJU

10h 18m

1 stop

6:48 am - 3:30 pm

SJU

HHH

8h 42m

1 stop

$481Delta

Thu, Aug 20 - Wed, Aug 26

12:11 pm - 10:29 pm

HHH

SJU

10h 18m

1 stop

6:48 am - 3:30 pm

SJU

HHH

8h 42m

1 stop

$501Delta

Fri, Aug 21 - Tue, Aug 25

12:11 pm - 10:29 pm

HHH

SJU

10h 18m

1 stop

6:48 am - 3:30 pm

SJU

HHH

8h 42m

1 stop

$526Delta

Sun, Aug 23 - Tue, Aug 25

12:11 pm - 10:29 pm

HHH

SJU

10h 18m

1 stop

6:48 am - 3:30 pm

SJU

HHH

8h 42m

1 stop

$531Delta

Sat, Aug 22 - Wed, Aug 26

2:48 pm - 9:43 am

HHH

SJU

18h 55m

2 stops

4:53 pm - 11:09 am

SJU

HHH

18h 16m

2 stops

$561American Airlines

Sun, Aug 23 - Mon, Aug 24

5:46 pm - 12:48 pm

HHH

SJU

19h 02m

2 stops

7:05 am - 4:38 pm

SJU

HHH

9h 33m

1 stop

$566American Airlines

Thu, Aug 20 - Tue, Aug 25

3:27 pm - 9:43 am

HHH

SJU

18h 16m

2 stops

3:28 pm - 11:09 am

SJU

HHH

19h 41m

2 stops

$571American Airlines

Wed, Aug 19 - Mon, Aug 24

1:45 pm - 2:27 pm

HHH

PUJ

24h 42m

1 stop

2:20 pm - 12:52 pm

PUJ

HHH

22h 32m

2 stops

$792United Airlines

Tue, Sep 29 - Sat, Oct 3

1:45 pm - 11:43 am

HHH

MBJ

22h 58m

1 stop

12:52 pm - 12:59 pm

MBJ

HHH

23h 07m

1 stop

$1,437United Airlines

Sun, Jun 14 - Sun, Jun 21

Delta flights from Hilton Head Island to Caribbean

Our best Delta deals on Hilton Head Island to Caribbean flight tickets

Delta

Aug 19

HHH12:11 pmHilton Head Island

10h 18m

1 stop

SJU10:29 pmSan Juan Luis Munoz Marin Intl

Aug 26

SJU6:48 amSan Juan Luis Munoz Marin Intl

8h 42m

1 stop

HHH3:30 pmHilton Head Island

$446

Delta

Aug 20

HHH12:11 pmHilton Head Island

10h 18m

1 stop

SJU10:29 pmSan Juan Luis Munoz Marin Intl

Aug 26

SJU6:48 amSan Juan Luis Munoz Marin Intl

8h 42m

1 stop

HHH3:30 pmHilton Head Island

$481

Delta

Aug 21

HHH12:11 pmHilton Head Island

10h 18m

1 stop

SJU10:29 pmSan Juan Luis Munoz Marin Intl

Aug 25

SJU6:48 amSan Juan Luis Munoz Marin Intl

8h 42m

1 stop

HHH3:30 pmHilton Head Island

$501

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 23

HHH2:48 pmHilton Head Island

18h 55m

2 stops

SJU9:43 amSan Juan Luis Munoz Marin Intl

Aug 24

SJU4:53 pmSan Juan Luis Munoz Marin Intl

18h 16m

2 stops

HHH11:09 amHilton Head Island

$561

American Airlines

Aug 20

HHH5:46 pmHilton Head Island

19h 02m

2 stops

SJU12:48 pmSan Juan Luis Munoz Marin Intl

Aug 25

SJU7:05 amSan Juan Luis Munoz Marin Intl

9h 33m

1 stop

HHH4:38 pmHilton Head Island

$566

American Airlines

Aug 19

HHH3:27 pmHilton Head Island

18h 16m

2 stops

SJU9:43 amSan Juan Luis Munoz Marin Intl

Aug 24

SJU3:28 pmSan Juan Luis Munoz Marin Intl

19h 41m

2 stops

HHH11:09 amHilton Head Island

$571

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

Quickest round-trip

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Wed 8/19

12:11 pm-10:29 pm

1 stop10h 18m

San Juan Luis Munoz Marin Intl

Wed 8/26

6:48 am-3:30 pm

1 stop8h 42m

$446

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 8/20

12:11 pm-10:29 pm

1 stop10h 18m

San Juan Luis Munoz Marin Intl

Wed 8/26

6:48 am-3:30 pm

1 stop8h 42m

$481

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Fri 8/21

12:11 pm-10:29 pm

1 stop10h 18m

San Juan Luis Munoz Marin Intl

Tue 8/25

6:48 am-3:30 pm

1 stop8h 42m

$501

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sun 8/23

12:11 pm-10:29 pm

1 stop10h 18m

San Juan Luis Munoz Marin Intl

Tue 8/25

6:48 am-3:30 pm

1 stop8h 42m

$526

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sat 8/22

12:11 pm-10:29 pm

1 stop10h 18m

San Juan Luis Munoz Marin Intl

Wed 8/26

6:48 am-3:30 pm

1 stop8h 42m

$531

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sun 8/23

2:48 pm-9:43 am

2 stops18h 55m

San Juan Luis Munoz Marin Intl

Mon 8/24

4:53 pm-11:09 am

2 stops18h 16m

$561

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 8/20

5:46 pm-12:48 pm

2 stops19h 02m

San Juan Luis Munoz Marin Intl

Tue 8/25

7:05 am-4:38 pm

1 stop9h 33m

$566

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Wed 8/19

3:27 pm-9:43 am

2 stops18h 16m

San Juan Luis Munoz Marin Intl

Mon 8/24

3:28 pm-11:09 am

2 stops19h 41m

$571

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Tue 9/29

1:45 pm-2:27 pm

1 stop24h 42m

Punta Cana

Sat 10/3

2:20 pm-12:52 pm

2 stops22h 32m

$792

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Sun 6/14

1:45 pm-11:43 am

1 stop22h 58m

Montego Bay Sangster Intl

Sun 6/21

12:52 pm-12:59 pm

1 stop23h 07m

$1,437

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 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	10h 05m
Direct flights	None

The fastest flight from Hilton Head Island to Caribbean takes 10h 05m

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.