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 73% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 5 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?

United Airlines and American Airlines are the most popular carriers 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.

$439 Cheap Flights from Hilton Head Island to Caribbean Islands in 2026

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.

5:46 pm - 11:42 am

HHH

MBJ

18h 56m

2 stops

12:38 pm - 4:38 pm

MBJ

HHH

27h 00m

1 stop

$597American Airlines

Sun, Aug 9 - Sun, Aug 16

11:47 am - 10:59 pm

HHH

SJU

11h 12m

1 stop

7:14 pm - 2:16 pm

SJU

HHH

19h 02m

2 stops

$606American Airlines

Thu, Jul 9 - Mon, Jul 13

2:48 pm - 1:45 pm

HHH

SJU

22h 57m

2 stops

4:55 pm - 2:03 pm

SJU

HHH

21h 08m

2 stops

$632United Airlines

Mon, Aug 24 - Fri, Aug 28

11:47 am - 10:59 pm

HHH

SJU

11h 12m

1 stop

7:25 am - 4:25 pm

SJU

HHH

9h 00m

1 stop

$641American Airlines

Thu, Jul 9 - Mon, Jul 13

2:58 pm - 1:45 pm

HHH

SJU

22h 47m

2 stops

4:55 pm - 2:03 pm

SJU

HHH

21h 08m

2 stops

$642United Airlines

Mon, Aug 24 - Fri, Aug 28

11:40 am - 11:42 am

HHH

MBJ

25h 02m

2 stops

5:08 pm - 1:17 pm

MBJ

HHH

19h 09m

2 stops

$646American Airlines

Sun, Aug 9 - Sun, Aug 16

2:48 pm - 1:45 pm

HHH

SJU

22h 57m

2 stops

3:56 pm - 2:03 pm

SJU

HHH

22h 07m

1 stop

$649United Airlines

Mon, Aug 24 - Fri, Aug 28

5:46 pm - 11:37 am

HHH

MBJ

18h 51m

1 stop

12:38 pm - 2:57 pm

MBJ

HHH

25h 19m

1 stop

$654American Airlines

Sun, Aug 9 - Sun, Aug 16

2:58 pm - 1:45 pm

HHH

SJU

22h 47m

2 stops

3:56 pm - 2:03 pm

SJU

HHH

22h 07m

1 stop

$659United Airlines

Mon, Aug 24 - Fri, Aug 28

12:15 pm - 10:29 pm

HHH

SJU

10h 14m

1 stop

7:00 am - 3:32 pm

SJU

HHH

8h 32m

1 stop

$885Delta

Thu, Aug 6 - Thu, Aug 13

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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

American Airlines

Aug 9

HHH5:46 pmHilton Head Island

18h 56m

2 stops

MBJ11:42 amMontego Bay Sangster Intl

Aug 16

MBJ12:38 pmMontego Bay Sangster Intl

27h 00m

1 stop

HHH4:38 pmHilton Head Island

$597

American Airlines

Jul 9

HHH11:47 amHilton Head Island

11h 12m

1 stop

SJU10:59 pmSan Juan Luis Munoz Marin Intl

Jul 13

SJU7:14 pmSan Juan Luis Munoz Marin Intl

19h 02m

2 stops

HHH2:16 pmHilton Head Island

$606

American Airlines

Jul 9

HHH11:47 amHilton Head Island

11h 12m

1 stop

SJU10:59 pmSan Juan Luis Munoz Marin Intl

Jul 13

SJU7:25 amSan Juan Luis Munoz Marin Intl

9h 00m

1 stop

HHH4:25 pmHilton Head Island

$641

United Airlines flights from Hilton Head Island to Caribbean Islands

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

United Airlines

Aug 24

HHH2:48 pmHilton Head Island

22h 57m

2 stops

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Aug 28

SJU4:55 pmSan Juan Luis Munoz Marin Intl

21h 08m

2 stops

HHH2:03 pmHilton Head Island

$632

United Airlines

Aug 24

HHH2:58 pmHilton Head Island

22h 47m

2 stops

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Aug 28

SJU4:55 pmSan Juan Luis Munoz Marin Intl

21h 08m

2 stops

HHH2:03 pmHilton Head Island

$642

United Airlines

Aug 24

HHH2:48 pmHilton Head Island

22h 57m

2 stops

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Aug 28

SJU3:56 pmSan Juan Luis Munoz Marin Intl

22h 07m

1 stop

HHH2:03 pmHilton Head Island

$649

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

Cheapest round-trip

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Sun 8/9

5:46 pm-11:42 am

2 stops18h 56m

Montego Bay Sangster Intl

Sun 8/16

12:38 pm-4:38 pm

1 stop27h 00m

$597

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 7/9

11:47 am-10:59 pm

1 stop11h 12m

San Juan Luis Munoz Marin Intl

Mon 7/13

7:14 pm-2:16 pm

2 stops19h 02m

$606

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 8/24

2:48 pm-1:45 pm

2 stops22h 57m

San Juan Luis Munoz Marin Intl

Fri 8/28

4:55 pm-2:03 pm

2 stops21h 08m

$632

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 7/9

11:47 am-10:59 pm

1 stop11h 12m

San Juan Luis Munoz Marin Intl

Mon 7/13

7:25 am-4:25 pm

1 stop9h 00m

$641

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 8/24

2:58 pm-1:45 pm

2 stops22h 47m

San Juan Luis Munoz Marin Intl

Fri 8/28

4:55 pm-2:03 pm

2 stops21h 08m

$642

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Sun 8/9

11:40 am-11:42 am

2 stops25h 02m

Montego Bay Sangster Intl

Sun 8/16

5:08 pm-1:17 pm

2 stops19h 09m

$646

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 8/24

2:48 pm-1:45 pm

2 stops22h 57m

San Juan Luis Munoz Marin Intl

Fri 8/28

3:56 pm-2:03 pm

1 stop22h 07m

$649

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Sun 8/9

5:46 pm-11:37 am

1 stop18h 51m

Montego Bay Sangster Intl

Sun 8/16

12:38 pm-2:57 pm

1 stop25h 19m

$654

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 8/24

2:58 pm-1:45 pm

2 stops22h 47m

San Juan Luis Munoz Marin Intl

Fri 8/28

3:56 pm-2:03 pm

1 stop22h 07m

$659

Quickest round-trip

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 8/6

12:15 pm-10:29 pm

1 stop10h 14m

San Juan Luis Munoz Marin Intl

Thu 8/13

7:00 am-3:32 pm

1 stop8h 32m

$885

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 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 15% 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	21h 15m
Direct flights	None

The fastest flight from Hilton Head Island to Caribbean Islands takes 21h 15m

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

Frequently asked questions about flying 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.
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 (Enhanced Winglets) (27.30% of total bookings). The next most popular plane models are Embraer 175 (12.97%), Embraer 170 (12.70%), and Airbus A220-300 (9.46%).

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.