What is the cheapest airline that flies from Hilton Head Island to Caribbean Islands?

American Airlines is the most popular carrier operating from Hilton Head Island to Caribbean Islands

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

$410 Cheap Flights from Hilton Head Island to Caribbean Islands in 2025/26

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Hilton Head Island to Caribbean Islands

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:17 pm - 10:09 amHHH-SJU

18h 52m2 stops

6:42 pm - 2:57 pmSJU-HHH

21h 15m2 stops

$425American Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

11:02 am - 2:35 pmHHH-SJU

27h 33m2 stops

6:55 pm - 5:36 pmSJU-HHH

22h 41m2 stops

$473American Airlines

Find Deal

Tue, Apr 7 - Wed, Apr 8

2:17 pm - 10:09 amHHH-SJU

18h 52m2 stops

8:20 am - 2:57 pmSJU-HHH

7h 37m1 stop

$485American Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

6:07 pm - 10:35 amHHH-SJU

16h 28m1 stop

6:55 pm - 5:36 pmSJU-HHH

22h 41m2 stops

$514American Airlines

Find Deal

Tue, Apr 7 - Wed, Apr 8

12:21 pm - 10:05 pmHHH-SJU

8h 44m1 stop

8:20 am - 2:57 pmSJU-HHH

7h 37m1 stop

$565American Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

6:25 pm - 12:40 pmHHH-PUJ

18h 15m2 stops

4:45 pm - 10:14 amPUJ-HHH

17h 29m2 stops

$582American Airlines

Find Deal

Mon, Apr 6 - Wed, Apr 8

12:51 pm - 10:10 amHHH-MBJ

21h 19m2 stops

4:16 pm - 12:20 pmMBJ-HHH

20h 04m2 stops

$591American Airlines

Find Deal

Wed, Feb 4 - Sun, Feb 8

11:02 am - 7:45 pmHHH-SJU

8h 43m1 stop

8:30 am - 2:20 pmSJU-HHH

5h 50m1 stop

$595American Airlines

Find Deal

Tue, Apr 7 - Wed, Apr 8

3:00 pm - 3:05 pmHHH-PUJ

24h 05m1 stop

4:35 pm - 1:52 pmPUJ-HHH

21h 17m2 stops

$1,037United Airlines

Find Deal

Mon, Apr 6 - Wed, Apr 8

3:00 pm - 3:05 pmHHH-PUJ

24h 05m1 stop

1:50 pm - 1:52 pmPUJ-HHH

24h 02m1 stop

$1,262United Airlines

Find Deal

Mon, Apr 6 - Wed, Apr 8

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

Dec 4

HHH2:17 pmHilton Head Island

18h 52m

2 stops

SJU10:09 amSan Juan Luis Munoz Marin Intl

Dec 8

SJU6:42 pmSan Juan Luis Munoz Marin Intl

21h 15m

2 stops

HHH2:57 pmHilton Head Island

$425

Find similar

American Airlines

Apr 7

HHH11:02 amHilton Head Island

27h 33m

2 stops

SJU2:35 pmSan Juan Luis Munoz Marin Intl

Apr 8

SJU6:55 pmSan Juan Luis Munoz Marin Intl

22h 41m

2 stops

HHH5:36 pmHilton Head Island

$473

Find similar

American Airlines

Dec 4

HHH2:17 pmHilton Head Island

18h 52m

2 stops

SJU10:09 amSan Juan Luis Munoz Marin Intl

Dec 8

SJU8:20 amSan Juan Luis Munoz Marin Intl

7h 37m

1 stop

HHH2:57 pmHilton Head Island

$485

Find similar

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

Apr 6

HHH3:00 pmHilton Head Island

24h 05m

1 stop

PUJ3:05 pmPunta Cana

Apr 8

PUJ4:35 pmPunta Cana

21h 17m

2 stops

HHH1:52 pmHilton Head Island

$1,037

Find similar

United Airlines

Apr 6

HHH3:00 pmHilton Head Island

24h 05m

1 stop

PUJ3:05 pmPunta Cana

Apr 8

PUJ1:50 pmPunta Cana

24h 02m

1 stop

HHH1:52 pmHilton Head Island

$1,262

Find similar

United Airlines

Apr 6

HHH3:00 pmHilton Head Island

24h 05m

1 stop

PUJ3:05 pmPunta Cana

Apr 8

PUJ1:50 pmPunta Cana

24h 02m

1 stop

HHH1:52 pmHilton Head Island

$1,379

Find similar

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

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 12/4

2:17 pm-10:09 am

2 stops18h 52m

San Juan Luis Munoz Marin Intl

Mon 12/8

6:42 pm-2:57 pm

2 stops21h 15m

$425

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 4/7

11:02 am-2:35 pm

2 stops27h 33m

San Juan Luis Munoz Marin Intl

Wed 4/8

6:55 pm-5:36 pm

2 stops22h 41m

$473

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 12/4

2:17 pm-10:09 am

2 stops18h 52m

San Juan Luis Munoz Marin Intl

Mon 12/8

8:20 am-2:57 pm

1 stop7h 37m

$485

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 4/7

6:07 pm-10:35 am

1 stop16h 28m

San Juan Luis Munoz Marin Intl

Wed 4/8

6:55 pm-5:36 pm

2 stops22h 41m

$514

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 12/4

12:21 pm-10:05 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Mon 12/8

8:20 am-2:57 pm

1 stop7h 37m

$565

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Mon 4/6

6:25 pm-12:40 pm

2 stops18h 15m

Punta Cana

Wed 4/8

4:45 pm-10:14 am

2 stops17h 29m

$582

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 2/4

12:51 pm-10:10 am

2 stops21h 19m

Montego Bay Sangster Intl

Sun 2/8

4:16 pm-12:20 pm

2 stops20h 04m

$591

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 4/7

11:02 am-7:45 pm

1 stop8h 43m

San Juan Luis Munoz Marin Intl

Wed 4/8

8:30 am-2:20 pm

1 stop5h 50m

$595

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Mon 4/6

3:00 pm-3:05 pm

1 stop24h 05m

Punta Cana

Wed 4/8

4:35 pm-1:52 pm

2 stops21h 17m

$1,037

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Mon 4/6

3:00 pm-3:05 pm

1 stop24h 05m

Punta Cana

Wed 4/8

1:50 pm-1:52 pm

1 stop24h 02m

$1,262

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 38% 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

Direct flights	None

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

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 Airbus A220-300 (13.79% of total bookings). The next most popular plane models are Embraer 175 (11.33%), Canadair (Bombardier) Regional Jet 900 (8.37%), and Embraer 175 (Enhanced Winglets) (7.88%).

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.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Thu 12/4

Thu 12/11

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Flights to New Yorkfrom $49

Flights to Londonfrom $313

Flights to Bangkokfrom $507

Flights to Tokyofrom $381

Flights to Los Angelesfrom $49

Flights to Parisfrom $340

Flights to Copenhagenfrom $358

Flights to Istanbulfrom $373

Flights to Manilafrom $521

Flights to Romefrom $321

Flights to Miamifrom $49

Flights to Chicagofrom $54

Cheap flights from Hilton Head Island to Caribbean Islands from $410

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Hilton Head Island to Caribbean Islands

Cheap round-trip flights

Cheap one-way flights

American Airlines flights from Hilton Head Island to Caribbean Islands

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

United Airlines flights from Hilton Head Island to Caribbean Islands

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

momondo Fare Finder

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

See travel insights to Caribbean Islands from

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

Can stopping save me money on Hilton Head Island to Caribbean Islands flights?

You could potentially save up to 38% on your flight if you consider stops on a Hilton Head Island to Caribbean Islands flight.

What is the cheapest airline that flies from Hilton Head Island to Caribbean Islands?

American Airlines is the most popular carrier operating from Hilton Head Island to Caribbean Islands

What airlines fly to Caribbean Islands?

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

Direct flights

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

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

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

What is the most popular plane model from Hilton Head Island to Caribbean Islands?

Why use momondo?

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

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

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

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

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo