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$511+ Cheap flights from Hilton Head Island (HHH) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Caribbean

Keep the following information in mind while searching for Hilton Head Island to Caribbean flight deals. Data was last updated February 20, 2025.

Round-trip from

$511
(American Airlines)
From Hilton Head Island to Caribbean
Search Deals

Find flight deals from Hilton Head Island to Caribbean

Cheapest flights from Hilton Head Island to Caribbean
Explore the most affordable flight options available from Hilton Head Island to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/66:06 pmHHH - MHH
2 stops19h 04mAmerican Airlines
Sun 4/1311:55 amMHH - HHH
2 stops22h 28mAmerican Airlines
Deal found 2/20$511
This American Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/56:06 pmHHH - PUJ
2 stops18h 58mAmerican Airlines
Sat 4/122:05 pmPUJ - HHH
2 stops20h 18mAmerican Airlines
Deal found 2/19$580
This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/62:50 pmHHH - GND
2 stops23h 11mAmerican Airlines
Sun 4/133:01 pmGND - HHH
2 stops23h 19mAmerican Airlines
Deal found 2/20$754
This American Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/282:46 pmHHH - MBJ
2 stops19h 59mAmerican Airlines
Sun 3/163:34 pmMBJ - HHH
2 stops21h 45mAmerican Airlines
Deal found 2/19$768
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/271:15 pmHHH - SJU
1 stop10h 00mDelta
Fri 5/27:15 amSJU - HHH
1 stop9h 26mDelta
Deal found 2/20$805
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/44:18 pmHHH - MBJ
2 stops23h 52mUnited Airlines
Wed 4/94:12 pmMBJ - HHH
2 stops22h 25mUnited Airlines
Deal found 2/20$856
This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/146:06 pmHHH - CUR
2 stops21h 33mAmerican Airlines
Sat 4/194:40 pmCUR - HHH
2 stops21h 40mAmerican Airlines
Deal found 2/20$924
This United deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/274:18 pmHHH - SJU
2 stops46h 03mMultiple Airlines
Fri 5/23:56 pmSJU - HHH
1 stop22h 03mMultiple Airlines
Deal found 2/20$2,069

Find flights from Hilton Head Island to Caribbean within your budget

Customize your flight search to find flights from Hilton Head Island to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Hilton Head Island

Fly to

Caribbean

Route

Depart

Return

Price

Hilton Head IslandMarsh Harbour

HHH - MHH

HHHMHH

Hilton Head Island

Sun 4/6

6:06 pm-1:10 pm

2 stops19h 04m

Marsh Harbour

Sun 4/13

11:55 am-10:23 am

2 stops22h 28m

$511

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Sat 4/5

6:06 pm-1:04 pm

2 stops18h 58m

Punta Cana

Sat 4/12

2:05 pm-10:23 am

2 stops20h 18m

$580

Hilton Head IslandSt. George's

HHH - GND

HHHGND

Hilton Head Island

Sun 4/6

2:50 pm-2:01 pm

2 stops23h 11m

St. George's Point Saline Intl

Sun 4/13

3:01 pm-2:20 pm

2 stops23h 19m

$754

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sun 4/27

1:15 pm-11:15 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Fri 5/2

7:15 am-4:41 pm

1 stop9h 26m

$805

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Fri 4/4

4:18 pm-3:10 pm

2 stops23h 52m

Montego Bay Sangster Intl

Wed 4/9

4:12 pm-3:37 pm

2 stops22h 25m

$856

Hilton Head IslandWillemstad

HHH - CUR

HHHCUR

Hilton Head Island

Mon 4/14

6:06 pm-3:39 pm

2 stops21h 33m

Willemstad Hato Int.

Sat 4/19

4:40 pm-2:20 pm

2 stops21h 40m

$924

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sun 4/27

4:18 pm-2:21 pm

2 stops46h 03m

San Juan Luis Munoz Marin Intl

Fri 5/2

3:56 pm-1:59 pm

1 stop22h 03m

$2,069

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Best time to book a flight from Hilton Head Island to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Hilton Head Island with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Hilton Head Island to Caribbean

Get recent, data-driven insights about flights from Hilton Head Island to Caribbean including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Hilton Head Island to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $254). Flying from Hilton Head Island to Caribbean in March is currently the most expensive (average of $363). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated February 20, 2025.
United Airlines
7.4
Good
8,765 reviews

Food

6.7

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

United Airlines
7.4
Good
8,765 reviews
United Airlines
7.4
Good
8,765 reviews

Food

6.7

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,765 reviews

Food

6.7

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Hilton Head Island to Caribbean?

    Hilton Head Island (HHH), located 3.3 mi from the city center, is the airport you fly out of when you book flights from Hilton Head Island to Caribbean.

  • What are the most popular routes from Hilton Head Island to Caribbean?

    While some choose either Hilton Head Island - Montego Bay Sangster Intl or Hilton Head Island - Puerto Plata La Union, Hilton Head Island - Georgetown Exuma Intl is the most popular route from Hilton Head Island to Caribbean.

  • Can I find deals for flights from Hilton Head Island to Caribbean that include hotel bookings?

    Yes. In addition to deals on Hilton Head Island to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hilton Head Island to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Caribbean.

  • Can I find deals for business class flights from Hilton Head Island to Caribbean?

    Yes. Cheapflights offers flight deals from Hilton Head Island to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Hilton Head Island to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $254). Flying from Hilton Head Island to Caribbean in March is currently the most expensive (average of $363). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Hilton Head Island to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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