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$347+ Cheap flights from Hilton Head Island (HHH) to Costa Rica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJO
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Costa Rica

Cheapest flights from Hilton Head Island to Costa Rica
Explore the most affordable flight options available from Hilton Head Island to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 17, 2026.

This American Airlines deal was found by Cheapflights users on 3/12. 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.
Thu 5/215:21 pm
HHH
-
SJO
2 stops21h 47m
American Airlines
Thu 5/2811:59 pm
SJO
-
HHH
2 stops14h 33m
American Airlines
Deal found 3/12$644
This Delta deal was found by Cheapflights users on 3/15. 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.
Mon 8/34:00 pm
HHH
-
SJO
2 stops22h 00m
Delta
Tue 8/111:21 pm
SJO
-
HHH
2 stops20h 02m
Delta
Deal found 3/15$714
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 3/304:11 pm
HHH
-
SJO
2 stops20h 00m
United Airlines
Thu 4/91:25 pm
SJO
-
HHH
2 stops22h 51m
United Airlines
Deal found 3/15$731
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Wed 4/13:05 pm
HHH
-
SJO
2 stops45h 06m
United Airlines
Thu 4/91:25 pm
SJO
-
HHH
2 stops22h 51m
United Airlines
Deal found 3/15$753
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 3/303:00 pm
HHH
-
SJO
2 stops21h 11m
United Airlines
Tue 4/141:25 pm
SJO
-
HHH
2 stops22h 51m
United Airlines
Deal found 3/15$761
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 8/33:05 pm
HHH
-
SJO
2 stops21h 06m
United Airlines
Sun 8/912:30 am
SJO
-
HHH
2 stops35h 31m
United Airlines
Deal found 3/15$772
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 8/33:05 pm
HHH
-
SJO
2 stops21h 06m
United Airlines
Sun 8/97:55 am
SJO
-
HHH
2 stops28h 26m
United Airlines
Deal found 3/15$777
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Thu 7/303:05 pm
HHH
-
SJO
2 stops23h 16m
United Airlines
Wed 8/51:25 pm
SJO
-
HHH
2 stops22h 56m
United Airlines
Deal found 3/15$779
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Wed 4/13:05 pm
HHH
-
SJO
2 stops45h 06m
United Airlines
Fri 4/107:55 am
SJO
-
HHH
2 stops28h 21m
United Airlines
Deal found 3/15$783
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Thu 4/304:39 pm
HHH
-
LIR
2 stops21h 31m
United Airlines
Thu 5/73:27 pm
LIR
-
HHH
2 stops20h 44m
United Airlines
Deal found 3/16$824
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Sun 4/263:05 pm
HHH
-
LIR
2 stops23h 05m
United Airlines
Sun 5/33:27 pm
LIR
-
HHH
2 stops22h 14m
United Airlines
Deal found 3/12$1,101
This American Airlines deal was found by Cheapflights users on 3/12. 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 4/266:39 pm
HHH
-
LIR
1 stop18h 49m
American Airlines
Sun 5/312:27 pm
LIR
-
HHH
2 stops20h 05m
American Airlines
Deal found 3/12$3,729

Find flight deals from Hilton Head Island to Costa Rica

Keep the following information in mind while searching for Hilton Head Island to Costa Rica flight deals. Data was last updated March 17, 2026.

Round-trip from

$644
(American Airlines)

One-way from

$347
(American Airlines)
From Hilton Head Island to Costa Rica
Search Deals
One-way flight from Hilton Head Island to Costa Rica
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Costa Rica 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 March 17, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Thu 5/21

5:21 pm-1:08 pm

2 stops21h 47m

San José Juan Santamaria Intl

Thu 5/28

11:59 pm-4:32 pm

2 stops14h 33m

$644

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Mon 8/3

3:05 pm-10:11 am

2 stops21h 06m

San José Juan Santamaria Intl

Wed 8/5

1:25 pm-2:21 pm

2 stops22h 56m

$793

Hilton Head IslandLiberia

HHH - LIR

HHHLIR

Hilton Head Island

Thu 4/30

4:39 pm-12:10 pm

2 stops21h 31m

Liberia

Thu 5/7

3:27 pm-2:11 pm

2 stops20h 44m

$824

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Tue 8/4

4:00 pm-12:00 pm

2 stops22h 00m

San José Juan Santamaria Intl

Thu 8/6

1:25 pm-3:18 pm

1 stop23h 53m

$1,017

Hilton Head IslandLiberia

HHH - LIR

HHHLIR

Hilton Head Island

Sun 4/26

3:05 pm-12:10 pm

2 stops23h 05m

Liberia

Sun 5/3

3:27 pm-3:41 pm

2 stops22h 14m

$1,101

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Mon 8/3

12:00 pm-12:00 pm

1 stop26h 00m

San José Juan Santamaria Intl

Mon 8/10

1:21 pm-3:20 pm

1 stop23h 59m

$1,158

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Wed 7/29

12:00 pm-12:00 pm

1 stop26h 00m

San José Juan Santamaria Intl

Wed 8/5

1:25 pm-3:18 pm

1 stop23h 53m

$1,295

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Mon 8/3

12:00 pm-12:00 pm

1 stop26h 00m

San José Juan Santamaria Intl

Fri 8/7

1:25 pm-3:18 pm

1 stop23h 53m

$1,531

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Sun 8/2

12:00 pm-12:00 pm

1 stop26h 00m

San José Juan Santamaria Intl

Wed 8/5

1:25 pm-3:18 pm

1 stop23h 53m

$1,783

Hilton Head IslandLiberia

HHH - LIR

HHHLIR

Hilton Head Island

Sun 4/26

6:39 pm-11:28 am

1 stop18h 49m

Liberia

Sun 5/3

12:27 pm-10:32 am

2 stops20h 05m

$3,729

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

Showing 1-10 of 14 resultsSorted by cheapest first
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Best time to book a flight from Hilton Head Island to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica 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.

Cheapflights Insights

Everything you need to know about your flight from Hilton Head Island to Costa Rica

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

Currently, December is the cheapest month in which you can book a flight from Hilton Head Island to Costa Rica (average of $90). Flying from Hilton Head Island to Costa Rica in May is currently the most expensive (average of $445). 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.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Costa Rica. 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 Costa Rica?

    Located just 3.3 mi from the city center, Hilton Head Island (HHH) is the airport most travelers will use when flying to Costa Rica from Hilton Head Island.

  • How long is the flight from Hilton Head Island to Costa Rica?

    American Airlines and United Airlines can get you from Hilton Head Island to Costa Rica in just under 21h 11m. Your travel time can differ by up to 36m. Airlines will cover a distance of 1551 mi. This flight may include one or multiple stops.

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

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

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

    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 Costa Rica.

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

    Yes. Cheapflights offers flight deals from Hilton Head Island to Costa Rica 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 Costa Rica?

    Currently, December is the cheapest month in which you can book a flight from Hilton Head Island to Costa Rica (average of $90). Flying from Hilton Head Island to Costa Rica in May is currently the most expensive (average of $445). 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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