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$295+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJO
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
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 enero 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/28. 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.
mar. 6/165:54 pm
HHH
-
SJO
2 stops21h 13m
American Airlines
mar. 6/233:12 pm
SJO
-
HHH
2 stops21h 06m
American Airlines
Deal found 1/28$531
This American Airlines deal was found by Cheapflights users on 1/27. 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.
sáb. 2/286:20 pm
HHH
-
SJO
2 stops17h 04m
American Airlines
mar. 3/102:20 pm
SJO
-
HHH
2 stops22h 02m
American Airlines
Deal found 1/27$630
This American Airlines deal was found by Cheapflights users on 1/27. 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.
sáb. 2/286:20 pm
HHH
-
SJO
2 stops17h 04m
American Airlines
jue. 3/1210:25 am
SJO
-
HHH
2 stops22h 08m
American Airlines
Deal found 1/27$641
This American Airlines deal was found by Cheapflights users on 1/27. 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.
sáb. 2/286:20 pm
HHH
-
SJO
1 stop19h 26m
American Airlines
mié. 3/1111:35 pm
SJO
-
HHH
2 stops32h 58m
American Airlines
Deal found 1/27$643
This American Airlines deal was found by Cheapflights users on 1/27. 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.
sáb. 2/286:20 pm
HHH
-
SJO
2 stops17h 04m
American Airlines
lun. 3/92:59 pm
SJO
-
HHH
2 stops18h 54m
American Airlines
Deal found 1/27$648
This American Airlines deal was found by Cheapflights users on 1/27. 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.
sáb. 2/286:20 pm
HHH
-
SJO
2 stops17h 04m
American Airlines
dom. 3/82:25 pm
SJO
-
HHH
2 stops18h 08m
American Airlines
Deal found 1/27$653
This American Airlines deal was found by Cheapflights users on 1/27. 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.
sáb. 2/286:20 pm
HHH
-
SJO
1 stop19h 26m
American Airlines
sáb. 3/73:59 pm
SJO
-
HHH
2 stops23h 45m
American Airlines
Deal found 1/27$655

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 enero 29, 2026.

Round-trip from

$531
(American Airlines)

One-way from

$295
(United 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 enero 29, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Costa Rica that are best for you.

Fly from

Hilton Head Island

Fly to

Costa Rica

Route

Depart

Return

Price

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

mar. 6/16

5:54 pm-1:07 pm

2 stops21h 13m

San José Juan Santamaria Intl

mar. 6/23

3:12 pm-2:18 pm

2 stops21h 06m

$531

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

mié. 3/4

12:23 pm-8:33 pm

2 stops9h 10m

San José Juan Santamaria Intl

mar. 3/10

2:59 pm-3:41 pm

2 stops22h 42m

$630

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

lun. 3/2

6:20 pm-8:33 pm

2 stops27h 13m

San José Juan Santamaria Intl

mar. 3/10

2:20 pm-2:22 pm

2 stops22h 02m

$630

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

mar. 3/3

5:19 pm-12:31 pm

2 stops20h 12m

San José Juan Santamaria Intl

mar. 3/10

2:20 pm-2:22 pm

2 stops22h 02m

$630

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

sáb. 2/28

6:20 pm-12:46 pm

1 stop19h 26m

San José Juan Santamaria Intl

mar. 3/10

1:50 pm-10:33 am

1 stop18h 43m

$640

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

lun. 3/2

2:58 pm-12:31 pm

2 stops22h 33m

San José Juan Santamaria Intl

jue. 3/12

2:59 pm-10:33 am

2 stops17h 34m

$641

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

mar. 3/3

5:19 pm-12:31 pm

2 stops20h 12m

San José Juan Santamaria Intl

jue. 3/12

10:25 am-10:33 am

2 stops22h 08m

$641

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

mié. 3/4

12:23 pm-8:33 pm

2 stops9h 10m

San José Juan Santamaria Intl

jue. 3/12

2:59 pm-10:33 am

2 stops17h 34m

$641

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

mar. 3/3

12:23 pm-8:33 pm

2 stops9h 10m

San José Juan Santamaria Intl

mié. 3/11

6:00 am-2:22 pm

2 stops30h 22m

$645

Hilton Head IslandLiberia

HHH - LIR

HHHLIR

Hilton Head Island

lun. 7/13

3:00 pm-10:00 am

2 stops21h 00m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 16 results
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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 can get you from Hilton Head Island to Costa Rica in just under 21h 13m. Your travel time can differ by up to . Airlines will cover a distance of 1551 mi.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Hilton Head Island to Costa Rica

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