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San José

$310+ Cheap flights from Hilton Head Island (HHH) to San José (SJO)

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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Hilton Head Island to San José

Cheapest flights from Hilton Head Island to San José
Explore the most affordable flight options available from Hilton Head Island to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 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.
Tue 6/165:54 pm
HHH
-
SJO
2 stops21h 13m
American Airlines
Tue 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.
Sat 2/286:20 pm
HHH
-
SJO
2 stops17h 04m
American Airlines
Tue 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.
Sat 2/286:20 pm
HHH
-
SJO
2 stops17h 04m
American Airlines
Thu 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.
Sat 2/286:20 pm
HHH
-
SJO
1 stop19h 26m
American Airlines
Wed 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.
Sat 2/286:20 pm
HHH
-
SJO
2 stops17h 04m
American Airlines
Mon 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.
Sat 2/286:20 pm
HHH
-
SJO
2 stops17h 04m
American Airlines
Sun 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.
Sat 2/286:20 pm
HHH
-
SJO
1 stop19h 26m
American Airlines
Sat 3/73:59 pm
SJO
-
HHH
2 stops23h 45m
American Airlines
Deal found 1/27$655

Find flight deals from Hilton Head Island to San José

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to San José (SJO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 29, 2026.

Round-trip from

$531
(American Airlines)

One-way from

$310
(American Airlines)
From Hilton Head Island to San José Juan Santamaria Intl
Search Deals
One-way flight from Hilton Head Island to San José Juan Santamaria Intl
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to San José 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 January 29, 2026.
Use the filters below to find and compare flights from Hilton Head Island to San José that are best for you.

Fly from

Hilton Head Island

Fly to

San José

Route

Depart

Return

Price

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Tue 6/16

5:54 pm-1:07 pm

2 stops21h 13m

San José Juan Santamaria Intl

Tue 6/23

3:12 pm-2:18 pm

2 stops21h 06m

$531

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Wed 3/4

12:23 pm-8:33 pm

2 stops9h 10m

San José Juan Santamaria Intl

Tue 3/10

2:59 pm-3:41 pm

2 stops22h 42m

$630

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Mon 3/2

6:20 pm-8:33 pm

2 stops27h 13m

San José Juan Santamaria Intl

Tue 3/10

2:20 pm-2:22 pm

2 stops22h 02m

$630

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Tue 3/3

5:19 pm-12:31 pm

2 stops20h 12m

San José Juan Santamaria Intl

Tue 3/10

2:20 pm-2:22 pm

2 stops22h 02m

$630

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Sat 2/28

6:20 pm-12:46 pm

1 stop19h 26m

San José Juan Santamaria Intl

Tue 3/10

1:50 pm-10:33 am

1 stop18h 43m

$640

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Mon 3/2

2:58 pm-12:31 pm

2 stops22h 33m

San José Juan Santamaria Intl

Thu 3/12

2:59 pm-10:33 am

2 stops17h 34m

$641

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Tue 3/3

5:19 pm-12:31 pm

2 stops20h 12m

San José Juan Santamaria Intl

Thu 3/12

10:25 am-10:33 am

2 stops22h 08m

$641

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Wed 3/4

12:23 pm-8:33 pm

2 stops9h 10m

San José Juan Santamaria Intl

Thu 3/12

2:59 pm-10:33 am

2 stops17h 34m

$641

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Tue 3/3

12:23 pm-8:33 pm

2 stops9h 10m

San José Juan Santamaria Intl

Wed 3/11

6:00 am-2:22 pm

2 stops30h 22m

$645

Hilton Head IslandSan José

HHH - SJO

HHHSJO

Hilton Head Island

Sat 7/11

5:54 pm-1:07 pm

2 stops21h 13m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 11 results
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Best time to book a flight from Hilton Head Island to San José

Have a flexible travel schedule? Discover the best time to fly to San José 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 San José

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

Currently, December is the cheapest month in which you can book a flight from Hilton Head Island to San José (average of $90). Flying from Hilton Head Island to San José in July is currently the most expensive (average of $456). 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 San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Hilton Head Island to San José?

    For as low as $531, American Airlines can have you in San José from Hilton Head Island in 21h 13m. Airlines will cover a distance of 1551 mi.

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

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

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

    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 San José.

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

    Yes. Cheapflights offers flight deals from Hilton Head Island to San José 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 San José?

    Currently, December is the cheapest month in which you can book a flight from Hilton Head Island to San José (average of $90). Flying from Hilton Head Island to San José in July is currently the most expensive (average of $456). 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

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Alajuela
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio

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