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Hilton Head Island

$642+ Cheap flights from Oakland, CA to Hilton Head Island (OAK - HHH)

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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — HHH
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Oakland to Hilton Head Island

Cheapest flights from Oakland to Hilton Head Island
Explore the most affordable flight options available from Oakland to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Tue 5/512:08 pm
HHH
-
OAK
2 stops14h 46m
Delta
Deal found 1/27$642
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/212:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Tue 5/512:08 pm
HHH
-
OAK
2 stops14h 46m
Delta
Deal found 1/27$680
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Mon 5/412:08 pm
HHH
-
OAK
2 stops31h 16m
Delta
Deal found 1/27$709
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/212:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Fri 5/812:00 pm
HHH
-
OAK
2 stops14h 49m
Delta
Deal found 1/27$720
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Wed 5/612:08 pm
HHH
-
OAK
2 stops14h 46m
Delta
Deal found 1/27$745
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Thu 4/3012:08 pm
HHH
-
OAK
2 stops14h 46m
Delta
Deal found 1/27$785
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Tue 5/512:08 pm
HHH
-
OAK
2 stops14h 46m
Delta
Deal found 1/27$815
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Fri 5/112:08 pm
HHH
-
OAK
2 stops26h 45m
Delta
Deal found 1/27$850
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Fri 5/812:00 pm
HHH
-
OAK
2 stops14h 49m
Delta
Deal found 1/27$855
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Mon 5/412:08 pm
HHH
-
OAK
2 stops31h 16m
Delta
Deal found 1/27$863
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:04 pm
OAK
-
HHH
2 stops43h 16m
Delta
Tue 5/512:08 pm
HHH
-
OAK
2 stops14h 46m
Delta
Deal found 1/27$894
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:34 pm
OAK
-
HHH
2 stops23h 46m
Delta
Wed 5/612:08 pm
HHH
-
OAK
2 stops14h 46m
Delta
Deal found 1/27$899

Find flight deals from Oakland to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Hilton Head Island (HHH). 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.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$642
(Delta)

Popular in

November

Cheapest in

September

Average price

$560
Provider with most accurate pricing for San Francisco-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Hilton Head Island flights.
Search Deals
From Oakland to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($226 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($50 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Hilton Head Island 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 Oakland to Hilton Head Island that are best for you.

Fly from

Oakland

Fly to

Hilton Head Island

Route

Depart

Return

Price

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Tue 4/28

12:34 pm-3:20 pm

2 stops23h 46m

Hilton Head Island

Tue 5/5

12:08 pm-11:54 pm

2 stops14h 46m

$642

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Tue 4/28

12:34 pm-3:20 pm

2 stops23h 46m

Hilton Head Island

Mon 5/4

12:08 pm-4:24 pm

2 stops31h 16m

$709

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Sat 5/2

12:34 pm-3:20 pm

2 stops23h 46m

Hilton Head Island

Mon 5/4

12:08 pm-4:24 pm

2 stops31h 16m

$709

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Sat 5/2

12:34 pm-3:20 pm

2 stops23h 46m

Hilton Head Island

Fri 5/8

12:00 pm-11:49 pm

2 stops14h 49m

$720

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Tue 4/28

12:34 pm-3:20 pm

2 stops23h 46m

Hilton Head Island

Wed 5/6

12:08 pm-11:54 pm

2 stops14h 46m

$745

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Sat 5/2

12:34 pm-3:20 pm

2 stops23h 46m

Hilton Head Island

Wed 5/6

12:08 pm-11:54 pm

2 stops14h 46m

$745

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Tue 4/28

12:34 pm-3:20 pm

2 stops23h 46m

Hilton Head Island

Thu 4/30

12:08 pm-11:54 pm

2 stops14h 46m

$785

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Fri 5/1

5:04 pm-3:20 pm

2 stops19h 16m

Hilton Head Island

Tue 5/5

12:08 pm-11:54 pm

2 stops14h 46m

$815

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Tue 4/28

12:34 pm-3:20 pm

2 stops23h 46m

Hilton Head Island

Fri 5/1

12:08 pm-11:53 am

2 stops26h 45m

$850

OaklandHilton Head Island

OAK - HHH

OAKHHH

Oakland

Fri 5/1

12:34 pm-3:20 pm

2 stops23h 46m

Hilton Head Island

Fri 5/8

12:00 pm-11:49 pm

2 stops14h 49m

$855

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 12 results
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Best time to book a flight from Oakland to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Oakland 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 Oakland to Hilton Head Island

What is the cheapest month to book a flight from Oakland, California to Hilton Head Island?

Currently, May is the cheapest month in which you can book a flight from Oakland, California to Hilton Head Island (average of $148). Flying from Oakland, California to Hilton Head Island in March is currently the most expensive (average of $276). 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 Oakland to Hilton Head Island. 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 Oakland, California to Hilton Head Island?

    Airlines like Delta fly from Oakland, California to Hilton Head Island in about 23h 46m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 2360 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Hilton Head Island 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 Oakland, California to Hilton Head Island?

    Currently, May is the cheapest month in which you can book a flight from Oakland, California to Hilton Head Island (average of $148). Flying from Oakland, California to Hilton Head Island in March is currently the most expensive (average of $276). 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 Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort

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