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Hilton Head Island

$100+ Cheap flights from Maryland to Hilton Head Island (HHH)

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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — HHH
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Maryland to Hilton Head Island

Keep the following information in mind while searching for Maryland to Hilton Head Island flight deals. Data was last updated July 31, 2025.

Round-trip from

$257
(American Airlines)

One-way from

$100
(American Airlines)

Popular in

October

Cheapest in

February

Average price

$375
From Maryland to Hilton Head Island
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One-way flight from Maryland to Hilton Head Island
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Highest demand for flights based on searches. 4% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Maryland to Hilton Head Island

Cheapest flights from Maryland to Hilton Head Island
Explore the most affordable flight options available from Maryland to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 9/26:00 amBWI - HHH
1 stop5h 59mAmerican Airlines
Sat 9/63:26 pmHHH - BWI
1 stop5h 26mAmerican Airlines
Deal found 7/30$257
This Delta deal was found by Cheapflights users on 7/31. 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 10/76:00 amBWI - HHH
2 stops9h 30mDelta
Thu 10/912:17 pmHHH - BWI
1 stop6h 23mDelta
Deal found 7/31$262
This Delta deal was found by Cheapflights users on 7/30. 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 9/277:00 amDCA - HHH
1 stop4h 30mDelta
Wed 10/14:05 pmHHH - DCA
1 stop15h 13mDelta
Deal found 7/30$348
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/135:00 pmDCA - HHH
Nonstop1h 54mAmerican Airlines
Sat 9/2011:17 amHHH - DCA
Nonstop1h 55mAmerican Airlines
Deal found 7/30$359
This Delta deal was found by Cheapflights users on 7/30. 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 10/110:07 amIAD - HHH
1 stop5h 18mDelta
Sat 10/412:14 pmHHH - IAD
1 stop6h 25mDelta
Deal found 7/30$379
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/236:31 amPHL - HHH
1 stop8h 40mAmerican Airlines
Sat 8/303:41 pmHHH - PHL
1 stop30h 06mAmerican Airlines
Deal found 7/29$390
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/2611:18 amIAD - HHH
1 stop5h 29mAmerican Airlines
Tue 9/303:26 pmHHH - IAD
1 stop3h 25mAmerican Airlines
Deal found 7/30$399
This Delta deal was found by Cheapflights users on 7/31. 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 9/102:35 pmPHL - HHH
1 stop24h 50mDelta
Tue 9/1612:14 pmHHH - PHL
1 stop25h 21mDelta
Deal found 7/31$405
This United Airlines deal was found by Cheapflights users on 7/31. 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 8/247:00 amDCA - HHH
1 stop4h 21mUnited Airlines
Mon 9/812:06 pmHHH - DCA
1 stop4h 16mUnited Airlines
Deal found 7/31$464
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 8/3012:50 pmIAD - HHH
2 stops22h 31mUnited Airlines
Wed 9/312:06 pmHHH - IAD
1 stop4h 17mUnited Airlines
Deal found 7/30$483

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maryland 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 July 31, 2025.
Use the filters below to find and compare flights from Maryland to Hilton Head Island that are best for you.

Fly from

Maryland

Fly to

Hilton Head Island

Route

Depart

Return

Price

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Tue 9/2

6:00 am-11:59 am

1 stop5h 59m

Hilton Head Island

Sat 9/6

3:26 pm-8:52 pm

1 stop5h 26m

$257

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Tue 10/7

6:00 am-3:30 pm

2 stops9h 30m

Hilton Head Island

Thu 10/9

12:17 pm-6:40 pm

1 stop6h 23m

$262

Washington, D.C.Hilton Head Island

DCA - HHH

DCAHHH

Washington, D.C. Reagan-National

Sat 9/27

7:00 am-11:30 am

1 stop4h 30m

Hilton Head Island

Wed 10/1

4:05 pm-7:18 am

1 stop15h 13m

$348

Washington, D.C.Hilton Head Island

DCA - HHH

DCAHHH

Washington, D.C. Reagan-National

Sat 9/13

5:00 pm-6:54 pm

Nonstop1h 54m

Hilton Head Island

Sat 9/20

11:17 am-1:12 pm

Nonstop1h 55m

$359

Washington, D.C.Hilton Head Island

IAD - HHH

IADHHH

Washington, D.C. Dulles Intl

Wed 10/1

10:07 am-3:25 pm

1 stop5h 18m

Hilton Head Island

Sat 10/4

12:14 pm-6:39 pm

1 stop6h 25m

$379

PhiladelphiaHilton Head Island

PHL - HHH

PHLHHH

Philadelphia

Sat 8/23

6:31 am-3:11 pm

1 stop8h 40m

Hilton Head Island

Sat 8/30

3:41 pm-9:47 pm

1 stop30h 06m

$390

Washington, D.C.Hilton Head Island

IAD - HHH

IADHHH

Washington, D.C. Dulles Intl

Fri 9/26

11:18 am-4:47 pm

1 stop5h 29m

Hilton Head Island

Tue 9/30

3:26 pm-6:51 pm

1 stop3h 25m

$399

PhiladelphiaHilton Head Island

PHL - HHH

PHLHHH

Philadelphia

Wed 9/10

2:35 pm-3:25 pm

1 stop24h 50m

Hilton Head Island

Tue 9/16

12:14 pm-1:35 pm

1 stop25h 21m

$405

Washington, D.C.Hilton Head Island

DCA - HHH

DCAHHH

Washington, D.C. Reagan-National

Sun 8/24

7:00 am-11:21 am

1 stop4h 21m

Hilton Head Island

Mon 9/8

12:06 pm-4:22 pm

1 stop4h 16m

$464

Washington, D.C.Hilton Head Island

IAD - HHH

IADHHH

Washington, D.C. Dulles Intl

Sat 8/30

12:50 pm-11:21 am

2 stops22h 31m

Hilton Head Island

Wed 9/3

12:06 pm-4:23 pm

1 stop4h 17m

$483

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 21 results
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Best time to book a flight from Maryland to Hilton Head Island

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

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

Currently, January is the cheapest month in which you can book a flight from Maryland to Hilton Head Island (average of $275). Flying from Maryland to Hilton Head Island in March is currently the most expensive (average of $480). 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.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. 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 Hilton Head Island. Reviews last updated July 31, 2025.
Read through reviews of airlines operating flights from Maryland to Hilton Head Island, such as Delta, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Maryland 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.

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

    For a flight from Maryland to Hilton Head Island, you will be flying into Hilton Head. Hilton Head Island (HHH) is just 3.3 mi from the center of the city.

  • What are the cheapest airlines to fly from Maryland to Hilton Head Island one-way?

    $100 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $114 and $285, respectively.

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

    When deciding which route to take from Maryland to Hilton Head Island consider Washington, D.C. Dulles Intl - Hilton Head Island, Baltimore/Washington - Hilton Head Island or Philadelphia - Hilton Head Island as they are the most popular.

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

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

  • How can I find direct flights from Maryland 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 Maryland to Hilton Head Island.

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

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

    Currently, January is the cheapest month in which you can book a flight from Maryland to Hilton Head Island (average of $275). Flying from Maryland to Hilton Head Island in March is currently the most expensive (average of $480). 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
Bluffton

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Alternative routes for Maryland to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Maryland to Hilton Head Island

Discover the top airline that operate flights from Maryland to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$359FlexibilityNo cancel feeOn-time71%

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