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Hilton Head Island

$205+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — HHH
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/319:12 amIAD - HHH
1 stop5h 04mAmerican Airlines
Sun 1/46:13 pmHHH - IAD
1 stop5h 51mAmerican Airlines
Deal found 12/17$494
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Mon 12/226:46 amDCA - HHH
1 stop3h 58mAmerican Airlines
Tue 12/302:46 pmHHH - DCA
1 stop5h 34mAmerican Airlines
Deal found 12/17$525
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/311:55 pmBWI - HHH
1 stop3h 48mAmerican Airlines
Sun 1/46:13 pmHHH - BWI
1 stop3h 52mAmerican Airlines
Deal found 12/17$549
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:35 amIAD - HHH
1 stop4h 09mAmerican Airlines
Sun 12/2811:14 amHHH - IAD
1 stop4h 45mAmerican Airlines
Deal found 12/16$549
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/266:46 amDCA - HHH
1 stop3h 58mAmerican Airlines
Mon 12/296:13 pmHHH - DCA
1 stop4h 02mAmerican Airlines
Deal found 12/17$562
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/266:35 amIAD - HHH
1 stop4h 09mAmerican Airlines
Sun 12/2811:14 amHHH - IAD
1 stop4h 45mAmerican Airlines
Deal found 12/17$562
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/266:42 amBWI - HHH
1 stop4h 02mAmerican Airlines
Tue 12/302:46 pmHHH - BWI
1 stop4h 39mAmerican Airlines
Deal found 12/17$567
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/266:46 amDCA - HHH
1 stop3h 58mAmerican Airlines
Sun 12/2811:14 amHHH - DCA
1 stop6h 20mAmerican Airlines
Deal found 12/17$572
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/266:42 amBWI - HHH
1 stop4h 02mAmerican Airlines
Mon 12/296:13 pmHHH - BWI
1 stop3h 52mAmerican Airlines
Deal found 12/17$623
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/178:00 amPHL - HHH
1 stop6h 57mAmerican Airlines
Wed 12/242:46 pmHHH - PHL
1 stop4h 48mAmerican Airlines
Deal found 12/16$630
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Mon 12/2910:35 amPHL - HHH
1 stop3h 41mAmerican Airlines
Fri 1/26:13 pmHHH - PHL
1 stop3h 38mAmerican Airlines
Deal found 12/17$655
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/191:57 pmBWI - HHH
1 stop3h 46mAmerican Airlines
Mon 12/226:13 pmHHH - BWI
1 stop3h 52mAmerican Airlines
Deal found 12/16$667

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$285
(American Airlines)

One-way from

$205
(American Airlines)

Popular in

April

Cheapest in

July

Average price

$399
Provider with most accurate pricing for Washington, D.C. (WAS)-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Hilton Head Island flights.
Search Deals
From Maryland to Hilton Head Island
Search Deals
One-way flight from Maryland to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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 2/3

9:17 am-2:59 pm

1 stop5h 42m

Hilton Head Island

Fri 2/6

3:29 pm-9:18 pm

1 stop5h 49m

$285

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Thu 1/15

11:13 am-2:59 pm

1 stop3h 46m

Hilton Head Island

Fri 1/16

3:29 pm-9:18 pm

1 stop5h 49m

$325

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Mon 5/4

6:47 am-10:14 am

1 stop3h 27m

Hilton Head Island

Sat 5/9

6:07 pm-12:25 am

1 stop6h 18m

$337

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Sat 4/18

5:04 am-10:14 am

1 stop5h 10m

Hilton Head Island

Wed 4/22

6:07 pm-12:25 am

1 stop6h 18m

$337

Washington, D.C.Hilton Head Island

DCA - HHH

DCAHHH

Washington, D.C. Reagan-National

Sat 2/14

1:44 pm-3:48 pm

Nonstop2h 04m

Hilton Head Island

Tue 2/17

4:15 pm-6:06 pm

Nonstop1h 51m

$359

Washington, D.C.Hilton Head Island

DCA - HHH

DCAHHH

Washington, D.C. Reagan-National

Fri 3/13

1:44 pm-3:41 pm

Nonstop1h 57m

Hilton Head Island

Wed 3/18

4:11 pm-5:59 pm

Nonstop1h 48m

$379

Washington, D.C.Hilton Head Island

DCA - HHH

DCAHHH

Washington, D.C. Reagan-National

Wed 1/14

6:59 am-12:20 pm

1 stop5h 21m

Hilton Head Island

Wed 1/21

12:51 pm-7:36 pm

1 stop6h 45m

$379

Washington, D.C.Hilton Head Island

DCA - HHH

DCAHHH

Washington, D.C. Reagan-National

Wed 2/18

1:40 pm-3:45 pm

Nonstop2h 05m

Hilton Head Island

Sun 2/22

4:08 pm-5:59 pm

Nonstop1h 51m

$379

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Sat 5/2

10:00 am-3:18 pm

1 stop5h 18m

Hilton Head Island

Wed 5/6

12:00 pm-5:06 pm

1 stop5h 06m

$388

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Sat 5/2

10:00 am-3:18 pm

1 stop5h 18m

Hilton Head Island

Tue 5/5

12:00 pm-5:06 pm

1 stop5h 06m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 52 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, June is the cheapest month in which you can book a flight from Maryland to Hilton Head Island (average of $84). Flying from Maryland to Hilton Head Island in November is currently the most expensive (average of $224). 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 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.

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

    American Airlines and Delta can get you from Maryland to Hilton Head Island in just under 5h 18m. Your travel time can differ by up to 24m. There are 530 mi between Maryland and Hilton Head Island. This flight may include one or multiple stops.

  • 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 Philadelphia - Hilton Head Island, Washington, D.C. Reagan-National - Hilton Head Island or Washington, D.C. Dulles Intl - 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, June is the cheapest month in which you can book a flight from Maryland to Hilton Head Island (average of $84). Flying from Maryland to Hilton Head Island in November is currently the most expensive (average of $224). 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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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$358FlexibilityNo cancel feeOn-time71%

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