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Hilton Head Island

$148+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — HHH
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$276
(American Airlines)

One-way from

$148
(American Airlines)

Popular in

October

Cheapest in

February

Average price

$389
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. 7% potential increase in price ($34 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 September 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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 11/110:45 amBWI - HHH
1 stop3h 47mAmerican Airlines
Thu 11/66:40 pmHHH - BWI
1 stop3h 44mAmerican Airlines
Deal found 9/15$277
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/52:46 pmBWI - HHH
1 stop3h 51mAmerican Airlines
Mon 11/107:07 pmHHH - BWI
1 stop4h 28mAmerican Airlines
Deal found 9/14$286
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/308:13 amPHL - HHH
1 stop4h 04mAmerican Airlines
Sat 10/45:19 pmHHH - PHL
1 stop5h 58mAmerican Airlines
Deal found 9/15$357
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/225:04 amBWI - HHH
1 stop6h 04mAmerican Airlines
Wed 11/266:40 pmHHH - BWI
1 stop3h 44mAmerican Airlines
Deal found 9/15$359
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/188:24 amDCA - HHH
Nonstop2h 22mAmerican Airlines
Tue 10/2111:16 amHHH - DCA
Nonstop1h 43mAmerican Airlines
Deal found 9/14$359
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/310:00 amBWI - HHH
1 stop6h 47mAmerican Airlines
Fri 10/105:57 pmHHH - BWI
1 stop6h 36mAmerican Airlines
Deal found 9/14$372
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/3011:11 amBWI - HHH
1 stop5h 40mAmerican Airlines
Mon 11/37:07 pmHHH - BWI
1 stop4h 28mAmerican Airlines
Deal found 9/14$373
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/410:00 amBWI - HHH
1 stop6h 47mAmerican Airlines
Tue 10/712:45 pmHHH - BWI
1 stop6h 44mAmerican Airlines
Deal found 9/15$379
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/221:44 pmDCA - HHH
1 stop4h 25mAmerican Airlines
Wed 11/262:51 pmHHH - DCA
1 stop5h 08mAmerican Airlines
Deal found 9/14$379
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/57:55 amIAD - HHH
1 stop4h 34mAmerican Airlines
Sat 11/86:48 pmHHH - IAD
1 stop5h 11mAmerican Airlines
Deal found 9/14$379
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/311:04 amBWI - HHH
1 stop5h 43mAmerican Airlines
Tue 10/75:21 pmHHH - BWI
1 stop3h 27mAmerican Airlines
Deal found 9/15$384
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/88:20 amDCA - HHH
1 stop5h 59mAmerican Airlines
Mon 11/1011:28 amHHH - DCA
Nonstop1h 46mAmerican Airlines
Deal found 9/14$389

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 September 15, 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

Sat 11/1

10:45 am-2:32 pm

1 stop3h 47m

Hilton Head Island

Thu 11/6

6:40 pm-10:24 pm

1 stop3h 44m

$277

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Sat 11/22

5:04 am-11:08 am

1 stop6h 04m

Hilton Head Island

Wed 11/26

6:40 pm-10:24 pm

1 stop3h 44m

$359

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Fri 10/3

10:00 am-4:47 pm

1 stop6h 47m

Hilton Head Island

Fri 10/10

5:57 pm-12:33 am

1 stop6h 36m

$372

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Sat 10/4

10:00 am-4:47 pm

1 stop6h 47m

Hilton Head Island

Tue 10/7

12:45 pm-7:29 pm

1 stop6h 44m

$379

Washington, D.C.Hilton Head Island

IAD - HHH

IADHHH

Washington, D.C. Dulles Intl

Wed 11/5

7:55 am-12:29 pm

1 stop4h 34m

Hilton Head Island

Tue 11/11

7:07 pm-11:07 pm

1 stop4h 00m

$379

Washington, D.C.Hilton Head Island

DCA - HHH

DCAHHH

Washington, D.C. Reagan-National

Thu 10/30

8:24 am-10:46 am

Nonstop2h 22m

Hilton Head Island

Mon 11/3

11:28 am-1:14 pm

Nonstop1h 46m

$399

Washington, D.C.Hilton Head Island

DCA - HHH

DCAHHH

Washington, D.C. Reagan-National

Sat 11/8

7:00 am-11:16 am

1 stop4h 16m

Hilton Head Island

Mon 11/10

3:27 pm-8:15 pm

1 stop4h 48m

$399

Washington, D.C.Hilton Head Island

IAD - HHH

IADHHH

Washington, D.C. Dulles Intl

Sat 11/1

6:34 am-11:32 am

1 stop4h 58m

Hilton Head Island

Thu 11/6

6:40 pm-11:59 pm

1 stop5h 19m

$399

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Tue 9/30

10:05 am-4:47 pm

1 stop6h 42m

Hilton Head Island

Sat 10/4

5:19 pm-8:52 pm

1 stop3h 33m

$405

BaltimoreHilton Head Island

BWI - HHH

BWIHHH

Baltimore/Washington

Mon 9/29

10:00 am-4:47 pm

1 stop6h 47m

Hilton Head Island

Fri 10/3

12:56 pm-7:20 pm

1 stop6h 24m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 59 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.

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 United Airlines can get you from Maryland to Hilton Head Island in just under 3h 47m. Your travel time can differ by up to 1h 18m. There are 530 mi between Maryland and Hilton Head Island. This flight may include one or multiple stops.

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

    $148 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 $153 and $278, 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, Washington, D.C. Reagan-National - Hilton Head Island or Baltimore/Washington - 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$363FlexibilityNo cancel feeOn-time71%

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