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$139+ Cheap flights from Hilton Head Island (HHH) to Maryland

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BWI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Maryland

Keep the following information in mind while searching for Hilton Head Island to Maryland flight deals. Data was last updated September 15, 2025.

Round-trip from

$286
(American Airlines)

One-way from

$139
(American Airlines)
From Hilton Head Island to Maryland
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One-way flight from Hilton Head Island to Maryland
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Find flight deals from Hilton Head Island to Maryland

Cheapest flights from Hilton Head Island to Maryland
Explore the most affordable flight options available from Hilton Head Island to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Delta deal was found by Cheapflights users on 9/12. 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 10/112:14 pmHHH - BWI
1 stop5h 03mDelta
Wed 10/810:18 amBWI - HHH
1 stop5h 12mDelta
Deal found 9/12$257
This American Airlines deal was found by Cheapflights users on 9/12. 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 11/206:40 pmHHH - BWI
1 stop3h 44mAmerican Airlines
Mon 11/2411:09 amBWI - HHH
1 stop3h 48mAmerican Airlines
Deal found 9/12$276
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 10/175:57 pmHHH - BWI
1 stop6h 36mAmerican Airlines
Mon 10/201:05 pmBWI - HHH
1 stop4h 22mAmerican Airlines
Deal found 9/14$286
This American Airlines deal was found by Cheapflights users on 9/12. 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 12/136:48 pmHHH - BWI
1 stop3h 24mAmerican Airlines
Tue 12/166:00 amBWI - HHH
1 stop6h 22mAmerican Airlines
Deal found 9/12$327
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.
Wed 10/85:21 pmHHH - BWI
1 stop3h 27mAmerican Airlines
Fri 10/106:28 amBWI - HHH
1 stop5h 04mAmerican Airlines
Deal found 9/15$382
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 10/2411:16 amHHH - DCA
Nonstop1h 43mAmerican Airlines
Sun 10/268:24 amDCA - HHH
Nonstop2h 22mAmerican Airlines
Deal found 9/15$399
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 9/3012:56 pmHHH - BWI
1 stop4h 45mAmerican Airlines
Sat 10/411:04 amBWI - HHH
1 stop5h 43mAmerican Airlines
Deal found 9/15$405
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.
Tue 10/1412:45 pmHHH - PHL
1 stop4h 27mAmerican Airlines
Tue 10/2810:35 amPHL - HHH
1 stop6h 16mAmerican Airlines
Deal found 9/14$429
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/35:20 pmHHH - PHL
1 stop5h 57mAmerican Airlines
Mon 10/610:24 amPHL - HHH
1 stop4h 08mAmerican Airlines
Deal found 9/13$437
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/111:04 amHHH - DCA
Nonstop1h 55mAmerican Airlines
Wed 10/88:24 amDCA - HHH
Nonstop2h 22mAmerican Airlines
Deal found 9/13$441
This American Airlines deal was found by Cheapflights users on 9/13. 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 9/1711:04 amHHH - PHL
1 stop6h 43mAmerican Airlines
Sat 9/209:36 amPHL - HHH
2 stops7h 11mAmerican Airlines
Deal found 9/13$442
This American Airlines deal was found by Cheapflights users on 9/13. 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 12/132:17 pmHHH - IAD
1 stop5h 14mAmerican Airlines
Mon 12/157:59 amIAD - HHH
1 stop4h 23mAmerican Airlines
Deal found 9/13$459

Cheapflights Fare Finder

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

Fly from

Hilton Head Island

Fly to

Maryland

Route

Depart

Return

Price

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Wed 10/1

12:14 pm-5:17 pm

1 stop5h 03m

Baltimore/Washington

Wed 10/8

10:18 am-3:30 pm

1 stop5h 12m

$257

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Thu 11/20

6:40 pm-10:24 pm

1 stop3h 44m

Baltimore/Washington

Mon 11/24

11:09 am-2:57 pm

1 stop3h 48m

$276

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Fri 10/17

5:57 pm-12:33 am

1 stop6h 36m

Baltimore/Washington

Mon 10/20

1:05 pm-5:27 pm

1 stop4h 22m

$286

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Sat 12/13

6:48 pm-10:12 pm

1 stop3h 24m

Baltimore/Washington

Tue 12/16

6:00 am-12:22 pm

1 stop6h 22m

$327

Hilton Head IslandWashington, D.C.

HHH - DCA

HHHDCA

Hilton Head Island

Fri 10/24

11:16 am-12:59 pm

Nonstop1h 43m

Washington, D.C. Reagan-National

Sun 10/26

8:24 am-10:46 am

Nonstop2h 22m

$399

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Tue 9/30

12:56 pm-5:41 pm

1 stop4h 45m

Baltimore/Washington

Sat 10/4

11:04 am-4:47 pm

1 stop5h 43m

$405

Hilton Head IslandPhiladelphia

HHH - PHL

HHHPHL

Hilton Head Island

Tue 10/14

12:45 pm-5:12 pm

1 stop4h 27m

Philadelphia

Tue 10/28

7:00 am-4:51 pm

2 stops9h 51m

$434

Hilton Head IslandPhiladelphia

HHH - PHL

HHHPHL

Hilton Head Island

Mon 9/29

12:14 pm-5:20 pm

1 stop5h 06m

Philadelphia

Fri 10/3

10:30 am-3:25 pm

1 stop4h 55m

$437

Hilton Head IslandPhiladelphia

HHH - PHL

HHHPHL

Hilton Head Island

Fri 10/3

5:20 pm-11:17 pm

1 stop5h 57m

Philadelphia

Mon 10/6

10:24 am-2:32 pm

1 stop4h 08m

$437

Hilton Head IslandWashington, D.C.

HHH - DCA

HHHDCA

Hilton Head Island

Wed 10/1

11:04 am-12:59 pm

Nonstop1h 55m

Washington, D.C. Reagan-National

Wed 10/8

8:24 am-10:46 am

Nonstop2h 22m

$441

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 49 results
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Best time to book a flight from Hilton Head Island to Maryland

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

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

Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Maryland (average of $241). Flying from Hilton Head Island to Maryland in March is currently the most expensive (average of $290). 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 Maryland. 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 from for flights from Hilton Head Island to Maryland?

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

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

    Delta, American Airlines, and United Airlines can get you from Hilton Head Island to Maryland in just under 3h 44m. Your travel time can differ by up to 1h 19m. The distance between Hilton Head Island and Maryland is about 530 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $139 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 $217 and $383, respectively.

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

    The most popular route from Hilton Head Island to Maryland is Hilton Head Island - Washington, D.C. Dulles Intl. You may also consider Hilton Head Island - Philadelphia or Hilton Head Island - Baltimore/Washington.

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

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

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

    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 Maryland.

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

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

    Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Maryland (average of $241). Flying from Hilton Head Island to Maryland in March is currently the most expensive (average of $290). 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

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