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$135+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BWI
Jan 6 — Jan 131
Tue 1/6
Tue 1/13
1 adult, Economy
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Cheap 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 December 7, 2025.

This American Airlines deal was found by Cheapflights users on 12/5. 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 12/242:46 pmHHH - BWI
1 stop3h 24mAmerican Airlines
Wed 12/311:55 pmBWI - HHH
1 stop3h 48mAmerican Airlines
Deal found 12/5$417
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/316:13 pmHHH - DCA
1 stop4h 02mAmerican Airlines
Tue 1/610:10 pmDCA - HHH
2 stops16h 49mAmerican Airlines
Deal found 12/6$418
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/3111:14 amHHH - BWI
1 stop5h 48mAmerican Airlines
Wed 1/711:13 amBWI - HHH
1 stop3h 46mAmerican Airlines
Deal found 12/6$419
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/216:13 pmHHH - BWI
1 stop3h 52mAmerican Airlines
Thu 12/256:42 amBWI - HHH
1 stop4h 02mAmerican Airlines
Deal found 12/6$421
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/3111:14 amHHH - BWI
1 stop5h 48mAmerican Airlines
Sun 1/45:06 amBWI - HHH
1 stop5h 38mAmerican Airlines
Deal found 12/6$438
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/3111:14 amHHH - IAD
1 stop4h 45mAmerican Airlines
Thu 1/19:12 amIAD - HHH
1 stop5h 04mAmerican Airlines
Deal found 12/6$439
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/3111:14 amHHH - DCA
1 stop6h 20mAmerican Airlines
Wed 1/710:10 amDCA - HHH
1 stop4h 49mAmerican Airlines
Deal found 12/6$439
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/3111:14 amHHH - DCA
1 stop6h 20mAmerican Airlines
Thu 1/16:30 amDCA - HHH
2 stops7h 46mAmerican Airlines
Deal found 12/6$444
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/3011:14 amHHH - DCA
1 stop6h 20mAmerican Airlines
Tue 1/610:10 pmDCA - HHH
2 stops14h 10mAmerican Airlines
Deal found 12/6$449
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/3011:14 amHHH - BWI
1 stop5h 48mAmerican Airlines
Thu 1/16:42 amBWI - HHH
1 stop4h 02mAmerican Airlines
Deal found 12/6$450
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/3011:14 amHHH - DCA
2 stops9h 58mAmerican Airlines
Wed 1/710:10 pmDCA - HHH
2 stops14h 10mAmerican Airlines
Deal found 12/6$454
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/3011:14 amHHH - BWI
1 stop5h 48mAmerican Airlines
Mon 1/51:55 pmBWI - HHH
1 stop3h 48mAmerican Airlines
Deal found 12/6$457

Find 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 December 7, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$234
(American Airlines)

One-way from

$135
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Washington, D.C. (WAS) flights.
Search Deals
From Hilton Head Island to Maryland
Search Deals
One-way flight from Hilton Head Island to Maryland
Search Deals

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 December 7, 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 IslandWashington, D.C.

HHH - DCA

HHHDCA

Hilton Head Island

Mon 1/5

11:14 am-5:34 pm

1 stop6h 20m

Washington, D.C. Reagan-National

Mon 1/5

9:10 pm-12:20 pm

2 stops15h 10m

$293

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Tue 5/26

6:24 pm-12:15 am

1 stop5h 51m

Baltimore/Washington

Sat 5/30

6:59 am-10:10 am

1 stop3h 11m

$377

Hilton Head IslandWashington, D.C.

HHH - DCA

HHHDCA

Hilton Head Island

Mon 1/5

6:13 pm-7:26 am

2 stops13h 13m

Washington, D.C. Reagan-National

Tue 1/6

10:10 pm-12:20 pm

2 stops14h 10m

$398

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Wed 12/24

2:46 pm-6:10 pm

1 stop3h 24m

Baltimore/Washington

Wed 12/31

1:55 pm-5:43 pm

1 stop3h 48m

$417

Hilton Head IslandWashington, D.C.

HHH - DCA

HHHDCA

Hilton Head Island

Wed 12/31

11:14 am-5:34 pm

1 stop6h 20m

Washington, D.C. Reagan-National

Wed 1/7

10:10 pm-12:20 pm

2 stops14h 10m

$418

Hilton Head IslandWashington, D.C.

HHH - DCA

HHHDCA

Hilton Head Island

Thu 1/1

6:13 pm-10:15 pm

1 stop4h 02m

Washington, D.C. Reagan-National

Tue 1/6

10:10 pm-12:20 pm

2 stops14h 10m

$418

Hilton Head IslandWashington, D.C.

HHH - DCA

HHHDCA

Hilton Head Island

Thu 1/1

6:13 pm-10:15 pm

1 stop4h 02m

Washington, D.C. Reagan-National

Mon 1/5

6:20 pm-12:20 pm

2 stops18h 00m

$418

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Thu 1/1

11:14 am-5:02 pm

1 stop5h 48m

Baltimore/Washington

Tue 1/6

6:00 am-12:20 pm

1 stop6h 20m

$419

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Thu 1/1

11:14 am-5:02 pm

1 stop5h 48m

Baltimore/Washington

Wed 1/7

11:13 am-2:59 pm

1 stop3h 46m

$419

Hilton Head IslandBaltimore

HHH - BWI

HHHBWI

Hilton Head Island

Wed 12/31

6:13 pm-10:05 pm

1 stop3h 52m

Baltimore/Washington

Tue 1/6

11:13 am-2:59 pm

1 stop3h 46m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 56 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 $100). Flying from Hilton Head Island to Maryland in February is currently the most expensive (average of $245). 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?

    American Airlines can get you from Hilton Head Island to Maryland in just under 6h 20m. Your travel time can differ by up to . The distance between Hilton Head Island and Maryland is about 502 mi.

  • 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 $100). Flying from Hilton Head Island to Maryland in February is currently the most expensive (average of $245). 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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