$114 Cheap Flights from Hilton Head Island (HHH) to Boston (BOS)

View $114 flight on Tue, Jan 27, 2026Opens in a new window

Popular airlines from Hilton Head Island Airport (HHH) to Logan International Airport (BOS)

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Cheap Flights from Hilton Head Island to Boston (HHH-BOS)

Prices were available within the past 7 days and start at $114 for one-way flights and $217 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Dec 13 - Sun, Dec 14
HHH
Hilton Head Island
BOS
Boston
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Hilton Head Island to Boston, returning Sun, Dec 14, priced at $217 found 3 days ago
American Airlines
Thu, Dec 11 - Mon, Dec 15
HHH
Hilton Head Island
BOS
Boston
$227 Roundtrip, found 13 hours ago
$227
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Thu, Dec 11 from Hilton Head Island to Boston, returning Mon, Dec 15, priced at $227 found 13 hours ago
American Airlines
Mon, Dec 8 - Tue, Dec 9
HHH
Hilton Head Island
BOS
Boston
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Dec 8 from Hilton Head Island to Boston, returning Tue, Dec 9, priced at $237 found 5 days ago
American Airlines
Sun, Dec 7 - Sat, Dec 13
HHH
Hilton Head Island
BOS
Boston
$241 Roundtrip, found 5 days ago
$241
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Dec 7 from Hilton Head Island to Boston, returning Sat, Dec 13, priced at $241 found 5 days ago
American Airlines
Sat, Jan 17 - Sun, Jan 18
HHH
Hilton Head Island
BOS
Boston
$247 Roundtrip, found 5 days ago
$247
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Jan 17 from Hilton Head Island to Boston, returning Sun, Jan 18, priced at $247 found 5 days ago
American Airlines
Thu, Nov 13 - Thu, Nov 20
HHH
Hilton Head Island
BOS
Boston
$248 Roundtrip, found 2 days ago
$248
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Nov 13 from Hilton Head Island to Boston, returning Thu, Nov 20, priced at $248 found 2 days ago
American Airlines
Sat, Dec 13 - Sun, Dec 14
HHH
Hilton Head Island
BOS
Boston
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Hilton Head Island to Boston, returning Sun, Dec 14, priced at $257 found 3 days ago
American Airlines
Thu, Nov 13 - Thu, Nov 20
HHH
Hilton Head Island
BOS
Boston
$258 Roundtrip, found 2 days ago
$258
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Nov 13 from Hilton Head Island to Boston, returning Thu, Nov 20, priced at $258 found 2 days ago
American Airlines
Thu, Dec 11 - Mon, Dec 15
HHH
Hilton Head Island
BOS
Boston
$262 Roundtrip, found 13 hours ago
$262
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Thu, Dec 11 from Hilton Head Island to Boston, returning Mon, Dec 15, priced at $262 found 13 hours ago
American Airlines
Mon, Nov 24 - Fri, Nov 28
HHH
Hilton Head Island
BOS
Boston
$266 Roundtrip, found 3 days ago
$266
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Nov 24 from Hilton Head Island to Boston, returning Fri, Nov 28, priced at $266 found 3 days ago

Find the cheapest month to fly from Hilton Head Island (HHH) to Boston (BOS)

May is typically the cheapest month to fly

From $236 - $552 per traveler.

Frequently asked questions

How much does a flight from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS) cost?
Grab a cheap one-way flight from $114 or cheap return flight from $217 from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS)?
December is the most affordable month to fly from HHH to BOS. Avoiding peak travel times is often the key to finding better fares.
Which airlines fly direct from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS)?
Although Hilton Head Island, SC (HHH) has no direct flights to Logan Intl. Airport (BOS), other airports have nonstop routes. Leaving from Charleston Intl. Airport (CHS) will get you to Boston without any layovers.
What is the cheapest airline that flies from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS)?
To find the cheapest airline that'll fly you from HHH to BOS, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS)?
Direct flights from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from HHH to BOS?
Typically you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can vary depending on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS)?
To avoid potential delays on the Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS) route, fly before 3 PM. Later flights are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS) last-minute?
Last-minute bookings from HHH to BOS are usually more expensive. To lock in the cheapest rates, start looking for flights ahead of time. That said, if you can play around with your travel dates, it's possible to land a cheap ticket right before you leave.
Is it cheaper to book a HHH to BOS flight and hotel package?
Compared with arranging flights and hotels separately, booking a HHH to BOS flight and hotel package with Expedia could lead to significant savings. Better yet, having everything in one easy place takes the hassle out of planning your trip. Just pick your flights and choose from our extensive range of stays, then tailor your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from Hilton Head Island Airport (HHH) to Logan Intl. Airport (BOS)?
In most cases, you're able to cancel or reschedule your HHH to BOS flight. However, additional charges may apply, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you want further information, visit our Customer Service portal.

Travel information

Origin airport
Hilton Head Island
Destination airport
Logan Intl.
Airlines serving
American Airlines
Roundtrip price
$216
Distance
878 mi

Book with confidence

Hilton Head Island to Boston Flights

The cheapest times to fly from Hilton Head Island to Boston

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Hilton Head Island to Boston are during the month of December. You can find some of the cheapest flights from Hilton Head Island to Boston with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Hilton Head Island to Boston

Sunday is one of the best days to book for cheap flights from Hilton Head Island to Boston: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Hilton Head Island to Boston

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Hilton Head Island to Boston in 2025. You can also book with separate airlines for your outbound and return journeys, from $114 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Hilton Head Island to Boston flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Hilton Head Island to Boston airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Hilton Head Island to Boston Flights

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*Available to One Key members.