HHH - BOS

$180 Find Cheap Flights from Hilton Head Island to Boston - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$341
Typical prices: $308-$560
American Airlines
Wed 12/5Sat 12/8
HHH - BOS • 1 stop
Cheapest one-way
$180
Typical prices: $159-$338
American Airlines
Fri 11/23
HHH - BOS • 1 stop
When to travel
January
Cheapest • 35% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Charlotte Douglas (CLT)
Cheapest • Avg $418 (round-trip)
Washington, D.C. Reagan-National (DCA)
Shortest trip • 5h 11m (one-way)
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Cheap Flights from Hilton Head Island to Boston (HHH-BOS)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hilton Head Island to Boston

Sat, Dec 5 - Tue, Dec 8
American Airlines Logo
1:13 pm - 8:20 pmHHH  Hilton Head Island-BOS Boston Logan Intl
7h 07m1 stop Charlotte Douglas
American Airlines Logo
7:11 am - 12:03 pmBOS  Boston Logan Intl-HHH Hilton Head Island
4h 52m1 stop Charlotte Douglas
$341American Airlines
Fri, Dec 4 - Mon, Dec 7
American Airlines Logo
5:54 pm - 11:02 pmHHH  Hilton Head Island-BOS Boston Logan Intl
5h 08m1 stop Charlotte Douglas
American Airlines Logo
7:11 am - 12:03 pmBOS  Boston Logan Intl-HHH Hilton Head Island
4h 52m1 stop Charlotte Douglas
$359American Airlines
Fri, Dec 4 - Mon, Dec 7
American Airlines Logo
5:54 pm - 11:02 pmHHH  Hilton Head Island-BOS Boston Logan Intl
5h 08m1 stop Charlotte Douglas
American Airlines Logo
7:11 am - 12:03 pmBOS  Boston Logan Intl-HHH Hilton Head Island
4h 52m1 stop Charlotte Douglas
$359American Airlines
Thu, Nov 12 - Mon, Nov 16
American Airlines Logo
5:54 pm - 11:07 pmHHH  Hilton Head Island-BOS Boston Logan Intl
5h 13m1 stop Charlotte Douglas
American Airlines Logo
7:15 am - 11:53 amBOS  Boston Logan Intl-HHH Hilton Head Island
4h 38m1 stop Charlotte Douglas
$389American Airlines
Wed, Nov 11 - Sun, Nov 15
American Airlines Logo
4:17 pm - 9:50 pmHHH  Hilton Head Island-BOS Boston Logan Intl
5h 33m1 stop Charlotte Douglas
American Airlines Logo
10:12 am - 5:10 pmBOS  Boston Logan Intl-HHH Hilton Head Island
6h 58m1 stop Charlotte Douglas
$389American Airlines
Tue, Nov 10 - Sat, Nov 14
American Airlines Logo
4:17 pm - 9:50 pmHHH  Hilton Head Island-BOS Boston Logan Intl
5h 33m1 stop Charlotte Douglas
American Airlines Logo
9:26 am - 3:47 pmBOS  Boston Logan Intl-HHH Hilton Head Island
6h 21m1 stop Charlotte Douglas
$389American Airlines
Mon, Nov 23 - Mon, Nov 30
American Airlines Logo
5:47 pm - 11:07 pmHHH  Hilton Head Island-BOS Boston Logan Intl
5h 20m1 stop Charlotte Douglas
American Airlines Logo
5:40 am - 10:36 amBOS  Boston Logan Intl-HHH Hilton Head Island
4h 56m1 stop Charlotte Douglas
$404American Airlines
Sat, Dec 5 - Tue, Dec 8
American Airlines Logo
1:13 pm - 10:59 pmHHH  Hilton Head Island-BOS Boston Logan Intl
9h 46m2 stops Charlotte Douglas Philadelphia
American Airlines Logo
11:13 am - 3:53 pmBOS  Boston Logan Intl-HHH Hilton Head Island
4h 40m1 stop Charlotte Douglas
$419American Airlines
Wed, Apr 28 - Sat, May 1
United Airlines Logo
3:05 pm - 11:16 pmHHH  Hilton Head Island-BOS Boston Logan Intl
8h 11m1 stop Chicago O'Hare Intl
United Airlines Logo
7:10 am - 2:16 pmBOS  Boston Logan Intl-HHH Hilton Head Island
7h 06m1 stop Chicago O'Hare Intl
$459United Airlines
Wed, Apr 28 - Sat, May 1
United Airlines Logo
3:05 pm - 11:16 pmHHH  Hilton Head Island-BOS Boston Logan Intl
8h 11m1 stop Chicago O'Hare Intl
United Airlines Logo
6:00 am - 2:16 pmBOS  Boston Logan Intl-HHH Hilton Head Island
8h 16m2 stops Newark Chicago O'Hare Intl
$464United Airlines
Booking Insights

Price, demand and travel trends for Hilton Head Island to Boston flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Hilton Head Island to Boston?

Round-trip flights from Hilton Head Island to Boston typically range from $308 to $560. The lowest price found in the past 5 days was $341, on American Airlines.

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Key details for Hilton Head Island to Boston flights

Low season

October

Cheapest flight

$180
Beat the crowds with an average 81% drop in travelers.
The most popular month to fly with an average 21% increase in travelers.
One-way flight from Hilton Head Island to Boston

When to book flights from Hilton Head Island to Boston

Are your dates flexible? Find out the best times to travel from Hilton Head Island to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Hilton Head Island to Boston flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Hilton Head Island to Boston?

    Only Economy Class is available on flights from Hilton Head Island to Boston.

  • How long is a flight from Hilton Head Island to Boston?

    There are currently no nonstop flights available from Hilton Head Island to Boston. Flights with 1 layover take between 5h and 5h 17m in total, depending on the connection.

  • Do I need a passport to fly from Hilton Head Island to Boston?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Hilton Head Island to Boston flight?

    Round-trip flights from Hilton Head Island to Boston range from $308 to $560, with an average of $428 over the past 12 months. Anything below $308 counts as a good deal.

  • How much can I save by taking a layover when flying from Hilton Head Island to Boston?

    On this route, nonstop and layover fares are close on average, with nonstop at $423 round-trip and layover options via Charlotte Douglas (CLT) at $418.

  • Have flight prices from Hilton Head Island to Boston changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $341 to $922. That means the highest observed fare was about 3x higher than the lowest one.

  • How are flight prices from Hilton Head Island to Boston looking right now?

    One-way fares from Hilton Head Island to Boston are currently higher than usual. Average one-way flight prices are about $402, which is 88% above the typical average for this route.

  • What car rental options are available at Boston Logan Intl Airport (BOS)?

    Boston Logan Intl Airport (BOS) hosts 5 major car rental companies, with daily rates averaging $77 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Budget
    • Thrifty
    • Sixt

  • Which airports can I use when flying from Hilton Head Island to Boston?

    Flights from Hilton Head Island to Boston usually depart from Hilton Head Island (HHH) and arrive at Boston Logan Intl (BOS).

  • Which airports do connecting flights from Hilton Head Island to Boston pass through?

    One-stop flights from Hilton Head Island to Boston most commonly connect through:

    • Charlotte Douglas (CLT) - 88% of one-stop connections
    • Washington, D.C. Reagan-National (DCA) - 6% of one-stop connections
    • Newark (EWR) - 6% of one-stop connections

  • Can I save money by using flexible dates for flights from Hilton Head Island to Boston?

    Yes. Flexible dates can save you up to 26% on flights from Hilton Head Island to Boston. Wednesday is the cheapest departure day at $388 round-trip on average, while Friday is the most expensive at $519, a difference of $131.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Hilton Head Island to Boston?

    Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 5h, compared with 5h 11m via Washington, D.C. Reagan-National (DCA) and 5h 17m via Newark (EWR).

  • What popular places can I visit in Boston?

    Some of the most popular sights in Boston are TD Garden, Fenway Park and Boston Common. These are among the most viewed places in Boston on KAYAK.

Your guide to booking Hilton Head Island to Boston flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Friday. On this route, Wednesday flights average $388, about $131 less than Friday fares (25% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Hilton Head Island to Boston trip for January. Fares historically average $277 round-trip in that month - typically $311 less than the most expensive month, which is April (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Charlotte Douglas Airport (CLT) can be cheaper than flying direct. The cheapest layover option averages $418 round-trip on this route - about $5 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Boston Logan Intl Airport.

    • Hyatt Regency Boston Harbor
    • Hilton Garden Inn Boston Logan Airport
    • Hilton Boston Logan Airport

More options for your flight from Hilton Head Island to Boston

Complete your trip to Boston with a hotel stay or car rental

Car rentals in Boston
Hotels in Boston
Vacations in Boston