Cheap Southwest Airlines flights Boston (BOS) to Hilton Head Island (HHH)

Landing cheap one-way Southwest Airlines flights from BOS to HHH on Expedia is simple — just filter by “Price (lowest to highest).” Or check out our affordable round-trip fares for your next getaway.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Look for one-way or return flights to Hilton Head Island in January or December. You could find a cheap fare with Southwest Airlines during these off-peak times.

Begin your search one to three months ahead of your departure date to get cheaper fares on Southwest Airlines flights from Logan Intl. Airport (BOS) to Hilton Head Island Airport (HHH). You can save 25% by booking your domestic flight 34 to 86 days in advance compared to last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it’s 6% cheaper on average than a Monday, the most expensive day to book.* Time it well, and you can enjoy significant savings on domestic trips.*Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

To figure out if there’s a direct journey from BOS to HHH with Southwest Airlines or another carrier, use our “Nonstop” filter when searching for tickets.

To find the earliest departures from BOS to HHH with Southwest Airlines, filter your search by “Morning” and “Early Morning.” Choosing an early flight usually means you’re less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Hilton Head Island Airport (HHH) is the main Hilton Head Island hub for Southwest Airlines flights from Logan Intl. Airport (BOS).

Changes are usually free within 24 hours of making your booking, but your airline may add a charge after that time. For further information about altering your flights, head to your “Trips,” select your flight and click on “Manage Booking.” If you’d like the freedom to adjust your plans without additional costs, check the “Changes included” and “No cancel fee” filters when organizing your next trip.