Private Jets From Hilton Head Island to Chesapeake
Nonstop in about 1 hour and 33 minutes on the Cirrus Vision Jet.
The Better Way to Fly Private to Chesapeake
Fly private between Hilton Head Airport (HHH) and Chesapeake Regional Airport (CPK) aboard Flyte's Cirrus Vision Jet fleet. Featuring a whole-aircraft fare confirmed before you pay, on-demand availability, and advanced safety features.
Cirrus Vision Jet
The most advanced personal jet in the sky.
More Destinations
Hundreds of routes across the Southeast and beyond.
Garmin Autoland
The plane can detect an emergency and land itself.
CAPS Parachute
The only personal jet with a whole-aircraft parachute.
Private Cabin
The entire plane is yours. Four adults plus a child.
On Demand
Fly on your schedule. Any day, any time.
HHH to CPK by the Numbers
Hilton Head Airport to Chesapeake Regional Airport, nonstop on the Vision Jet.
- Flight time
- 1h 33m
- Nonstop on the Cirrus Vision Jet
- Distance
- 389 mi
- 338 nautical miles as the jet flies
- Driving
- 7h
- 463 miles by road, without stops
- Time saved
- 5h 53m
- Each way, versus driving
The Onboard Experience
Everything you need for a smoother trip between Hilton Head Island and Chesapeake.
Wi-Fi onboard
Stay connected when you need to work or relax en route, with reliable cabin Wi-Fi on available Flyte flights.
Complimentary food and beverages
Curated snacks, drinks, and light bites are included so you land refreshed.
Built-in advanced safety features
Every Flyte Vision Jet includes autoland and a whole-aircraft parachute as part of the aircraft design.
White-glove support
Our team helps coordinate any custom details so your trip stays smooth from first call to the ramp.
Things to Do in Chesapeake and Hilton Head Island
A few ways to spend your time at both ends of the flight.
Great Dismal Swamp National Wildlife Refuge
Kayak or hike through one of the East Coast most unique wetland ecosystems.
Visit Virginia Beach
Short drive to the oceanfront boardwalk, surfing, and seafood.
Norfolk Waterside District
Dining, entertainment, and harbor views in nearby downtown Norfolk.
Visit Coligny Beach Park
Enjoy the sun, sand, and surf at this popular beach with amenities like showers, restrooms, and nearby shops.
Explore Harbour Town
Discover the iconic red-and-white striped lighthouse, boutique shops, and waterfront dining in this charming area.
Play Golf at Harbour Town Golf Links
Tee off at one of the most famous golf courses in the country, known for hosting the RBC Heritage tournament.
Bike the Island
Rent a bike and explore over 60 miles of scenic trails that wind through the island's natural beauty.
Kayak or Paddleboard
Experience the island's waterways and wildlife by renting a kayak or paddleboard for a guided or solo adventure.
Visit the Coastal Discovery Museum
Learn about the island's history, culture, and natural environment through interactive exhibits and nature trails.
Dine at Hudson's Seafood House on the Docks
Enjoy fresh seafood with stunning views of the water at this local favorite restaurant.
Take a Dolphin Watching Tour
Join a boat tour to see playful dolphins in their natural habitat around the island.
Relax at a Spa
Indulge in a rejuvenating spa treatment at one of the island's luxurious spas.
Other Airports Near Chesapeake
More Flyte network airports around Chesapeake Regional Airport (CPK).
Norfolk International Airport
Norfolk, VA
Newport News Williamsburg International Airport
Newport News, VA
Richmond International Airport
Richmond, VA
Pitt-Greenville Airport
Greenville, NC
Hanover County Regional
Ashland, VA
Rocky Mount Wilson Regional Airport
Rocky Mount, NC
FAQs
Everything you need to know about flying Hilton Head Island to Chesapeake with Flyte.
Ready to Fly to Chesapeake?
Book your next private flight from Hilton Head Island (HHH) to Chesapeake (CPK). Pick your date and passengers and see your whole-aircraft fare before you pay.