Bluebird
Hilton Head Island, South Carolina

Private charter · MDW → HHH

Chicago to Hilton Head Island

766 miles. One price for the whole airplane.

Photo: Mx. Granger · CC0

Price your flight from Chicago to Hilton Head Island

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Hilton Head Island, door to door faster.

Trade about 16½ hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Hilton Head Airport in Hilton Head Island, 766 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.

Distance
766 mi
Flight
—
Driving
16½ hours
Passengers
Up to 1
MDWChicagoHHHHilton Head Island
MDW → HHH766 miles direct

Departing Chicago

Airports in Chicago

  • MDW

    Major airport

    Chicago Midway International Airport

    Chicago · KMDW

    From downtown
    9 mi
    Longest runway
    6,522 ft

  • ORD

    Major airport

    Chicago O'Hare International Airport

    Chicago · KORD

    From downtown
    16 mi
    Longest runway
    13,000 ft

  • PWK

    Commercial airport

    Chicago Executive Airport

    Chicago/Prospect Heights/Wheeling · KPWK

    From downtown
    21 mi
    Longest runway
    5,001 ft

  • GYY

    Commercial airport

    Gary/Chicago International Airport

    Gary · KGYY

    From downtown
    21 mi
    Longest runway
    8,859 ft

Arriving Hilton Head Island

Airports in Hilton Head Island

  • HHH

    Commercial airport

    Hilton Head Airport

    Hilton Head Island · KHXD

    From downtown
    5 mi
    Longest runway
    5,000 ft

  • SAV

    Major airport

    Savannah Hilton Head International Airport

    Savannah · KSAV

    From downtown
    26 mi
    Longest runway
    9,351 ft

When you land

Things to do in Hilton Head Island

Hilton Head Island is a barrier island on South Carolina’s southern coast that was largely rural until the 1950s, when the first planned resort communities, led by Sea Pines, were developed with an emphasis on preserving the natural landscape. Today it is one of the East Coast’s best-known golf and beach destinations, with miles of hard-packed sand beaches, more than two dozen golf courses, extensive bike paths and a strong Gullah heritage. Tourism, golf, real estate and second homes drive the economy, and many residents are retirees and seasonal homeowners.

  1. 01

    Harbour Town

    In Sea Pines, a circular marina surrounded by shops and restaurants is watched over by the red-and-white striped Harbour Town Lighthouse, which visitors can climb for island views.

  2. 02

    Harbour Town Golf Links

    Designed by Pete Dye with Jack Nicklaus, this course hosts the PGA Tour’s RBC Heritage each April, finishing beside Calibogue Sound and the lighthouse.

  3. 03

    Coligny Beach Park

    The island’s main public beach has wide sand, changing areas and shaded swings, with Coligny Plaza’s shops and restaurants just across the street.

  4. 04

    Coastal Discovery Museum

    On the historic Honey Horn property, the museum offers exhibits on Lowcountry nature and history, butterfly gardens, marsh boardwalks and guided tours.

  5. 05

    Sea Pines Forest Preserve

    Within Sea Pines, the preserve’s trails and boardwalks lead through wetlands, past lakes with alligators and wading birds and to an ancient Native American shell ring.

  6. 06

    Daufuskie Island

    Reachable only by boat, this neighboring island preserves Gullah history, with sandy roads, artist studios, historic churches and quiet beaches.

Explore Hilton Head Island charter

Questions

Chicago to Hilton Head Island flights

How long is a private flight from Chicago to Hilton Head Island?

About a short flight in a private jet, for 766 miles direct. Driving the same trip takes about 16½ hours.

Which airports do flights from Chicago to Hilton Head Island use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Hilton Head Airport (HHH) or Savannah Hilton Head International Airport (SAV). Pick whichever is closest to where you're starting and where you're headed.

How much does a private charter from Chicago to Hilton Head Island cost?

The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.

Can I book a round trip between Chicago and Hilton Head Island?

Yes. Choose round trip when you search, and pick your return date and time. Flights from Hilton Head Island back to Chicago are priced the same way.

Return flight

Hilton Head Island to Chicago

More flights from Chicago

More flights to Hilton Head Island

Explore Chicago private charter and Hilton Head Island private charter, airports and things to do. Arriving at Hilton Head Airport (HHH).

Chicago to Hilton Head Island, on your schedule

Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.

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