Bluebird
Winston-Salem, North Carolina

Private charter · MDW → INT

Chicago to Winston-Salem

562 miles. One price for the whole airplane.

Photo: Indy beetle · CC0

Price your flight from Chicago to Winston-Salem

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Winston-Salem, door to door faster.

Trade about 12 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Smith Reynolds Airport in Winston-Salem, 562 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
562 mi
Flight
—
Driving
12 hours
Passengers
Up to 1
MDWChicagoINTWinston-Salem
MDW → INT562 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 Winston-Salem

Airports in Winston-Salem

  • INT

    Commercial airport

    Smith Reynolds Airport

    Winston Salem · KINT

    From downtown
    3 mi
    Longest runway
    6,655 ft

  • GSO

    Major airport

    Piedmont Triad International Airport

    Greensboro · KGSO

    From downtown
    18 mi
    Longest runway
    10,001 ft

  • KEXX

    Regional airport

    Davidson County Executive Airport

    Lexington

    From downtown
    22 mi
    Longest runway
    5,004 ft

  • KMWK

    Regional airport

    Mount Airy Surry County Airport

    Mount Airy

    From downtown
    30 mi
    Longest runway
    5,500 ft

When you land

Things to do in Winston-Salem

Winston-Salem took its name from the merger of two towns: Salem, founded by Moravian settlers in 1766, and Winston, which grew rich on tobacco and textiles as the home of R.J. Reynolds and Hanes. Today Wake Forest University and its academic medical center are the largest economic engines, and the Innovation Quarter has turned former tobacco buildings downtown into labs, offices and apartments. The University of North Carolina School of the Arts adds a strong cultural life, and Krispy Kreme was founded here.

  1. 01

    Old Salem Museums and Gardens

    This restored Moravian town features historic buildings, costumed interpreters, heritage gardens and Winkler Bakery, still known for its Moravian sugar cake and thin, spiced cookies.

  2. 02

    Reynolda House Museum of American Art

    R.J. Reynolds’s 1917 country estate now displays an important collection of American art, with formal gardens and Reynolda Village’s shops and restaurants next door.

  3. 03

    Pilot Mountain State Park

    North of the city, the distinctive rocky knob of Pilot Mountain rises above the Piedmont, with hiking trails, overlooks and climbing routes.

  4. 04

    Hanging Rock State Park

    Waterfalls, rock outcrops and a mountain lake make this park in the Sauratown Mountains a favorite for hiking, swimming and paddling.

  5. 05

    Yadkin Valley Wine Country

    North Carolina’s first federally designated wine region lies just west of the city, with dozens of wineries and tasting rooms set among rolling vineyards.

  6. 06

    Downtown Arts District

    Trade Street and the surrounding blocks are lined with galleries, studios and restaurants, and the district hosts popular gallery hops and street festivals.

Explore Winston-Salem charter

Questions

Chicago to Winston-Salem flights

How long is a private flight from Chicago to Winston-Salem?

About a short flight in a private jet, for 562 miles direct. Driving the same trip takes about 12 hours.

Which airports do flights from Chicago to Winston-Salem use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Smith Reynolds Airport (INT), Piedmont Triad International Airport (GSO), or Davidson County Executive Airport (KEXX). Pick whichever is closest to where you're starting and where you're headed.

How much does a private charter from Chicago to Winston-Salem 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 Winston-Salem?

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

Return flight

Winston-Salem to Chicago

More flights from Chicago

More flights to Winston-Salem

Explore Chicago private charter and Winston-Salem private charter, airports and things to do. Arriving at Smith Reynolds Airport (INT).

Chicago to Winston-Salem, 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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