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How to get fromChesapeake to Winston-Salemby plane, train, bus, bus (Greyhound), or car

Find Transport to Winston-Salem

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There are 5 ways to get from Chesapeake to Winston-Salem by plane, train, bus, bus (Greyhound), or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly to Piedmont Triad International Airport

    best
    1. Fly from Norfolk International Airport (ORF) to Piedmont Triad International Airport (GSO)plane plane ORF - GSO
    4h 41m
    $157–756

  2. Drive  250.4 mi

    cheapest
    1. Drive from Chesapeake to Winston-Salemcar car 250.4 mi
    5h 9m
    $46–66

  3. Train, bus

    1. Take the train from Norfolk to Petersburg Amtrak Stationtrain train
    2. Take the train from Petersburg Amtrak Station to Greensborotrain train
    3. Take the bus from Greensboro Bus Stop to Winston Salem(Trans Center)bus bus
    8h 59m
    $181–288

  4. Bus (Greyhound)

    1. Take the bus from Norfolk to Winston Salem(Trans Center)bus bus Greyhound US0654s
    9h 4m
    $47–82

  5. Fly to Charlotte Douglas International Airport, bus

    1. Fly from Norfolk International Airport (ORF) to Charlotte Douglas International Airport (CLT)plane plane ORF - CLT
    2. Take the bus from Charlotte Bus Station to Winston Salem(Trans Center)bus bus
    4h 47m
    $114–529

Chesapeake to Winston-Salem by train and bus

Calendar7Weekly Services
Duration8h 59mAverage Duration
Ticket$181Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chesapeake to Winston-Salem.ExpandLaunch map view
  • Distance: 245.5 mi
  • Duration: 4h 41m

What companies run services between Chesapeake, City of Chesapeake, VA, USA and Winston-Salem, NC, USA?

United Airlines, American Airlines, and Delta fly from Norfolk International Airport (ORF) to Piedmont Triad International Airport (GSO) hourly. Alternatively, Greyhound USA operates a bus from Norfolk to Winston Salem(Trans Center) once daily. Tickets cost $45–80 and the journey takes 7h 25m.

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