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

Find Transport to Winston-Salem

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There are 7 ways to get from Chicago to Winston-Salem by plane, bus, bus (Amtrak, Greyhound), car, train, or bus (Greyhound)

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 Chicago O'Hare International Airport to Piedmont Triad International Airport, line 1 bus

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Piedmont Triad International Airport (GSO)plane plane ORD - GSO
    2. Take the bus from Coble Transportation Center to Winston-Salem Transportation Centerbus bus
    4h 49m
    $132–678

  2. Bus via Columbus

    cheapest
    1. Take the bus from Chicago to Columbus - Mound Stbus bus Chicago / ...
    2. Take the bus from Columbus to Winston Salem(Trans Center)bus bus Greyhound US0140
    18h 10m
    $98–186

  3. Bus

    1. Take the bus from Chicago Union Station to Toledobus bus Amtrak Thruway Connecting Service
    2. Take the bus from Toledo Bus Stop to Winston Salem(Trans Center)bus bus Greyhound US0140
    17h 58m
    $148–233

  4. Drive  675.4 mi

    1. Drive from Chicago to Winston-Salemcar car 675.4 mi
    12h 44m
    $124–178

  5. Fly Chicago O'Hare International Airport to Charlotte Douglas International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Charlotte Douglas International Airport (CLT)plane plane ORD - CLT
    2. Take the bus from Charlotte Bus Station to Winston Salem(Trans Center)bus bus
    7h 2m
    $134–441

  6. Fly Chicago Midway International Airport to Charlotte Douglas International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Charlotte Douglas International Airport (CLT)plane plane MDW - CLT
    2. Take the bus from Charlotte Bus Station to Winston Salem(Trans Center)bus bus
    6h 38m
    $124–701

  7. Train, bus

    1. Take the train from Chicago Union Station to Toledotrain train Floridian / ...
    2. Take the bus from Toledo Bus Stop to Winston Salem(Trans Center)bus bus Greyhound US0140
    17h 59m
    $145–272

Chicago to Winston-Salem by bus

Calendar2Weekly Buses
Duration17h 58mAverage Duration
Ticket$148Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Winston-Salem.ExpandLaunch map view
  • Distance: 629.9 mi
  • Duration: 4h 49m

What companies run services between Chicago, IL, USA and Winston-Salem, NC, USA?

You can take a bus from Chicago Union Station to Winston Salem(Trans Center) via Toledo Bus Stop in around 17h 58m.

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