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How to get fromWinston-Salem to Chicagoby plane, bus, train, car, or bus (Greyhound, Amtrak)

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There are 9 ways to get from Winston-Salem to Chicago by plane, bus, train, car, or bus (Greyhound, Amtrak)

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 Piedmont Triad International Airport to Chicago O'Hare International Airport

    best
    1. Fly from Piedmont Triad International Airport (GSO) to Chicago O'Hare International Airport (ORD)plane plane GSO - ORD
    4h 45m
    $80–388

  2. Bus

    cheapest
    1. Take the bus from Winston Salem to Columbusbus bus Bsb 33
    2. Take the bus from Columbus to Chicagobus bus Bsb 21 / ...
    19h 5m
    $72–172

  3. Bus, train

    1. Take the bus from Winston Salem(Trans Center) to Greensboro Bus Stopbus bus
    2. Take the train from Greensboro to Raleigh Union Stationtrain train
    3. Take the train from Raleigh Union Station to Chicago Union Stationtrain train
    28h 50m
    $595–1,027

  4. Drive  688.2 mi

    1. Drive from Winston-Salem to Chicagocar car 688.2 mi
    12h 9m
    $126–182

  5. Bus to Charlotte Douglas International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Winston Salem(Trans Center) to Charlotte Bus Stationbus bus
    2. Fly from Charlotte Douglas International Airport (CLT) to Chicago Midway International Airport (MDW)plane plane CLT - MDW
    5h 40m
    $90–451

  6. Bus to Charlotte Douglas International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Winston Salem(Trans Center) to Charlotte Bus Stationbus bus
    2. Fly from Charlotte Douglas International Airport (CLT) to Chicago O'Hare International Airport (ORD)plane plane CLT - ORD
    6h 3m
    $75–351

  7. Bus to Raleigh-Durham International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Winston Salem(Trans Center) to Durhambus bus
    2. Fly from Raleigh-Durham International Airport (RDU) to Chicago Midway International Airport (MDW)plane plane RDU - MDW
    6h 54m
    $95–452

  8. Bus to Raleigh-Durham International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Winston Salem(Trans Center) to Durhambus bus
    2. Fly from Raleigh-Durham International Airport (RDU) to Chicago O'Hare International Airport (ORD)plane plane RDU - ORD
    7h 31m
    $75–352

  9. Bus via Toledo

    1. Take the bus from Winston Salem(Trans Center) to Charlotte Bus Stationbus bus
    2. Take the bus from Charlotte Bus Station to Toledo Bus Stopbus bus
    3. Take the bus from Toledo to Chicago Union Stationbus bus
    21h 22m

Winston-Salem to Chicago by bus

Calendar7Weekly Buses
Duration19h 5mAverage Duration
Ticket$72Cheapest Price
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Comparing Your Travel Options

Map of how to get from Winston-Salem to Chicago.ExpandLaunch map view
  • Distance: 630.3 mi
  • Duration: 4h 45m

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

American Airlines, United Airlines, and Delta fly from Piedmont Triad International Airport (GSO) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a bus from Baptist Hospital to Chicago via Winston Salem and Columbus in around 19h 5m.

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