Rome2Rio

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

Find Transport to Winston-Salem

See all options

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 52m
    $132–628

  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
    $98–206

  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
    $172–291

  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
    $144–461

  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 43m
    $134–751

  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
    $161–323

Chicago to Winston-Salem by bus

Calendar2Weekly Buses
Duration17h 58mAverage Duration
Ticket$172Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Winston-Salem.ExpandLaunch map view
  • Distance: 629.9 mi
  • Duration: 4h 52m

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.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers