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How to get fromChicago to South Bostonby plane, car, bus (Greyhound), train, taxi, or bus

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There are 9 ways to get from Chicago to South Boston by plane, car, bus (Greyhound), train, taxi, or bus

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 Midway International Airport to Raleigh-Durham International Airport, drive

    best
    1. Fly from Chicago Midway International Airport (MDW) to Raleigh-Durham International Airport (RDU)plane plane MDW - RDU
    2. Drive from Raleigh-Durham-Airport-RDU to South Bostoncar car
    4h 54m
    $164–323

  2. Drive 720.7 mi

    cheapest
    1. Drive from Chicago to South Bostoncar car 720.7 mi
    14h 32m
    $132–190

  3. Bus

    1. Take the bus from Chicago Bus Station to Washington Union Stationbus bus Greyhound US0164
    2. Take the bus from Washington Union Station to South Boston Pilot Travel Centerbus bus Capitol Connector
    22h 35m
    $154–264

  4. Train, taxi

    1. Take the train from Chicago Union Station to Charlottesvilletrain train
    2. Take the train from Charlottesville to Danville Stationtrain train
    3. Take the taxi from Danville Station to South Bostontaxi taxi
    24h 50m
    $371–707

  5. Fly Chicago O'Hare International Airport to Raleigh-Durham International Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Raleigh-Durham International Airport (RDU)plane plane ORD - RDU
    2. Drive from Raleigh-Durham-Airport-RDU to South Bostoncar car
    5h 18m
    $184–773

  6. Fly Chicago O'Hare International Airport to Lynchburg Regional Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Lynchburg Regional Airport (LYH)plane plane ORD - LYH
    2. Take the taxi from Lynchburg-Airport-LYH to South Bostontaxi taxi
    5h 11m
    $192–525

  7. Fly Chicago O'Hare International Airport to Piedmont Triad International Airport, train, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Piedmont Triad International Airport (GSO)plane plane ORD - GSO
    2. Take the train from Greensboro to Danville Stationtrain train
    3. Take the taxi from Danville Station to South Bostontaxi taxi
    6h 40m
    $226–770

  8. Fly Chicago Midway International Airport to Richmond International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Richmond International Airport (RIC)plane plane MDW - RIC
    2. Take the bus from GRTC Bus Stop at Main St Station to South Boston Pilot Travel Centerbus bus
    8h 15m
    $138–599

  9. Train, bus

    1. Take the train from Chicago Union Station to Richmond Staples Mill Road Amtrak Stationtrain train Floridian
    2. Take the bus from GRTC Bus Stop at Main St Station to South Boston Pilot Travel Centerbus bus Capitol Connector
    25h 22m
    $317–625

Chicago Midway International Airport (MDW) to Raleigh-Durham International Airport (RDU) flights

Calendar21Weekly Planes
Duration1h 55mAverage Duration
Ticket$100Cheapest Price
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Questions & Answers

Map of how to get from Chicago to South Boston.ExpandLaunch map view
  • Distance: 707.8 mi
  • Duration: 4h 54m

What companies run services between Chicago, IL, USA and South Boston, VA, USA?

You can take a bus from Chicago Bus Station to South Boston via Washington Union Station and South Boston Pilot Travel Center in around 22h 35m.

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