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How to get fromChicago to Southern Pinesby plane, train, bus, taxi, train (Amtrak), or car

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There are 7 ways to get from Chicago to Southern Pines by plane, train, bus, taxi, train (Amtrak), 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 Chicago Midway International Airport to Raleigh-Durham International Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Raleigh-Durham International Airport (RDU)plane plane MDW - RDU
    2. Take the train from Cary to Southern Pines Stationtrain train
    7h 14m
    $178–351

  2. Drive 768.4 mi

    cheapest
    1. Drive from Chicago to Southern Pinescar car 768.4 mi
    14h 36m
    $141–203

  3. Bus, taxi

    1. Take the bus from Chicago Union Station to Toledobus bus
    2. Take the bus from Toledo Bus Stop to Winston Salem(Trans Center)bus bus
    3. Take the bus from Winston-Salem to Sanfordbus bus
    4. Take the taxi from Sanford to Southern Pinestaxi taxi
    22h 8m
    $266–409

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Southern Pines Stationtrain train Floridian
    25h 46m
    $370–750

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Raleigh-Durham International Airport (RDU)plane plane ORD - RDU
    2. Take the train from Cary to Southern Pines Stationtrain train
    7h 38m
    $198–801

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

    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 Carytrain train
    3. Take the train from Cary to Southern Pines Stationtrain train
    8h 39m
    $174–730

  7. Fly Chicago O'Hare International Airport to Charlotte Douglas International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Charlotte Douglas International Airport (CLT)plane plane ORD - CLT
    2. Take the train from Charlotte Amtrak Station to Carytrain train
    3. Take the train from Cary to Southern Pines Stationtrain train
    11h 9m
    $196–571

Chicago to Southern Pines by train (Amtrak)

Calendar7Weekly Trains
Duration25h 46mAverage Duration
Ticket$370Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Southern Pines.ExpandLaunch map view
  • Distance: 715.5 mi
  • Duration: 7h 14m

What companies run services between Chicago, IL, USA and Southern Pines, NC, USA?

Amtrak operates a train from Chicago Union Station to Southern Pines Station once daily. Tickets cost $370–750 and the journey takes 25h 46m.

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