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How to get fromChicago to Pittsboroby plane, taxi, bus (Amtrak, Greyhound), train (Amtrak), or car

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There are 6 ways to get from Chicago to Pittsboro by plane, taxi, bus (Amtrak, Greyhound), 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, taxi

    best
    1. Fly from Chicago Midway International Airport (MDW) to Raleigh-Durham International Airport (RDU)plane plane MDW - RDU
    2. Take the taxi from Raleigh-Durham-Airport-RDU to Pittsborotaxi taxi
    4h 1m
    $238–415

  2. Drive 744.9 mi

    cheapest
    1. Drive from Chicago to Pittsborocar car 744.9 mi
    13h 59m
    $136–197

  3. Bus

    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(Trans Center) to Siler Citybus bus
    21h 44m
    $216–352

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Carytrain train Floridian
    24h 58m
    $409–793

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Raleigh-Durham International Airport (RDU)plane plane ORD - RDU
    2. Take the taxi from Raleigh-Durham-Airport-RDU to Pittsborotaxi taxi
    4h 25m
    $258–865

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Piedmont Triad International Airport (GSO)plane plane ORD - GSO
    2. Take the taxi from Piedmont Triad International Airport (GSO) to Pittsborotaxi taxi
    4h 53m
    $242–775

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 Pittsboro.ExpandLaunch map view
  • Distance: 672.5 mi
  • Duration: 4h 1m

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

You can take a bus from Chicago Union Station to Pittsboro via Toledo Bus Stop, Winston Salem(Trans Center), and Siler City in around 21h 44m. Alternatively, Amtrak operates a train from Chicago Union Station to Cary once daily. Tickets cost $340–750 and the journey takes 24h 26m.

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