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How to get fromRoseburg to Chicagoby car, plane, train, bus, or taxi

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There are 5 ways to get from Roseburg to Chicago by car, plane, train, bus, or taxi

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Drive, fly to Chicago O'Hare International Airport

    best
    1. Drive from Roseburg to Eugene-Airport-EUGcar car
    2. Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)plane plane EUG - ORD
    6h 27m
    $116–475

  2. Drive, train (Amtrak)

    1. Drive from Roseburg to Eugenecar car
    2. Take the train from Eugene to Portlandtrain train
    3. Take the train from Portland to Chicago Union Stationtrain train
    2d 2h
    $753–1,604

  3. Drive 2,146.7 mi

    1. Drive from Roseburg to Chicagocar car 2,146.7 mi
    37h 10m
    $392–566

  4. Drive, fly to Chicago Midway International Airport

    1. Drive from Roseburg to Eugene-Airport-EUGcar car
    2. Fly from Mahlon Sweet Field Airport (EUG) to Chicago Midway International Airport (MDW)plane plane EUG - MDW
    8h 4m
    $146–575

  5. Bus, taxi, train

    1. Take the bus from SE Washington Ave & SE Rose St to Seven Feathers Truck & Travel Centerbus bus
    2. Take the taxi from Seven Feathers Truck & Travel Center to Grants Passtaxi taxi
    3. Take the bus from Grants Pass to Olympiabus bus
    4. Take the bus from Olympia to Spokane Stationbus bus
    5. Take the train from Spokane to Chicago Union Stationtrain train
    2d 9h
    $846–1,681

Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD) flights

Calendar74Weekly Planes
Duration6h 55mAverage Duration
Ticket$108Cheapest Price
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Questions & Answers

Map of how to get from Roseburg to Chicago.ExpandLaunch map view
  • Distance: 1,867 mi
  • Duration: 6h 27m

What companies run services between Roseburg, OR, USA and Chicago, IL, USA?

There is no direct connection from Roseburg to Chicago. However, you can drive to Eugene-Airport-EUG airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can take a vehicle from Roseburg to Chicago Union Station via Eugene and Portland in around 2d 2h.

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