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How to get fromRoseburg to Chicagoby bus, plane, train, bus (Flixbus, Greyhound), or car

Find Transport to Chicago

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There are 7 ways to get from Roseburg to Chicago by bus, plane, train, bus (Flixbus, Greyhound), 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. Bus to Mahlon Sweet Field Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from NE Jackson St. to Eugene U of Obus bus
    2. Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)plane plane EUG - ORD
    8h 46m
    $91–398

  2. Bus, train

    1. Take the bus from NE Jackson St. to Eugene Amtrakbus bus
    2. Take the train from Eugene to Portlandtrain train
    3. Take the train from Portland to Chicago Union Stationtrain train
    2d 4h
    $588–1,502

  3. Bus

    1. Take the bus from NE Jackson St. to Eugene U of Obus bus
    2. Take the bus from Eugene to Pasco Bus Stopbus bus
    3. Take the bus from Pasco Bus Stop to Denver Union Stationbus bus
    4. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    2d 6h
    $398–641

  4. Drive  2,146.7 mi

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

  5. Bus to Mahlon Sweet Field Airport, fly to Chicago Midway International Airport

    1. Take the bus from NE Jackson St. to Eugene U of Obus bus
    2. Fly from Mahlon Sweet Field Airport (EUG) to Chicago Midway International Airport (MDW)plane plane EUG - MDW
    10h 46m
    $111–508

  6. Bus, train to Portland International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from NE Jackson St. to Eugene Amtrakbus bus
    2. Take the train from Eugene to Portlandtrain train
    3. Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)plane plane PDX - ORD
    11h 51m
    $213–410

  7. Bus, train to Portland International Airport, fly to Chicago Midway International Airport

    1. Take the bus from NE Jackson St. to Eugene Amtrakbus bus
    2. Take the train from Eugene to Portlandtrain train
    3. Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)plane plane PDX - MDW
    11h 40m
    $143–570

Roseburg to Chicago by bus and train

Calendar7Weekly Services
Duration2d 4hAverage Duration
Ticket$588Cheapest Price
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Comparing Your Travel Options

Map of how to get from Roseburg to Chicago.ExpandLaunch map view
  • Distance: 1,875.3 mi
  • Duration: 8h 46m

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

You can take a bus from NE Jackson St. to Chicago Bus Station via Eugene, Pasco Bus Stop, and Denver Union Station in around 2d 6h.

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