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How to get fromChicago to Prinevilleby plane, train, bus, or car

Find Transport to Prineville

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There are 7 ways to get from Chicago to Prineville by plane, train, bus, 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 O'Hare International Airport to Roberts Field-Redmond Municipal Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Roberts Field-Redmond Municipal Airport (RDM)plane plane ORD - RDM
    10h 48m
    $96–403

  2. Train, bus

    1. Take the train from Chicago Union Station to Portlandtrain train Empire Builder
    2. Take the bus from Portland Union Station to Redmond Transit Centerbus bus Bend to Portland Express
    2d 5h
    $1,263–1,988

  3. Drive  1,976.1 mi

    1. Drive from Chicago to Prinevillecar car 1,976.1 mi
    32h 6m
    $361–521

  4. Fly Chicago Midway International Airport to Portland International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)plane plane MDW - PDX
    2. Take the bus from Portland International Airport to Redmond Hubbus bus
    11h 53m
    $212–769

  5. Train to General Mitchell International Airport, fly to Roberts Field-Redmond Municipal Airport

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Roberts Field-Redmond Municipal Airport (RDM)plane plane MKE - RDM
    12h 16m
    $193–744

  6. Fly Chicago O'Hare International Airport to Portland International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX)plane plane ORD - PDX
    2. Take the bus from Portland International Airport to Redmond Hubbus bus
    12h 16m
    $232–369

  7. Fly Chicago Midway International Airport to Roberts Field-Redmond Municipal Airport

    1. Fly from Chicago Midway International Airport (MDW) to Roberts Field-Redmond Municipal Airport (RDM)plane plane MDW - RDM
    10h 32m
    $136–613

Chicago to Prineville by train and bus

Calendar7Weekly Services
Duration2d 5hAverage Duration
Ticket$1,263Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Prineville.ExpandLaunch map view
  • Distance: 1,712.7 mi
  • Duration: 10h 48m

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

United Airlines, Alaska Airlines, Inc., and two other airlines fly from Chicago O'Hare International Airport (ORD) to Roberts Field-Redmond Municipal Airport (RDM) hourly.

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