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

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

    best
    1. Fly from Roberts Field-Redmond Municipal Airport (RDM) to Chicago O'Hare International Airport (ORD)plane plane RDM - ORD
    8h 23m
    $77–350

  2. Bus, train

    1. Take the bus from Redmond Transit Center to Portland Union Stationbus bus Bend to Portland Express
    2. Take the train from Portland to Chicago Union Stationtrain train Empire Builder
    2d 4h
    $573–1,371

  3. Bus

    1. Take the bus from Redmond Transit Center to Portland Union Stationbus bus
    2. Take the bus from Portland Curbside Bus Stop 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 7h
    $383–661

  4. Drive  1,995.5 mi

    1. Drive from Redmond to Chicagocar car 1,995.5 mi
    32h 33m
    $365–526

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

    1. Take the bus from Redmond Hub to Cleveland Avenue MAX Station, Greshambus bus
    2. Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)plane plane PDX - ORD
    9h 32m
    $234–370

  6. Bus to Portland International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Redmond Hub to Cleveland Avenue MAX Station, Greshambus bus
    2. Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)plane plane PDX - MDW
    9h 22m
    $164–530

  7. Fly Roberts Field-Redmond Municipal Airport to General Mitchell International Airport, train

    1. Fly from Roberts Field-Redmond Municipal Airport (RDM) to General Mitchell International Airport (MKE)plane plane RDM - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 46m
    $163–719

Redmond to Chicago by bus and train

Calendar7Weekly Services
Duration2d 4hAverage Duration
Ticket$573Cheapest Price
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Comparing Your Travel Options

Map of how to get from Redmond to Chicago.ExpandLaunch map view
  • Distance: 1,695.4 mi
  • Duration: 8h 23m

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

United Airlines, Alaska Airlines, Inc., and two other airlines fly from Roberts Field-Redmond Municipal Airport (RDM) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a bus from Redmond Transit Center to Chicago Bus Station via Portland Union Station, Portland Curbside Bus Stop, Pasco Bus Stop, and Denver Union Station in around 2d 7h.

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