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How to get fromChicago to Milwaukieby plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

Find Transport to Milwaukie

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There are 6 ways to get from Chicago to Milwaukie by plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

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 from Chicago Midway International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)plane plane MDW - PDX
    7h 25m
    $168–761

  2. Train to South Bend, fly

    cheapest
    1. Take the train from Van Buren St. to South Bend Airporttrain train
    2. Fly from South Bend (SBN) to Portland International Airport (PDX)plane plane SBN - PDX
    11h 25m
    $151–622

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Portlandtrain train Empire Builder
    46h 55m
    $1,238–1,898

  4. Bus

    1. Take the bus from Chicago Bus Station to Denver Union Stationbus bus
    2. Take the bus from Denver Union Station to Pasco Bus Stopbus bus
    3. Take the bus from Pasco Bus Stop to Portland Curbside Bus Stopbus bus
    2d 4h
    $415–632

  5. Drive  2,080.1 mi

    1. Drive from Chicago to Milwaukiecar car 2,080.1 mi
    33h 50m
    $380–549

  6. Fly from Chicago O'Hare International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX)plane plane ORD - PDX
    7h 48m
    $178–311

Chicago to Milwaukie by train and tram (Amtrak)

Calendar7Weekly Services
Duration46h 55mAverage Duration
Ticket$1,238Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Milwaukie.ExpandLaunch map view
  • Distance: 1,776.9 mi
  • Duration: 7h 25m

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) 5 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to Portland once daily. Tickets cost $1,200–1,900 and the journey takes 46h 12m.

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Want to know more about travelling around United States

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