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How to get fromPortland to Chicago Union Stationby plane, bus (Flixbus, Greyhound), train (Amtrak), car or train

Find Transport to Chicago Union Station

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There are 6 ways to get from Portland to Chicago Union Station by plane, bus (Flixbus, Greyhound), train (Amtrak), 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 Portland International Airport to Chicago Midway International Airport

    best
    1. Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)plane plane PDX - MDW
    6h 11m
    $205–908

  2. Fly Portland International Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)plane plane PDX - ORD
    6h 28m
    $115–558

  3. Bus

    1. Take the bus from Portland Curbside Bus Stop to Spokane Stationbus bus
    2. Take the bus from Spokane to Billingsbus bus
    3. Take the bus from Billings to Dickinsonbus bus
    4. Take the bus from Dickinson to Minneapolisbus bus
    5. Take the bus from Minneapolis Bus Station to Chicago Bus Stationbus bus
    45h 54m
    $230–745

  4. Train (Amtrak)

    1. Take the train from Portland to Chicago Union Stationtrain train Empire Builder
    46h
    $550–1,300

  5. Drive 2,076.5 mi

    1. Drive from Portland to Chicago Union Stationcar car 2,076.5 mi
    33h 40m
    $379–548

  6. Train to Mahlon Sweet Field Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Portland to Eugenetrain train
    2. Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)plane plane EUG - ORD
    8h 46m
    $165–576

Portland to Chicago Union Station by bus and foot

Calendar4Weekly Services
Duration45h 54mAverage Duration
Ticket$230Cheapest Price
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Questions & Answers

What companies run services between Portland, OR, USA and Chicago Union Station, IL, USA?

Southwest Airlines and Delta fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, you can take a bus from Portland Curbside Bus Stop to Chicago Union Station via Spokane, Billings, Dickinson, Minneapolis Bus Station, and Chicago Bus Station in around 45h 54m.

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Need to know: Greyhound

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