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

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There are 6 ways to get from Portland to Chicago 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 1m
    $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 14m
    $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 45m
    $231–747

  4. Train (Amtrak)

    1. Take the train from Portland to Chicago Union Stationtrain train Empire Builder
    46h
    $600–1,400

  5. Drive 2,077.3 mi

    1. Drive from Portland to Chicagocar car 2,077.3 mi
    33h 41m
    $380–548

  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 32m
    $166–577

Portland to Chicago by bus

Calendar4Weekly Buses
Duration45h 45mAverage Duration
Ticket$231Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from Portland Curbside Bus Stop to Chicago Bus Station via Spokane, Billings, Dickinson, and Minneapolis Bus Station in around 45h 45m.

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