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

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There are 6 ways to get from Portland to Chicago by plane, train (Amtrak), bus (Flixbus, Greyhound), 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 O'Hare International Airport

    best
    1. Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)plane plane PDX - ORD
    6h 19m
    $145–658

  2. Train (Amtrak)

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

  3. Bus

    1. Take the bus from Portland Curbside Bus Stop to Pasco Bus Stopbus bus
    2. Take the bus from Pasco Bus Stop to Denver Union Stationbus bus
    3. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    2d
    $368–726

  4. Drive 2,077.3 mi

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

  5. Fly Portland International Airport to Chicago Midway International Airport

    1. Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)plane plane PDX - MDW
    6h 6m
    $185–808

  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 33m
    $196–667

Portland to Chicago by train (Amtrak)

Calendar11Weekly Trains
Duration46hAverage Duration
Ticket$600Cheapest Price
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Questions & Answers

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

American Airlines, Alaska Airlines, Inc., and three other airlines fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Amtrak operates a train from Portland to Chicago Union Station twice daily. Tickets cost $600–1,400 and the journey takes 46h.

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