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How to get fromOregon to Chicagoby plane, train (Amtrak) or car

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There are 7 ways to get from Oregon to Chicago by plane, train (Amtrak), 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 Mahlon Sweet Field Airport to Chicago O'Hare International Airport

    best
    1. Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)plane plane EUG - ORD
    4h 56m
    $207–846

  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 24m
    $135–608

  3. Train (Amtrak)

    1. Take the train from Portland to Chicago Union Stationtrain train Empire Builder
    46h
    $200–1,100

  4. Drive 2,077.3 mi

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

  5. Fly Mahlon Sweet Field Airport to Chicago Midway International Airport

    1. Fly from Mahlon Sweet Field Airport (EUG) to Chicago Midway International Airport (MDW)plane plane EUG - MDW
    6h 38m
    $297–1,246

  6. Fly Rogue Valley International - Medford Airport to Chicago O'Hare International Airport

    1. Fly from Rogue Valley International - Medford Airport (MFR) to Chicago O'Hare International Airport (ORD)plane plane MFR - ORD
    7h 3m
    $155–671

  7. 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 12m
    $185–858

Oregon to Chicago by train (Amtrak)

Calendar11Weekly Trains
Duration46hAverage Duration
Ticket$200Cheapest Price
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Questions & Answers

What companies run services between Oregon, USA and Chicago, IL, USA?

United Airlines, Alaska Airlines, Inc., and three other airlines fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD) every 4 hours. Alternatively, Amtrak operates a train from Portland to Chicago Union Station twice daily. Tickets cost $200–1,100 and the journey takes 46h.

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