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

Find Transport to Oregon

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There are 7 ways to get from Chicago to Oregon by plane, bus (Greyhound, Flixbus), 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 Chicago Midway International Airport to Portland International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)plane plane MDW - PDX
    6h 35m
    $256–1,208

  2. Fly Chicago O'Hare International Airport to Mahlon Sweet Field Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Mahlon Sweet Field Airport (EUG)plane plane ORD - EUG
    6h 48m
    $142–600

  3. Bus

    1. Take the bus from Chicago Bus Station to Minneapolis Bus Stationbus bus
    2. Take the bus from Minneapolis to Dickinsonbus bus
    3. Take the bus from Dickinson to Billingsbus bus
    4. Take the bus from Billings to Spokanebus bus
    5. Take the bus from Spokane Station to Portland Curbside Bus Stopbus bus
    45h 40m
    $232–747

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Portlandtrain train Empire Builder
    46h 12m
    $600–1,400

  5. Drive 2,077 mi

    1. Drive from Chicago to Portlandcar car 2,077 mi
    33h 43m
    $380–548

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX)plane plane ORD - PDX
    7h
    $176–808

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

    1. Fly from Chicago Midway International Airport (MDW) to Mahlon Sweet Field Airport (EUG)plane plane MDW - EUG
    7h 56m
    $202–850

Chicago to Oregon by bus

Calendar4Weekly Buses
Duration45h 40mAverage Duration
Ticket$232Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Portland Curbside Bus Stop via Minneapolis, Dickinson, Billings, and Spokane Station in around 45h 40m.

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