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How to get fromWinnetka to Portlandby plane, train (Amtrak), car or train

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There are 5 ways to get from Winnetka to Portland by plane, 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 from Chicago Midway International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)plane plane MDW - PDX
    7h 45m
    $259–1,213

  2. Fly from Chicago O'Hare International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX)plane plane ORD - PDX
    7h 49m
    $180–814

  3. Train (Amtrak)

    1. Take the train from Glenview Amtrak Station to Portlandtrain train Empire Builder
    47h 17m
    $602–1,403

  4. Drive 2,056.4 mi

    1. Drive from Winnetka to Portlandcar car 2,056.4 mi
    33h 52m
    $376–543

  5. Train to General Mitchell International Airport, fly

    1. Take the train from Glenview Amtrak Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Portland International Airport (PDX)plane plane MKE - PDX
    10h 58m
    $375–1,660

Winnetka to Portland by bus and train (Amtrak)

Calendar11Weekly Services
Duration47h 17mAverage Duration
Ticket$602Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) 5 times a day. Alternatively, Amtrak operates a train from Glenview Amtrak Station to Portland twice daily. Tickets cost $600–1,400 and the journey takes 45h 48m.

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