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

Find Transport to Oregon

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There are 8 ways to get from Chicago to Oregon by plane, train (Amtrak), bus (Greyhound, Flixbus), 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
    $236–1,008
  2. Fly Chicago O'Hare International Airport to Rogue Valley International - Medford Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Rogue Valley International - Medford Airport (MFR)plane plane ORD - MFR
    9h 55m
    $134–645
  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Portlandtrain train Empire Builder
    46h 12m
    $600–1,300
  4. Bus

    1. Take the bus from Chicago Bus Station to Denver Union Stationbus bus
    2. Take the bus from Denver Union Station to Pasco Bus Stopbus bus
    3. Take the bus from Pasco Bus Stop to Portland Curbside Bus Stopbus bus
    2d 2h
    $370–709
  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
    6h 57m
    $166–758
  7. Fly Chicago O'Hare International Airport to Mahlon Sweet Field Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Mahlon Sweet Field Airport (EUG)plane plane ORD - EUG
    6h 47m
    $212–845
  8. 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
    8h 1m
    $292–1,245

Chicago to Oregon by train (Amtrak)

Calendar11Weekly Trains
Duration46h 12mAverage Duration
Ticket$600Cheapest Price
See schedules

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) 5 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to Portland twice daily. Tickets cost $600–1,300 and the journey takes 46h 12m.

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