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How to get fromPortland Union Station to Chicago Union Stationby plane, train (Amtrak), bus (Flixbus, Greyhound), car, or train

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There are 8 ways to get from Portland Union Station to Chicago Union Station 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 Midway International Airport

    best
    1. Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)plane plane PDX - MDW
    6h 33m
    $125–558

  2. Train (Amtrak)

    1. Take the train from Portland to Chicago Union Stationtrain train Empire Builder
    46h
    $700–1,500

  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 1h
    $354–697

  4. Drive 2,076.9 mi

    1. Drive from Portland Union Station to Chicago Union Stationcar car 2,076.9 mi
    33h 42m
    $379–548

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

    1. Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)plane plane PDX - ORD
    6h 43m
    $195–308

  6. Train to Seattle-Tacoma International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Portland to Tacomatrain train
    2. Fly from Seattle-Tacoma International Airport (SEA) to Chicago O'Hare International Airport (ORD)plane plane SEA - ORD
    9h 41m
    $190–380

  7. Train to Seattle-Tacoma International Airport, fly to Chicago Midway International Airport

    1. Take the train from Portland to Tacomatrain train
    2. Fly from Seattle-Tacoma International Airport (SEA) to Chicago Midway International Airport (MDW)plane plane SEA - MDW
    9h 31m
    $160–580

  8. Fly Portland International Airport to General Mitchell International Airport, train

    1. Fly from Portland International Airport (PDX) to General Mitchell International Airport (MKE)plane plane PDX - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 37m
    $212–877

Portland Union Station to Chicago Union Station by train (Amtrak)

Calendar7Weekly Trains
Duration46hAverage Duration
Ticket$700Cheapest Price
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Questions & Answers

Map of how to get from Portland Union Station to Chicago Union Station.ExpandLaunch map view
  • Distance: 1,770.3 mi
  • Duration: 6h 33m

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

Southwest Airlines and Delta fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, Amtrak operates a train from Portland to Chicago Union Station once daily. Tickets cost $700–1,500 and the journey takes 46h.

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