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How to get fromPortland to Chicagoby taxi, plane, bus (Greyhound), bus, train, car, or bus (Amtrak)

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There are 8 ways to get from Portland to Chicago by taxi, plane, bus (Greyhound), bus, train, car, or bus (Amtrak)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Taxi to Nashville, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Portland to Nashville-Airport-BNAtaxi taxi
    2. Fly from Nashville (BNA) to Chicago Midway International Airport (MDW)plane plane BNA - MDW
    3h 3m
    $197–578

  2. Drive to Owensboro–Daviess County Regional Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from Portland to Owensboro–Daviess County Regional Airport (OWB)car car
    2. Fly from Owensboro–Daviess County Regional Airport (OWB) to Chicago O'Hare International Airport (ORD)plane plane OWB - ORD
    4h 21m
    $55–281

  3. Bus via Speedway

    1. Take the bus from Shell Gas Station - Exit 6 to Indianapolisbus bus Memphis
    2. Take the bus from Indianapolis Union Station to Chicago Bus Stationbus bus Greyhound US0100 / ...
    10h 37m
    $119–171

  4. Taxi, bus, train

    1. Take the taxi from Portland to Clarksville Park & Ridetaxi taxi
    2. Take the bus from Clarksville Park & Ride to Carbondale Intermodal Stationbus bus
    3. Take the train from Carbondale to Chicago Union Stationtrain train
    10h 44m
    $334–463

  5. Drive  435.6 mi

    1. Drive from Portland to Chicagocar car 435.6 mi
    7h 21m
    $75–108

  6. Taxi to Nashville, fly to Chicago O'Hare International Airport

    1. Take the taxi from Portland to Nashville-Airport-BNAtaxi taxi
    2. Fly from Nashville (BNA) to Chicago O'Hare International Airport (ORD)plane plane BNA - ORD
    3h 34m
    $232–428

  7. Bus

    1. Take the bus from Shell Gas Station - Exit 6 to La Tropicana - Louisville, KYbus bus Memphis
    2. Take the bus from Louisville, KY to Chicago Union Stationbus bus Nashville
    11h 45m
    $114–157

  8. Bus, train

    1. Take the bus from Shell Gas Station - Exit 6 to Indianapolisbus bus Memphis
    2. Take the train from Indianapolis to Chicago Union Stationtrain train Cardinal
    12h 2m
    $189–291

Nashville (BNA) to Chicago Midway International Airport (MDW) flights

Calendar34Weekly Planes
Duration1h 48mAverage Duration
Ticket$68Cheapest Price
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Comparing Your Travel Options

Map of how to get from Portland to Chicago.ExpandLaunch map view
  • Distance: 449.5 mi
  • Duration: 3h 3m

What companies run services between Portland, TN, USA and Chicago, IL, USA?

You can take a vehicle from Portland to Chicago Bus Station via Shell Gas Station - Exit 6, Indianapolis, Lafayette Rd & Office Plaza Blvd, Ctc-R, and Indianapolis Union Station in around 10h 37m.

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