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How to get fromPortland Airport (PWM) to Chicagoby plane, bus, train, bus (Flixbus), or car

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There are 5 ways to get from Portland Airport (PWM) to Chicago by plane, bus, train, bus (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 to Chicago Midway International Airport

    best
    1. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    3h 11m
    $106–495

  2. Fly to Chicago O'Hare International Airport

    cheapest
    1. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane plane PWM - ORD
    3h 42m
    $91–422

  3. Bus, train

    1. Take the bus from City of Portland to Springfield Union Stationbus bus FlixBus N2615
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    26h 13m
    $322–659

  4. Bus

    1. Take the bus from City of Portland to New York Midtownbus bus FlixBus N2615
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    26h 32m
    $197–334

  5. Drive 1,034.1 mi

    1. Drive from Portland Airport (PWM) to Chicagocar car 1,034.1 mi
    19h 15m
    $189–273

Portland Airport (PWM) to Chicago by bus and train

Calendar7Weekly Services
Duration26h 13mAverage Duration
Ticket$322Cheapest Price
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Questions & Answers

Map of how to get from Portland Airport (PWM) to Chicago.ExpandLaunch map view
  • Distance: 903.5 mi
  • Duration: 3h 11m

What companies run services between Portland Airport (PWM), USA and Chicago, IL, USA?

Southwest Airlines flies from Portland (PWM) to Chicago Midway International Airport (MDW) twice daily. Alternatively, you can take a bus from Portland Jetport to Chicago Bus Station via City of Portland and New York Midtown in around 26h 32m.

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