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

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There are 6 ways to get from Portland to Chicago by plane, bus (Amtrak, Greyhound), bus, train, car, or bus (Flixbus)

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
    $105–533

  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 40m
    $84–424

  3. Bus via Brook Park

    1. Take the bus from Portland, ME to Boston, MA - South Stationbus bus
    2. Take the bus from Boston to Cleveland Bus Stationbus bus
    3. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    25h 10m
    $171–298

  4. Bus, train

    1. Take the bus from Portland, ME to Boston, MA - South Stationbus bus Portland / ...
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    25h 17m
    $261–643

  5. Drive  1,036.3 mi

    1. Drive from Portland to Chicagocar car 1,036.3 mi
    19h 16m
    $190–274

  6. Bus (Flixbus)

    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 N2640 / ...
    28h 41m
    $191–305

Portland to Chicago by bus

Calendar7Weekly Buses
Duration25h 10mAverage Duration
Ticket$171Cheapest Price
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Comparing Your Travel Options

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

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

Southwest Airlines flies from Portland (PWM) to Chicago Midway International Airport (MDW) 3 times a day. Alternatively, you can take a bus from Portland, ME to Chicago Bus Station via Boston, MA - South Station, Boston, and Cleveland Bus Station in around 25h 10m.

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