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

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

    best
    1. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    3h 55m
    $106–521

  2. Fly Portland to Chicago O'Hare International Airport

    cheapest
    1. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane plane PWM - ORD
    4h 22m
    $88–432

  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
    $281–643

  5. Drive  1,034.7 mi

    1. Drive from Portland, ME to Chicagocar car 1,034.7 mi
    19h 13m
    $189–273

  6. Bus to Boston Logan Airport, fly to Chicago Midway International Airport

    1. Take the bus from Portland, ME to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    6h 18m
    $111–476

  7. Bus to Boston Logan Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Portland, ME to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 34m
    $626–936

  8. Bus

    1. Take the bus from Portland, ME to Boston, MA - South Stationbus bus
    2. Take the bus from Boston to New York Midtownbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    28h 40m
    $191–323

Portland, ME 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, ME to Chicago.ExpandLaunch map view
  • Distance: 905.7 mi
  • Duration: 3h 55m

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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