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

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There are 7 ways to get from Portland, ME to Chicago by plane, bus, train, bus (Amtrak, 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 Portland to Chicago Midway International Airport

    best
    1. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    4h 1m
    $158–816

  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 27m
    $94–483

  3. 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
    $311–693

  4. 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 34m
    $178–323

  5. Drive 1,035.5 mi

    1. Drive from Portland, ME to Chicagocar car 1,035.5 mi
    19h 11m
    $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 23m
    $115–534

  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 43m
    $175–444

Portland, ME to Chicago by bus and train

Calendar7Weekly Services
Duration25h 17mAverage Duration
Ticket$311Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Portland (PWM) to Chicago Midway International Airport (MDW) twice daily. Alternatively, you can take a bus from Portland, ME to Chicago Bus Station via Boston, MA - South Station, Boston, and New York Midtown in around 28h 34m.

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