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

Find Transport to Chicago

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There are 6 ways to get from Maine 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 O'Hare International Airport

    best
    1. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane plane PWM - ORD
    3h 55m
    $81–414

  2. Fly Bangor to Chicago O'Hare International Airport

    cheapest
    1. Fly from Bangor (BGR) to Chicago O'Hare International Airport (ORD)plane plane BGR - ORD
    4h 58m
    $68–366

  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 54m
    $123–749

  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
    29h 14m
    $143–329

  5. Drive 1,037.1 mi

    1. Drive from Portland to Chicagocar car 1,037.1 mi
    19h 13m
    $190–274

  6. Fly Portland to Chicago Midway International Airport

    1. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    3h 16m
    $115–595

Maine to Chicago by bus and train

Calendar7Weekly Services
Duration25h 54mAverage Duration
Ticket$123Cheapest Price
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Questions & Answers

What companies run services between Maine, USA and Chicago, IL, USA?

American Airlines, United Airlines, and Delta fly from Portland (PWM) to Chicago O'Hare International Airport (ORD) every 4 hours. Alternatively, you can take a bus from Portland Public Library to Chicago Bus Station via Portland, ME, Boston, MA - South Station, Boston, and New York Midtown in around 29h 14m.

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