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How to get fromKennebunk to ChicagoBy plane, train (Amtrak), bus (Greyhound), car, or bus (Flixbus)

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There are 6 ways to get from Kennebunk to Chicago by plane, train (Amtrak), bus (Greyhound), 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 O'Hare International Airport

    best
    1. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane plane PWM - ORD
    4h 11m
    $193–701

  2. Bus (Flixbus)

    cheapest
    1. Take the bus from Portsmouth Bus Stop to New York Midtownbus bus FlixBus N2615
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    25h 57m
    $172–300

  3. Train (Amtrak)

    1. Take the train from Wells to Bostontrain train Downeaster
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    25h 30m
    $319–681

  4. Bus via Brook Park (Greyhound)

    1. Take the bus from Wells Transportation Center to Bostonbus 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 37m
    $191–373

  5. Drive 1,013.4 mi

    1. Drive from Kennebunk to Chicagocar car 1,013.4 mi
    18h 50m
    $185–268

  6. Fly to Chicago Midway International Airport

    1. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    3h 45m
    $223–851

Portland (PWM) to Chicago O'Hare International Airport (ORD) flights

Calendar85Weekly Planes
Duration3h 20mAverage Duration
Ticket$112Cheapest Price
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Questions & Answers

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

American Airlines, United Airlines, and Delta fly from Portland (PWM) to Chicago O'Hare International Airport (ORD) every 2 hours. Alternatively, you can take a vehicle from Kennebunk to Chicago Union Station via Wells, Boston, North Station, Back Bay, and Boston in around 25h 30m.

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Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

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