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

Find Transport to Chicago

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There are 5 ways to get from Kennebunk to Chicago by plane, bus, train, bus (Greyhound, 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 to Chicago Midway International Airport

    best
    1. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)planePWM - MDW
    3h 45m
    $193–651

  2. Bus

    cheapest
    1. Take the bus from Wells Transportation Center to Bostonbus
    2. Take the bus from Boston to New York Midtownbus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus
    28h 49m
    $161–336

  3. Bus, train

    1. Take the bus from Wells Transportation Center to BostonbusGreyhound US0265s
    2. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    25h 29m
    $181–756

  4. Drive 1,014.1 mi

    1. Drive from Kennebunk to Chicagocar1,014.1 mi
    18h 39m
    $186–268

  5. Fly to Chicago O'Hare International Airport

    1. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)planePWM - ORD
    4h 23m
    $163–511

Portland (PWM) to Chicago Midway International Airport (MDW) flights

Calendar12Weekly Planes
Duration4h 59mAverage Duration
Ticket$110Cheapest Price
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Questions & Answers

What companies run services between Kennebunk, 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 vehicle from Kennebunk to Chicago Bus Station via Wells Transportation Center, Boston, and New York Midtown in around 28h 49m.

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