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How to get fromKennebunkport to Chicagoby taxi, plane, bus (Greyhound), train (Amtrak), car, or bus (Flixbus)

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There are 6 ways to get from Kennebunkport to Chicago by taxi, plane, bus (Greyhound), train (Amtrak), 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. Taxi, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Kennebunkport to Portland-Airport-PWMtaxi taxi
    2. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    3h 46m
    $188–656

  2. Taxi, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the taxi from Kennebunkport to Portland-Airport-PWMtaxi taxi
    2. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane plane PWM - ORD
    4h 17m
    $178–566

  3. 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 25m
    $180–325

  4. 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 32m
    $325–742

  5. Drive 1,015.5 mi

    1. Drive from Kennebunkport to Chicagocar car 1,015.5 mi
    18h 55m
    $186–268

  6. Bus (Flixbus)

    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 / ...
    26h
    $192–305

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

Calendar14Weekly Planes
Duration4h 1mAverage Duration
Ticket$105Cheapest Price
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Questions & Answers

Map of how to get from Kennebunkport to Chicago.ExpandLaunch map view
  • Distance: 928.7 mi
  • Duration: 3h 46m

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

You can take a vehicle from Kennebunkport to Chicago Bus Station via Wells Transportation Center, Boston, and Cleveland Bus Station in around 25h 25m. Alternatively, you can take a vehicle from Kennebunkport to Chicago Union Station via Wells, Boston, North Station, Back Bay, and Boston in around 25h 32m.

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