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How to get fromChicago to Kennebunkby plane, train, bus, bus (Flixbus, Greyhound) or car

Find Transport to Kennebunk

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There are 6 ways to get from Chicago to Kennebunk by plane, train, bus, bus (Flixbus, Greyhound), 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 Chicago Midway International Airport to Portland

    best
    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    4h 16m
    $192–705

  2. Fly Chicago O'Hare International Airport to Portland

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    4h 40m
    $158–515

  3. Train, bus

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the bus from Boston to Wells Transportation Centerbus bus Greyhound US0265s
    24h 54m
    $310–648

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York Midtown to Bostonbus bus
    3. Take the bus from Boston to Wells Transportation Centerbus bus
    28h 16m
    $185–310

  5. Drive 1,013.3 mi

    1. Drive from Chicago to Kennebunkcar car 1,013.3 mi
    18h 48m
    $185–268

  6. Fly Chicago Midway International Airport to Boston Logan Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the train from Woburn Amtrak Station to Wellstrain train
    7h 18m
    $164–688

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

Calendar19Weekly Planes
Duration4h 10mAverage Duration
Ticket$113Cheapest Price
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Questions & Answers

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Portland (PWM) 3 times a day. Alternatively, you can take a bus from Chicago Bus Station to Kennebunk via New York Midtown, Boston, and Wells Transportation Center in around 28h 16m.

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