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

Find Transport to Kittery

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There are 10 ways to get from Chicago to Kittery by plane, bus, train, 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 O'Hare International Airport to Boston Logan Airport, bus

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)planeORD - BOS
    2. Take the bus from Boston to Portsmouth Bus Stopbus
    7h 56m
    $118–389

  2. Fly Chicago O'Hare International Airport to Manchester Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)planeORD - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus
    3. Take the bus from Boston to Portsmouth Bus Stopbus
    9h 59m
    $116–537

  3. Train, bus

    1. Take the train from Chicago Union Station to BostontrainLake Shore Limited
    2. Take the bus from Boston to Portsmouth Bus StopbusGreyhound US0265s
    25h 25m
    $118–579

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus
    2. Take the bus from New York Midtown to Bostonbus
    3. Take the bus from Boston to Portsmouth Bus Stopbus
    28h 49m
    $146–359

  5. Drive 998.8 mi

    1. Drive from Chicago to Kitterycar998.8 mi
    18h 14m
    $183–264

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

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)planeMDW - BOS
    2. Take the bus from Boston to Portsmouth Bus Stopbus
    7h 35m
    $118–629

  7. Fly Chicago O'Hare International Airport to Portland, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)planeORD - PWM
    2. Take the bus from City of Portland to Portsmouth Bus Stopbus
    8h 32m
    $126–556

  8. Fly Chicago Midway International Airport to Portland, bus

    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)planeMDW - PWM
    2. Take the bus from City of Portland to Portsmouth Bus Stopbus
    8h 5m
    $150–716

  9. Fly Chicago Midway International Airport to Manchester Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)planeMDW - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus
    3. Take the bus from Boston to Portsmouth Bus Stopbus
    9h 29m
    $140–687

  10. Fly Chicago Midway International Airport to Bradley International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)planeMDW - BDL
    2. Take the bus from Hartford Union Station to Bostonbus
    3. Take the bus from Boston to Portsmouth Bus Stopbus
    10h 21m
    $140–701

Chicago to Kittery by train and bus

Calendar7Weekly Services
Duration25h 25mAverage Duration
Ticket$118Cheapest Price
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Questions & Answers

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

You can take a bus from Chicago Bus Station to Government St. via New York Midtown, Boston, Portsmouth Bus Stop, and Hanover Station in around 28h 49m.

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