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

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There are 11 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)plane plane ORD - BOS
    2. Take the bus from Boston to Portsmouth Bus Stopbus bus
    7h 50m
    $144–432

  2. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the train from TF Green Airport to South Stationtrain train
    3. Take the bus from Boston to Portsmouth Bus Stopbus bus
    10h 10m
    $70–321

  3. Train, bus

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the bus from Boston to Portsmouth Bus Stopbus bus Greyhound US0265s
    25h 25m
    $240–539

  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 Portsmouth Bus Stopbus bus
    28h 46m
    $154–264

  5. Drive 998.9 mi

    1. Drive from Chicago to Kitterycar car 998.9 mi
    18h 24m
    $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)plane plane MDW - BOS
    2. Take the bus from Boston to Portsmouth Bus Stopbus bus
    7h 30m
    $124–702

  7. Fly Chicago Midway International Airport to Portland, bus

    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    2. Take the bus from City of Portland to Portsmouth Bus Stopbus bus
    8h 5m
    $124–677

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    2. Take the bus from City of Portland to Portsmouth Bus Stopbus bus
    8h 29m
    $90–447

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

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the bus from Boston to Portsmouth Bus Stopbus bus
    9h 29m
    $142–741

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane plane ORD - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the bus from Boston to Portsmouth Bus Stopbus bus
    10h 8m
    $106–501

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

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Hartford Union Station to Bostonbus bus
    3. Take the bus from Boston to Portsmouth Bus Stopbus bus
    10h 15m
    $126–664

Chicago to Kittery by train and bus

Calendar7Weekly Services
Duration25h 25mAverage Duration
Ticket$240Cheapest 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 46m.

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