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

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There are 11 ways to get from Chicago to Kittery by plane, bus, train, bus (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 Chicago Midway International Airport to Boston Logan Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the bus from Boston to Portsmouthbus bus
    7h 42m
    $120–580

  2. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train, bus

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from TF Green Airport to South Stationtrain train
    3. Take the bus from Boston to Portsmouth Bus Stopbus bus
    9h 33m
    $90–419

  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 FlixBus N2615
    25h 10m
    $281–616

  4. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from New York Midtown to Portsmouth Bus Stopbus bus FlixBus N2615
    25h 24m
    $166–265

  5. Drive  998.2 mi

    1. Drive from Chicago to Kitterycar car 998.2 mi
    18h 25m
    $183–264

  6. Fly Chicago O'Hare International Airport to Boston Logan Airport, bus

    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 Portsmouthbus bus
    8h 2m
    $620–1,030

  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
    7h 50m
    $134–675

  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 19m
    $104–485

  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 17m
    $118–587

  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
    9h 52m
    $94–427

  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 14m
    $136–654

Chicago to Kittery by train and bus

Calendar7Weekly Services
Duration25h 10mAverage Duration
Ticket$281Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Kittery.ExpandLaunch map view
  • Distance: 927.9 mi
  • Duration: 7h 42m

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, Portsmouth Bus Stop, and Hanover Station in around 25h 24m.

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