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

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There are 8 ways to get from Chicago to Walpole by plane, train, train (Amtrak), bus (Flixbus, Greyhound), car, or bus

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, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)planeORD - BOS
    2. Take the train from Back Bay to Walpoletrain
    6h 8m
    $114–333
  2. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)planeORD - PVD
    2. Take the train from Providence to Readvilletrain
    8h 18m
    $64–311
  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to BostontrainLake Shore Limited
    23h 40m
    $136–671
  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn StationbusFlixBus N2640
    2. Take the bus from Newark Penn Station to BostonbusGreyhound US0235 / ...
    27h 47m
    $151–345
  5. Drive 976.1 mi

    1. Drive from Chicago to Walpolecar976.1 mi
    16h 40m
    $179–258
  6. Fly Chicago Midway International Airport to Boston Logan Airport

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)planeMDW - BOS
    5h 48m
    $104–493
  7. 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
    7h 45m
    $120–600
  8. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)planeMDW - PVD
    2. Take the train from Providence to Readvilletrain
    7h 50m
    $74–361

Chicago to Walpole by train (Amtrak)

Calendar7Weekly Trains
Duration23h 40mAverage Duration
Ticket$136Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Walpole, MA, USA?

Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $130–700 and the journey takes 22h 2m. Alternatively, you can take a bus from Chicago Bus Station to Main St @ Glenwood Ave via Newark Penn Station, Boston, South Station, Forest Hills, and Forest Hills in around 27h 47m.

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