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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 9 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)plane plane ORD - BOS
    2. Take the train from Back Bay to Walpoletrain train
    6h 14m
    $124–343

  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)plane plane ORD - PVD
    2. Take the train from Providence to Back Baytrain train
    8h 3m
    $66–911

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    23h 28m
    $99–574

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus FlixBus N2640
    2. Take the bus from Newark Penn Station to Bostonbus bus Greyhound US0235 / ...
    27h 47m
    $138–319

  5. Drive 976.1 mi

    1. Drive from Chicago to Walpolecar car 976.1 mi
    16h 47m
    $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)plane plane MDW - BOS
    5h 50m
    $114–573

  7. 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
    7h 50m
    $128–635

  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)plane plane MDW - PVD
    2. Take the train from Providence to Back Baytrain train
    7h 43m
    $80–991

  9. 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
    8h 37m
    $138–658

Chicago to Walpole by train (Amtrak)

Calendar7Weekly Trains
Duration23h 28mAverage Duration
Ticket$99Cheapest 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 $95–600 and the journey takes 21h 54m. 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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