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

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There are 9 ways to get from Chicago to Walpole by plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, 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 Midway International Airport to Boston Logan Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    5h 50m
    $124–673

  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 TF Green Airport to Readvilletrain train
    7h 41m
    $64–327

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    23h 41m
    $232–525

  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
    $143–276

  5. Drive 976.2 mi

    1. Drive from Chicago to Walpolecar car 976.2 mi
    16h 47m
    $179–258

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

    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
    $154–403

  7. 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 TF Green Airport to Readvilletrain train
    7h 11m
    $94–497

  8. 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 45m
    $134–730

  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 32m
    $118–648

Chicago to Walpole by train (Amtrak)

Calendar7Weekly Trains
Duration23h 41mAverage Duration
Ticket$232Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS) 5 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $220–550 and the journey takes 22h 2m.

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