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How to get fromWalpole to Chicagoby train, plane, train (Amtrak), bus (Flixbus), car or bus

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

    best
    1. Take the train from Walpole to South Stationtrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 46m
    $98–541

  2. Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    7h 45m
    $55–289

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    23h 52m
    $293–659

  4. Bus

    1. Take the bus from Boston, MA - 177 Huntington Ave to Times Square – 37th St.bus bus Boston
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    27h 48m
    $149–279

  5. Drive 976.3 mi

    1. Drive from Walpole to Chicagocar car 976.3 mi
    16h 47m
    $179–258

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

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 5m
    $158–451

  7. Bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    7h 9m
    $135–731

  8. Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 13m
    $90–469

  9. Fly Boston Logan Airport to General Mitchell International Airport, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 5m
    $182–955

Walpole to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration23h 52mAverage Duration
Ticket$293Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $290–650 and the journey takes 22h 15m. Alternatively, you can take a bus from Main St @ Stone St to Chicago Bus Station via Forest Hills, Huntington Ave @ Prudential Station, Boston, MA - 177 Huntington Ave, Times Square – 37th St., and New York Midtown in around 27h 48m.

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