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

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There are 10 ways to get from Walpole to Chicago by plane, train (Amtrak), bus (Flixbus), car, bus, or train

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 Boston Logan Airport to Chicago Midway International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 37m
    $88–461

  2. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    23h 52m
    $283–659

  3. Bus

    1. Take the bus from Boston, MA - Dalton and Belvidere Street to New York, NY - W 42nd Street and 9th Avenuebus bus Boston
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    24h 33m
    $177–374

  4. Drive 975.6 mi

    1. Drive from Walpole to Chicagocar car 975.6 mi
    16h 49m
    $178–258

  5. 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
    5h 54m
    $208–591

  6. 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
    $114–580

  7. 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 19m
    $99–479

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

    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 46m
    $89–419

  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
    7h 56m
    $161–805

  10. Bus to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Boston to Hartford Union Stationbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    8h 24m
    $105–513

Walpole to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration23h 52mAverage Duration
Ticket$283Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $280–650 and the journey takes 22h 15m.

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