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

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There are 9 ways to get from Walpole to Chicago by plane, train (Amtrak), bus (Greyhound, 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 O'Hare International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 11m
    $127–421

  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
    $55–269

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    23h 52m
    $103–709

  4. Bus

    1. Take the bus from Boston, MA to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus bus 108
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    28h 13m
    $118–309

  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 Midway International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 56m
    $92–501

  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 19m
    $119–584

  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 23m
    $75–379

  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
    $179–1,006

Walpole to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration23h 52mAverage Duration
Ticket$103Cheapest Price
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Questions & Answers

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

American Airlines, JetBlue Airways, and two other airlines fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $100–700 and the journey takes 22h 15m.

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