Rome2Rio

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

Find Transport to Chicago

See all options

There are 9 ways to get from Walpole to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), 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 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 10m
    $117–441

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

    cheapest
    1. Take the train from Boston to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    7h 19m
    $62–886

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h
    $143–759

  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 10m
    $119–339

  5. Drive 976.3 mi

    1. Drive from Walpole to Chicagocar car 976.3 mi
    16h 46m
    $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 55m
    $97–511

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

    1. Take the train from Boston to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    6h 56m
    $82–1,006

  8. 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 18m
    $129–649

  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 55m
    $309–756

Walpole to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration24hAverage Duration
Ticket$143Cheapest Price
See schedules

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 $140–750 and the journey takes 22h 15m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Where to next?

Trips from Walpole

Trips to Chicago

Popular routes