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

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There are 7 ways to get from Greenfield to Chicago by train, plane, train (Amtrak), bus (Greyhound, 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 Bradley International Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Greenfield Amtrak Station to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    6h 20m
    $94–441

  2. Train to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Greenfield Amtrak Station to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    6h 54m
    $84–381

  3. Train (Amtrak)

    1. Take the train from Greenfield Amtrak Station to Springfieldtrain train Valley Flyer / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    21h 54m
    $302–674

  4. Bus

    1. Take the bus from Greenfield John Olver Transit Ctr to Springfield Union Stationbus bus
    2. Take the bus from Springfield Union Station to Newark Penn Stationbus bus
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    22h 45m
    $166–301

  5. Drive 884.1 mi

    1. Drive from Greenfield to Chicagocar car 884.1 mi
    16h
    $162–234

  6. Train, bus to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the train from Greenfield Amtrak Station to Springfieldtrain train
    2. Take the bus from Springfield Union Station to Albany Bus Terminal, NYbus bus
    3. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    8h 31m
    $140–657

  7. Train, bus to Albany County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Greenfield Amtrak Station to Springfieldtrain train
    2. Take the bus from Springfield Union Station to Albany Bus Terminal, NYbus bus
    3. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    9h
    $125–537

Greenfield to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration21h 54mAverage Duration
Ticket$302Cheapest Price
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Questions & Answers

Map of how to get from Greenfield to Chicago.ExpandLaunch map view
  • Distance: 839.7 mi
  • Duration: 6h 20m

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

You can take a train from Greenfield Amtrak Station to Chicago Union Station via Springfield in around 21h 54m. Alternatively, you can take a bus from Greenfield John Olver Transit Ctr to Chicago Bus Station via Springfield Union Station and Newark Penn Station in around 22h 45m.

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