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

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There are 7 ways to get from Pittsfield to Chicago by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, 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. Bus to Albany County Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    6h 17m
    $143–722

  2. Bus to Albany County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    6h 45m
    $103–522

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    18h 30m
    $470–750

  4. Bus

    1. Take the bus from Pittsfield to New Yorkbus bus
    2. Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus bus
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    25h 18m
    $187–309

  5. Drive  850.7 mi

    1. Drive from Pittsfield to Chicagocar car 850.7 mi
    14h 44m
    $146–210

  6. Train, train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Take the train from Springfield to Hartford Amtrak Stationtrain train
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 56m
    $137–563

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

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Take the train from Springfield to Hartford Amtrak Stationtrain train
    3. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    8h 25m
    $112–423

Pittsfield to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration18h 30mAverage Duration
Ticket$470Cheapest Price
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Comparing Your Travel Options

Map of how to get from Pittsfield to Chicago.ExpandLaunch map view
  • Distance: 773 mi
  • Duration: 6h 17m

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

Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily. Tickets cost $470–750 and the journey takes 18h 30m. Alternatively, you can take a bus from Pittsfield to Chicago Bus Station via New York, Port Authority Bus Terminal, and Newark Penn Station in around 25h 18m.

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