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

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There are 7 ways to get from Pittsfield to Chicago by bus, plane, train (Amtrak), bus (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
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)planeALB - MDW
    6h 5m
    $118–576

  2. Train to Bradley International Airport, fly to Chicago Midway International Airport

    cheapest
    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)planeBDL - MDW
    7h 19m
    $109–715

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union StationtrainLake Shore Limited
    18h 30m
    $220–300

  4. Bus

    1. Take the bus from Pittsfield to Port Authority Bus TerminalbusWilliamstown
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    25h 36m
    $110–285

  5. Drive 851.5 mi

    1. Drive from Pittsfield to Chicagocar851.5 mi
    14h 35m
    $156–225

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

    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)planeALB - ORD
    6h 42m
    $218–576

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

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)planeBDL - ORD
    7h 45m
    $389–935

Pittsfield to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration18h 30mAverage Duration
Ticket$220Cheapest Price
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Questions & Answers

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 $220–300 and the journey takes 18h 30m. Alternatively, you can take a bus from Pittsfield to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 25h 36m.

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