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How to get fromChicago to Pittsfieldby plane, bus, train (Amtrak), bus (Flixbus, Greyhound), car or train

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There are 8 ways to get from Chicago to Pittsfield by plane, bus, train (Amtrak), bus (Flixbus, Greyhound), 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. Fly Chicago O'Hare International Airport to Albany County Airport, bus

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    6h 58m
    $106–514

  2. Train (Amtrak)

    cheapest
    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    18h
    $85–280

  3. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Port Authority Bus Terminalbus bus 108
    3. Take the bus from Port Authority Bus Terminal to Pittsfieldbus bus
    25h 30m
    $127–262

  4. Drive 851.9 mi

    1. Drive from Chicago to Pittsfieldcar car 851.9 mi
    14h 44m
    $156–225

  5. Fly Chicago Midway International Airport to Albany County Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    6h 31m
    $146–724

  6. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Springfield to Pittsfield Amtrak Stationtrain train
    7h 39m
    $126–928

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Springfield to Pittsfield Amtrak Stationtrain train
    8h 10m
    $96–728

  8. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Pittsfield Amtrak Stationtrain train
    9h 11m
    $136–581

Chicago to Pittsfield by train (Amtrak)

Calendar7Weekly Trains
Duration18hAverage Duration
Ticket$85Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Chicago Union Station to Pittsfield Amtrak Station once daily. Tickets cost $85–280 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Pittsfield via Newark Penn Station and Port Authority Bus Terminal in around 25h 30m.

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