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

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There are 9 ways to get from Chicago to Pittsfield by plane, bus, train (Amtrak), bus (Greyhound), car, train, or bus (Flixbus)

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 Midway International Airport to Albany County Airport, bus

    best
    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 28m
    $152–769

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

    cheapest
    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 20m
    $104–463

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    18h
    $280–600

  4. Bus via Brook Park (Greyhound)

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Albany Bus Terminal, NYbus bus
    3. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    20h 20m
    $132–245

  5. Drive 851.2 mi

    1. Drive from Chicago to Pittsfieldcar car 851.2 mi
    14h 45m
    $156–225

  6. Fly Chicago O'Hare International Airport to Albany County Airport, bus

    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 59m
    $112–619

  7. 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 52m
    $124–603

  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 18m
    $186–791

  9. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to Pittsfieldbus bus New York
    22h 36m
    $158–285

Chicago to Pittsfield by train (Amtrak)

Calendar7Weekly Trains
Duration18hAverage Duration
Ticket$280Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Pittsfield.ExpandLaunch map view
  • Distance: 773.3 mi
  • Duration: 6h 28m

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 $280–600 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Pittsfield via Cleveland Bus Station and Albany Bus Terminal, NY in around 20h 20m.

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