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

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There are 5 ways to get from Berkshires to Chicago by taxi, plane, train (Amtrak), bus (Flixbus), or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Taxi, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Berkshires to Albany-Airport-ALBtaxi taxi
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    4h 19m
    $269–828

  2. Drive 852.8 mi

    cheapest
    1. Drive from Berkshires to Chicagocar car 852.8 mi
    15h 9m
    $156–225

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    19h 13m
    $306–604

  4. Bus

    1. Take the bus from Williamstown to Port Authority Bus Terminalbus bus Williamstown
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2642 / ...
    28h 58m
    $211–352

  5. Taxi, fly to Chicago O'Hare International Airport

    1. Take the taxi from Berkshires to Albany-Airport-ALBtaxi taxi
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    4h 49m
    $239–638

Albany County Airport (ALB) to Chicago Midway International Airport (MDW) flights

Calendar43Weekly Planes
Duration3h 22mAverage Duration
Ticket$126Cheapest Price
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Questions & Answers

Map of how to get from Berkshires to Chicago.ExpandLaunch map view
  • Distance: 772.7 mi
  • Duration: 4h 19m

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

Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily. Tickets cost $260–550 and the journey takes 18h 30m. Alternatively, you can take a vehicle from Berkshires to Chicago Bus Station via Williamstown, Port Authority Bus Terminal, and New York Midtown in around 28h 58m.

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