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

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There are 5 ways to get from Berkshires to Chicago by taxi, plane, train (Amtrak), bus (Greyhound, 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
    $269–878

  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
    $286–604

  4. Bus

    1. Take the bus from Williamstown to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus bus 108
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    23h 32m
    $183–347

  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
    $234–638

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

Calendar31Weekly Planes
Duration4hAverage Duration
Ticket$125Cheapest Price
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Questions & Answers

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 $240–550 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 Newark Penn Station in around 23h 32m.

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