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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 40m
    $249–778

  2. Bus

    cheapest
    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 N2640
    26h 58m
    $148–327

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    19h 13m
    $256–1,154

  4. Drive 853.6 mi

    1. Drive from Berkshires to Chicagocar car 853.6 mi
    15h 7m
    $156–225

  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
    5h 1m
    $219–578

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

Calendar20Weekly Planes
Duration4h 35mAverage Duration
Ticket$104Cheapest 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 $210–1,100 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 26h 58m.

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