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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
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)planeALB - MDW
    4h 24m
    $249–778

  2. Bus

    cheapest
    1. Take the bus from Williamstown to Port Authority Bus TerminalbusWilliamstown
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    26h 57m
    $153–337

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union StationtrainLake Shore Limited
    19h 13m
    $266–354

  4. Drive 853.6 mi

    1. Drive from Berkshires to Chicagocar853.6 mi
    15h
    $156–225

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

    1. Take the taxi from Berkshires to Albany-Airport-ALBtaxi
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)planeALB - ORD
    5h 1m
    $349–728

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

Calendar30Weekly Planes
Duration3h 43mAverage Duration
Ticket$108Cheapest 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 $220–300 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 57m.

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