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How to get fromChicago to Berkshiresby plane, taxi, train (Amtrak), bus (Flixbus) or car

Find Transport to Berkshires

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There are 5 ways to get from Chicago to Berkshires by plane, taxi, 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. Fly from Chicago Midway International Airport, taxi

    best
    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)planeMDW - ALB
    2. Take the taxi from Albany-Airport-ALB to Berkshirestaxi
    4h 50m
    $262–885

  2. Train (Amtrak)

    cheapest
    1. Take the train from Chicago Union Station to Pittsfield Amtrak StationtrainLake Shore Limited
    18h 43m
    $125–311

  3. Bus

    1. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    2. Take the bus from Port Authority Bus Terminal to WilliamstownbusNew York
    26h 43m
    $159–375

  4. Drive 853.9 mi

    1. Drive from Chicago to Berkshirescar853.9 mi
    15h 2m
    $156–226

  5. Fly from Chicago O'Hare International Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)planeORD - ALB
    2. Take the taxi from Albany-Airport-ALB to Berkshirestaxi
    5h 22m
    $342–735

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

Calendar22Weekly Planes
Duration2h 34mAverage Duration
Ticket$126Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Chicago Union Station to Pittsfield Amtrak Station once daily. Tickets cost $75–260 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Berkshires via New York Midtown, Port Authority Bus Terminal, and Williamstown in around 26h 43m.

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