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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)plane plane MDW - ALB
    2. Take the taxi from Albany-Airport-ALB to Berkshirestaxi taxi
    4h 54m
    $282–935

  2. Drive 853.3 mi

    cheapest
    1. Drive from Chicago to Berkshirescar car 853.3 mi
    15h 11m
    $156–225

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    18h 43m
    $332–612

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to Williamstownbus bus New York
    23h 38m
    $200–343

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the taxi from Albany-Airport-ALB to Berkshirestaxi taxi
    5h 25m
    $252–785

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

Calendar32Weekly Planes
Duration2h 48mAverage Duration
Ticket$145Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Berkshires.ExpandLaunch map view
  • Distance: 773.3 mi
  • Duration: 4h 54m

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 $280–600 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 23h 38m.

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