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How to get fromChicago to Berkshiresby plane, taxi, train (Amtrak), bus (Flixbus, Greyhound) 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, Greyhound), 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 51m
    $252–835

  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
    $288–586

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Port Authority Bus Terminalbus bus 108
    3. Take the bus from Port Authority Bus Terminal to Williamstownbus bus
    23h 31m
    $181–345

  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 21m
    $228–655

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

Calendar44Weekly Planes
Duration3h 15mAverage Duration
Ticket$117Cheapest 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 $240–550 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Berkshires via Newark Penn Station, Port Authority Bus Terminal, and Williamstown in around 23h 31m.

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