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

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There are 6 ways to get from Chicago to Berkshires by plane, taxi, train (Amtrak), bus (Greyhound), car, or bus (Flixbus)

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
    $292–985

  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
    $273–558

  4. Bus via Brook Park

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Albany Bus Terminal, NYbus bus
    3. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    22h 34m
    $175–317

  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 11m
    $252–785

  6. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from New York to Pittsfieldbus bus Bz 0712
    28h 4m
    $220–352

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

Calendar40Weekly Planes
Duration2h 47mAverage Duration
Ticket$149Cheapest 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 $220–550 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Berkshires via Cleveland Bus Station, Albany Bus Terminal, NY, Pittsfield, Intermodal Center, and Center St. in around 22h 34m.

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