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

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There are 8 ways to get from Chicago to Williamstown by plane, bus, train (Amtrak), bus (Flixbus), car, or train

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 Chicago Midway International Airport to Albany County Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the bus from Albany International Airport to Green Mountain Community Bus Terminalbus bus
    7h 34m
    $152–768

  2. Fly Chicago O'Hare International Airport to Bradley International Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Springfield to Pittsfield Amtrak Stationtrain train
    9h 43m
    $102–465

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    19h 25m
    $280–581

  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 1m
    $177–323

  5. Drive 842.8 mi

    1. Drive from Chicago to Williamstowncar car 842.8 mi
    14h 48m
    $154–223

  6. Fly Chicago O'Hare International Airport to Albany County Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the bus from Albany International Airport to Green Mountain Community Bus Terminalbus bus
    8h 1m
    $122–618

  7. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Springfield to Pittsfield Amtrak Stationtrain train
    9h 12m
    $128–565

  8. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Pittsfield Amtrak Stationtrain train
    10h 40m
    $270–703

Chicago to Williamstown by train and bus (Amtrak)

Calendar7Weekly Services
Duration19h 25mAverage Duration
Ticket$280Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Williamstown.ExpandLaunch map view
  • Distance: 791.1 mi
  • Duration: 7h 34m

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

Amtrak operates a train from Chicago Union Station to Pittsfield Amtrak Station once daily. Tickets cost $270–600 and the journey takes 18h. Alternatively, you can take a bus from Chicago Bus Station to Williamstown via New York Midtown and Port Authority Bus Terminal in around 23h 1m.

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