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How to get fromWilliamstown to Chicagoby bus, plane, train (Amtrak), bus (Flixbus), car, or train

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There are 7 ways to get from Williamstown to Chicago by bus, plane, 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. Bus to Albany County Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Green Mountain Community Bus Terminal to Albany International Airportbus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    7h 6m
    $120–618

  2. Train to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    9h 23m
    $92–404

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 15m
    $274–611

  4. Bus

    1. Take the bus from Williamstown to Port Authority Bus Terminalbus bus Williamstown
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 51m
    $175–328

  5. Drive 843.2 mi

    1. Drive from Williamstown to Chicagocar car 843.2 mi
    14h 48m
    $154–223

  6. Bus to Albany County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Green Mountain Community Bus Terminal to Albany International Airportbus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    7h 35m
    $106–498

  7. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    8h 49m
    $102–464

Williamstown to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 15mAverage Duration
Ticket$274Cheapest Price
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Questions & Answers

Map of how to get from Williamstown to Chicago.ExpandLaunch map view
  • Distance: 789.4 mi
  • Duration: 7h 6m

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

Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily. Tickets cost $270–600 and the journey takes 18h 30m. Alternatively, you can take a bus from Williamstown to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 22h 51m.

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