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

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There are 7 ways to get from Lenox to Chicago by bus, plane, train (Amtrak), 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 Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    7h 30m

  2. Drive 854.4 mi

    cheapest
    1. Drive from Lenox to Chicagocar car 854.4 mi
    14h 42m
    $156–226

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h

  4. Bus

    1. Take the bus from Lenox to Port Authority Bus Terminalbus bus Williamstown
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    25h 21m

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

    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    7h 58m

  6. 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 44m

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

    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 14m

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

Calendar35Weekly Planes
Duration4h 14mAverage Duration
Ticket$121Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily, and the journey takes 18h 30m. Alternatively, you can take a bus from Lenox to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 25h 21m.

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